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Selling Your Business? What Owners Need to Know About Taxes Before a Sale

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When owners research selling a business, taxes are usually the first thing they focus on. But the number that matters most is what lands in your pocket after taxes. A $2 million deal can produce very different results depending on your entity type, deal structure, and how the purchase price is allocated.

Key Takeaways

  • The sale price isn’t what you keep. Deal structure, entity type, and purchase price allocation can swing the after-tax result by hundreds of thousands of dollars.
  • Asset sale versus stock sale is the biggest tax fork in the road. Especially for C-corp owners, where double taxation can materially reduce what the seller takes home.
  • The biggest planning wins happen years before the sale. QSBS qualification, entity changes, and pre-sale charitable strategies all need lead time that disappears once the LOI is signed.
  • State taxes can materially increase total tax. Residency, source-state rules, and state QSBS conformity all need their own analysis.

Do You Pay Capital Gains Tax When Selling a Business?

Usually, yes, but not every dollar from the sale is taxed the same way.

The IRS treats a business sale as a sale of separate assets rather than a single transaction, which means each piece of the deal can fall into a different tax category.

Some assets receive favorable long-term capital gains treatment. The most common example is goodwill, which is the value of the business beyond its physical assets: the brand, the customer relationships, the reputation, the workflows that make the company worth more than the sum of its equipment and inventory.

Other assets are taxed less favorably. Inventory and receivables produce ordinary income. Depreciated equipment can trigger depreciation recapture, also taxed at ordinary rates. The mix of ordinary and capital gain in the final tax bill depends on entity type, deal structure, tax basis, and how the purchase price is allocated across asset categories. State taxes can shift the result further.

For most owners, that leads to an uncomfortable truth: the sale price is only half the story.

Asset Sales and Stock Sales Are Taxed Differently

If you are selling a small business, one of the biggest tax forks in the road is whether the buyer acquires assets or stock (or ownership interests).

The simplest way to think about it

Deal Structure
Common Seller Tax Result
Why Sellers Often Care

Asset sale

Mix of ordinary income and capital gain

Some proceeds may be taxed at higher rates

Stock sale

More likely to be capital gain at owner level

Cleaner reporting, often better after-tax result

C corp asset sale

Potential corporate tax plus shareholder tax

Can materially reduce what the seller keeps

In an asset sale, the buyer purchases the business’s individual assets: equipment, inventory, contracts, customer relationships, and goodwill. From the seller’s perspective, this creates a mixed tax result:

  • Inventory and receivables produce ordinary income.
  • Depreciated equipment triggers depreciation recapture, taxed at ordinary rates.
  • Real estate and certain business property receive Section 1231 treatment.
  • Goodwill and other intangibles receive long-term capital gains treatment.

In a stock sale, the buyer purchases shares of the company or ownership interests directly. The seller reports the gain at the owner level, and more of it typically gets capital gains treatment. The reporting is usually cleaner, and for C-corp owners specifically, a stock sale often avoids the double taxation that an asset sale creates: once at the corporate level when assets are sold, and again when cash is distributed to shareholders.

Why this becomes a negotiation. Buyers usually prefer asset deals because they get a step-up in basis and future depreciation benefits. Sellers usually prefer stock sales when possible, and prefer asset sales structured with more value allocated to goodwill when stock isn’t available. The deal structure is rarely a default. It’s the result of a negotiation that the seller’s tax outcome depends on.

A $2 Million Business Sale Example: What the Seller Keeps

Let’s use a federal-only illustration for a small business sold for $2,000,000. We will ignore state taxes and transaction fees so the comparison stays simple.

Scenario assumptions

  • The business is a C corporation
  • Sale price: $2,000,000
  • Shareholder stock basis: $100,000
  • Corporation’s inside asset basis: $400,000
  • Assumed federal corporate tax rate: 21%
  • Assumed shareholder capital gains rate: 20%
  • Assumed Net Investment Income Tax: 3.8%

Scenario 1: Stock sale

In a stock sale, the owner sells shares directly.

  • Sale price: $2,000,000
  • Less stock basis: $100,000
  • Taxable gain: $1,900,000
  • Federal tax at 23.8%: $452,200
  • After-tax proceeds to seller: $1,547,800

Scenario 2: Asset sale

In an asset sale, the corporation sells assets first.

  • Sale price: $2,000,000
  • Less inside asset basis: $400,000
  • Corporate taxable gain: $1,600,000
  • Corporate tax at 21%: $336,000
  • Cash left after corporate tax: $1,664,000

Then the corporation distributes the remaining cash to the shareholder.

  • Distribution amount: $1,664,000
  • Less stock basis: $100,000
  • Shareholder taxable gain: $1,564,000
  • Shareholder tax at 23.8%: $372,232
  • After-tax proceeds to seller: $1,291,768

The difference

Example

After-tax proceeds

Stock sale

$1,547,800

Asset sale

$1,291,768

Seller difference

$256,032 less in the asset sale

That is the kind of gap business owners need to understand before they negotiate the purchase agreement.

Now, if your company is an LLC or S corporation, the math may not look exactly like this because you may not have the same corporate-level tax layer. But the core lesson still holds: deal structure changes what you keep. Even in a pass-through entity, an asset sale can shift more of the proceeds toward ordinary income, depreciation recapture, or less favorable allocation buckets.

How to Reduce or Defer Taxes Before the Sale Closes

You can’t make capital gains disappear, but you can often reduce, defer, or re-characterize them.

1. Negotiate purchase price allocation carefully

In an asset sale, the buyer and seller agree on a total price and then split that price across asset categories. The split is reported on Form 8594, which both parties sign and file. Each category is taxed differently, which means the same $2 million sale can produce a meaningfully different tax bill depending on how the price is allocated.

The categories that matter most:

Inventory

Inventory is taxed as ordinary income. For most sellers, this is the worst tax outcome on the spectrum. Allocating heavily to inventory is bad for the seller and useful for the buyer.

Furniture, fixtures, and equipment (FF&E)

These trigger depreciation recapture to the extent the assets have been depreciated. The recaptured amount is taxed at ordinary rates. For a business that has fully depreciated its equipment, almost the entire allocation to FF&E becomes ordinary income.

Customer lists, non-compete agreements, and consulting agreements

Non-compete agreements and consulting agreements generally produce ordinary income to the seller. Customer lists and customer-based intangibles may receive capital-gain treatment depending on the structure of the sale and the underlying facts.

Real property

Receives Section 1231 treatment, which is generally favorable: gains can be capital gain, losses can be ordinary.

Goodwill

Receives long-term capital gain treatment. For most sellers, this is the best category to allocate value to. Buyers can also amortize goodwill over 15 years, so they don’t lose anything by agreeing to a goodwill-heavy allocation, but they may push back if they want faster write-offs from FF&E or non-compete agreements. However, there may be buyer-specific constraints such as time value of deductions, buyer tax attributes, and negotiated economics.

Where the negotiation actually happens.

The IRS requires the allocation to be reasonable. Both parties have to use the same numbers on Form 8594, so the split is binding. But within “reasonable,” there is real room.

A business with $300,000 of fully depreciated equipment, $1.5 million of goodwill, and $200,000 of inventory could see those numbers shift by tens or hundreds of thousands, depending on how each side argues their valuation.

The seller’s leverage is highest before the LOI is signed. Once allocation language is in the letter of intent, it becomes harder to renegotiate. Sellers who wait until the purchase agreement to think about allocation usually accept whatever the buyer’s accountant proposed.

The single most important move: model the after-tax proceeds under the buyer’s proposed allocation before you sign anything. If you don’t like the math, propose a different allocation in the LOI itself. The buyer’s tax position is often less affected by reallocation than the seller’s, which means there is often room to negotiate without changing the buyer’s economics meaningfully.

2. Consider whether a stock sale is realistic

For C-corp owners, the C-corp example above shows the math. A stock sale can produce hundreds of thousands more in after-tax proceeds. Buyers usually resist because asset purchases give them better tax benefits, so the negotiation becomes economic. Sometimes a seller accepts a slightly lower gross price for a meaningfully better after-tax outcome.

3. Explore installment sale treatment

As the SBA notes, an installment sale can spread gain recognition across more than one tax year when at least one payment is received later. That may help smooth the tax impact, although it does not work the same way for every asset type, and it introduces buyer-credit risk.

How the math actually changes:

If you sell a $2 million business with $1.6 million of gain and receive the entire price at closing, the gain is recognized in one year. The seller’s marginal capital gains rate, including the 3.8% Net Investment Income Tax, applies to the full amount in that year. For a high-income seller, that pushes the gain into the 23.8% federal rate.

If the same seller takes $500,000 at closing and four annual payments of $375,000, only the gain attributable to each year’s payment is recognized. The seller may stay in lower brackets in years when other income is reduced (often after they stop working in the business). Interest on the note is taxed as ordinary income, but the principal portion of each payment retains its capital gain character.

The risk

An installment sale is, in effect, seller financing. If the buyer’s business runs into trouble, the seller can lose principal payments and may have to foreclose on the company they just sold. The IRS also imputes market-rate interest on the note, which is taxed as ordinary income on top of the gain.

What doesn’t qualify:

Inventory and receivables can’t be reported on the installment method. Depreciation recapture is recognized in the year of sale regardless of payment timing. For sellers whose deal is heavy on these categories, installment treatment provides less benefit than the headline math suggests.

4. Review qualified small business stock rules

In some cases, owners of eligible qualified small business stock (QSBS) may be able to exclude some or all of the gain, subject to strict requirements around original issuance, holding period, business type, and asset limits. The IRS publication on investment income and expenses discusses Section 1202 and related QSBS rules.

Who qualifies:

  • The company must be a domestic C corporation when the stock was issued, and remain a C corp for substantially all the holding period.
  • The stock must have been originally issued to the seller (not bought from another shareholder).
  • The company’s gross assets must have been below the threshold at the time the stock was issued. For stock issued before July 4, 2025, the threshold is $50 million. For stock issued after that date, the threshold is $75 million. (Thresholds/dates may change.)
  • The seller must have held the stock for at least five years before the sale (for stock issued before July 4, 2025).
  • The company must be engaged in a qualified trade or business. Most operating businesses qualify. Service businesses (law, health, consulting, financial services, performing arts, athletics) generally don’t.

The exclusion ceiling:

The maximum exclusion is the greater of $15 million in lifetime gain per taxpayer per company (for stock issued after July 4, 2025), or 10 times the seller’s original basis. For pre-OBBBA stock issued before July 4, 2025, the cap is $10 million instead. For most founders, the dollar cap is the binding figure, but for owners who put significant capital in, the 10x basis alternative can be much higher. A founder who put $2 million into the company can exclude up to $20 million in gain on sale.

Why most owners miss it:

QSBS rules reward planning that happens at company formation, years before a sale. The C-corp election has to be in place at issuance. Owners who converted from an S-corp to a C-corp at some point can sometimes still qualify, but only for the gain accrued after the conversion.

State conformity:

Most states conform to the federal QSBS exclusion, but a few don’t. California, for example, eliminated state-level QSBS treatment in 2013, so a California seller still pays state tax on the excluded gain. Other states like Alabama and Pennsylvania also have their own rules. State conformity should be checked early.

If you’re more than two years from a sale and your company is a C corp under the asset thresholds, this is a conversation worth having now.

5. Consider pre-sale charitable planning

If charitable giving is already part of your goals, donating appreciated shares before a sale can be more tax-efficient than giving cash after the deal closes. This is one of those strategies that usually needs to happen before the sale becomes a fait accompli.

An illustration:

Suppose you plan to give $500,000 to charity around the time of a $5 million sale. If you sell first and donate cash, you pay capital gains tax on the full $5 million sale, then write a check from the after-tax proceeds. The deduction reduces your tax bill, but only on the after-tax amount.

If you donate $500,000 of pre-sale stock to a donor-advised fund, the fund sells the stock when the deal closes and receives the full $500,000 tax-free. You receive a $500,000 charitable deduction and never paid capital gains tax on the donated portion. The combined effect can save the seller well over $100,000 versus the cash-after-sale approach. Results may vary and may be materially lower depending on limitations and state tax treatment.

6. Get estate and liquidity planning in place

A sale can turn an illiquid business into a large cash balance quickly. If your exit is tied to retirement or a family legacy goal, this planning should happen before the money hits your account.

Mistakes to Avoid

A lot of business owners do not miss because they made one dramatic error, but because they waited too long.

Common problems include locking in the letter of intent before modeling after-tax proceeds, ignoring allocation language, assuming all proceeds are capital gain, and overlooking state taxes.

The practical question is not “How do I pay no tax when I sell my business?” The better question is: What structure, timing, and planning steps could help me keep more of what I built?

That framing leads to better decisions.

The Bottom Line for Business Owners

Selling a business is often a once-in-a-lifetime liquidity event. It can fund retirement, create generational wealth, or support future giving. It can also trigger a bigger tax bill than expected if the structure isn’t thought through carefully.

The biggest planning wins happen years and months before closing.

If you want help fitting a business sale into your broader financial picture, SKY Investment Group is here to help. 

SKY Investment Group, LLC is an SEC registered investment advisor. Being registered with the SEC does not imply any specific level of skill or training.

Neither SKY Investment Group, LLC nor Aspen provide tax or legal advice—please contact a professional for advice in such matters.

Investing involves the risk of loss, including the risk of loss of the entire investment. Diversification does not ensure a profit or protect against a loss.

Contact us today to start a conversation

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Benefits of Donor-Advised Funds: Why More Families Are Choosing a DAF

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According to the National Philanthropic Trust, donor-advised funds held $251.52 billion in charitable assets across nearly 1.8 million accounts in 2023, a nearly 10% increase in assets from the prior year. That growth is due to multiple contributing factors. Donor advised funds offer flexibility, simplicity, and a powerful way to build a giving legacy that reflects your values.

Key Takeaways

  • DAFs offer an immediate tax deduction when you contribute, even if you recommend grants to charities months or years later.
  • They mitigate capital gains taxes by donating appreciated securities directly to your DAF.
  • One account simplifies all your giving, replacing stacks of receipts with a single, organized record.
  • You can name successor advisors to involve children and grandchildren in philanthropy endeavors.
  • DAFs often offer lower cost and less complexity than a private foundation, with stronger privacy protections.

What Is a Donor Advised Fund?

A donor advised fund is a charitable giving account housed within a 501(c)(3) sponsoring organization. You make an irrevocable contribution to the fund, receive an immediate tax deduction, and then recommend grants to qualified charities over time. Think of it as a charitable savings account: your dollars go in, they can grow tax-free through investments, and you direct where the money ultimately goes.

The sponsoring organization handles administration, grant processing, and tax reporting, while you retain advisory privileges over when and where grants are made. The IRS recognizes DAFs as a specific type of charitable vehicle under the Internal Revenue Code, and contributions qualify for the same deductions as gifts to any public charity.

1. Tax Benefits of a DAF

The tax benefits of a DAF are among the most compelling reasons families choose this vehicle. When you contribute cash to a donor advised fund, you can deduct up to 60% of your adjusted gross income (AGI) in that tax year. For appreciated assets like stocks or mutual funds, the deduction limit is up to 30% of AGI. If your contribution exceeds those limits, you can carry forward the unused deduction for up to five additional years. It’s important to note that charitable contributions to a DAF are irrevocable charitable gifts. Once donated, the assets become the property of the sponsoring organization, and the donor retains advisory privileges only.

When appreciated securities are contributed directly, you also avoid the capital gains tax that would have been owed if the assets were sold first — a significant benefit for families holding long-term positions with substantial unrealized gains.

After the gift is made, the assets can remain invested in the fund on a tax-free basis, with the funds available to support future charitable grants over time. That combination may make DAFs one of the most tax-efficient vehicles for charitable giving. 

2. Flexibility and Control Over Your Donation

One of the standout benefits of a donor advised fund is the freedom to give now and decide later. You lock in your charitable deduction the year you contribute, but there’s no deadline for recommending grants.

Many DAFs also accept a wide range of asset types beyond cash. Some sponsors may accept publicly traded stock, cryptocurrency, real estate, and other complex assets. This flexibility makes it easier to align your charitable giving with your broader financial plan without liquidating holdings at an inconvenient time.

Donors also retain control over how their gifts are presented to recipient organizations. Many families appreciate the option to recommend grants anonymously, allowing the sponsoring organization to process the donation without revealing the donor’s identity to the charity. 

3. A Simplified Giving Strategy

Instead of tracking dozens of individual contributions to different organizations, one account consolidates everything. Your sponsoring organization provides a single tax receipt for your contributions, and many online giving dashboards show every grant you’ve ever recommended.

This simplicity is especially valuable for families with charitable endowments or multiple giving interests. Rather than managing separate relationships with each nonprofit, your DAF becomes the central hub for your entire charitable strategy.

4. Building a Charitable Legacy for Your Family

Beyond the immediate financial advantages, a donor advised fund is a remarkable tool for multi-generational philanthropy. By naming successor advisors, families can involve future generations in grant decisions and pass on a lasting culture of giving.

Many families use their DAF as a way to teach younger generations about giving. Involving your kids in grant decisions, discussing which organizations align with your family’s mission, and watching the fund’s impact together can shape how your children and grandchildren think about generosity for the rest of their lives.

From an estate planning perspective, assets in your DAF pass outside your taxable estate, generally, because the contribution is irrevocable (individual estate-tax results vary). This integration with your broader wealth plan makes DAFs a natural fit for families working with an advisor to coordinate giving, investing, and legacy planning. At SKY Investment Group, we see families use DAFs as a cornerstone of strategies that connect today’s financial decisions to tomorrow’s impact.

5. Low Cost and Efficiency

Many DAF sponsors, such as Fidelity Charitable, charge an administrative fee, often around 0.60% annually on a tiered basis, plus the underlying investment expenses of the selected portfolio. Because the sponsoring organization handles compliance, recordkeeping, tax reporting, and grant processing, donors typically do not need to manage legal setup, audits, or ongoing administrative tasks.

This simplicity is one reason many families choose a DAF instead of establishing a private foundation.

DAFs vs. Private Foundations

For families considering a more structured approach to philanthropy, the choice often comes down to a donor advised fund or a private foundation. Here’s how they compare:

Feature
Donor Advised Fund
Private Foundation

Startup cost

$0 to minimal depending on sponsor

Legal fees reach the thousands

Ongoing admin

Handled by sponsoring org

Board meetings, audits, tax filings

Tax deduction (cash)

Up to 60% of AGI

Up to 30% of AGI

Tax deduction (appreciated assets)

Up to 30% of AGI (FMV)

Up to 20% of AGI (cost basis)

Annual distribution requirement

None

5% of assets annually

Privacy

Grants can be anonymous

Public tax returns (Form 990-PF)

Control

Advisory privileges

Full legal control; can hire staff

For many families, a DAF delivers the higher deduction limits, lower costs, and greater privacy they need without the administrative burden of running a foundation. Private foundations make sense for those who want direct operational control or plan to employ staff for charitable programs. 

Is a Donor-Advised Fund Right for You?

The benefits of a donor advised fund apply most strongly in a few key scenarios.

If you’re experiencing a high-income year, selling a business, receiving a large bonus, or approaching retirement with concentrated stock positions, a DAF can let you capture a significant tax deduction now while distributing grants thoughtfully over time. 

If you want to involve your family in giving and create a shared philanthropic identity across generations, a DAF provides the structure to do that without the complexity of a foundation. And if you simply want an easier way to organize your giving, a single DAF account can replace a scattered approach with one streamlined plan. 

Frequently Asked Questions

Can I use a DAF to support international charities?

Yes, but with an important caveat. Your DAF’s sponsoring organization must verify that the international recipient qualifies under IRS guidelines. Most large sponsors have established processes called “expenditure responsibility” or “equivalency determination” to vet foreign nonprofits. This may take additional time compared to domestic grants.

What happens to my DAF when I pass away?

You designate successor advisors (often a spouse, children, or trusted family members) who inherit advisory privileges over the fund. If no successors are named, most sponsoring organizations will distribute the remaining assets to charities you’ve previously supported or to a general charitable pool.

Are there minimum contribution requirements for a DAF?

Minimums vary by sponsoring organization. Some national sponsors such as Fidelity Charitable accept initial contributions as low as $0 with no minimum grant size, while others such as Vanguard Charitable require $5,000 or $25,000 to open an account. Community foundations may have different thresholds. Your financial advisor can help identify a sponsor whose minimums align with your giving plans.

Can I change the charities I support through my DAF?

There’s no obligation to continue funding the same organizations year after year. You can recommend grants to any qualified 501(c)(3) at any time, shift your focus to new causes, or respond to emerging needs, subject to sponsor approval and policies. This adaptability is one of the core reasons families prefer a DAF over making large, irrevocable gifts directly to a single organization.

SKY Investment Group, LLC is an SEC registered investment advisor. Being registered with the SEC does not imply any specific level of skill or training.

Neither SKY Investment Group, LLC nor Aspen provide tax or legal advice—please contact a professional for advice in such matters.

Investing involves the risk of loss, including the risk of loss of the entire investment. Diversification does not ensure a profit or protect against a loss.

Contact us today to start a conversation

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Financial Planning for the Cost of Long-Term Care: Strategies to Prepare the Entire Family

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Few families look forward to discussing long-term care. But being financially prepared for the possibility of needing care can provide something invaluable: clarity, financial protection, and peace of mind for the entire family.

Whether you’re planning for yourself or helping a parent navigate these decisions, this guide outlines the key considerations.

Key Takeaways

  • Start planning early, ideally in your 50s or earlier, before health changes limit your options.
  • Involve your family in the conversation so everyone understands your wishes and the financial plan.
  • Organize essential legal documents such as powers of attorney, advance directives, and beneficiary designations.
  • Explore multiple funding strategies for long-term care, including insurance, self-funding, and Medicaid planning.
  • Work with a trusted financial advisor who can integrate long-term planning with estate, tax, and retirement strategies.

Long-Term Care Costs Impact the Whole Family

According to the Administration for Community Living, someone turning 65 today has a nearly 70% chance of needing some form of long-term care services and support in their remaining years, for an average duration of three years. Long-term care services include medical and non-medical care for people with a chronic illness or disability. Typically, long-term care services assist people with daily living activities such as dressing, bathing, and using the bathroom.

Without a clear plan, families often find themselves making rushed decisions: draining savings, taking on debt, or facing difficult disagreements during an already emotional time. The financial toll compounds quickly.

End of life financial planning is an act of love and consideration, not morbidity. It tells your family: “I cared enough to make this easier for you.” By addressing these issues early, you can reduce uncertainty and help ensure your wishes are understood.

Understanding the Real Cost of Long-Term Care

Many families assume Medicare will cover their long-term care expenses. In reality, Medicare provides limited skilled nursing coverage following a hospital stay, but it does not cover for the custodial care that makes up the majority of long-term care needs.

Here’s what the costs actually look like today, based on data from ACL.gov and the Genworth and CareScout 2024 Cost of Care Survey:

Type of Care
Approximate Monthly Cost
Notes

Nursing Home (Private Room)

$9,500 – $10,000

Highest level of medical supervision

Nursing Home (Semi-Private)

$8,500 – $9,000

Shared room; still significant cost

Assisted Living Facility

~$4,800

National median; varies widely by region

In-Home Health Aide

$5,300 – $6,500

Depends on hours and level of care needed

Multiply any of these figures by three years (the average duration of care), and the potential cost ranges from $170,000 to $360,000 or more.

Regional variation matters as well. Costs in the Northeast and West Coast often exceed national medians, which can significantly affect long-term planning.

Essential Legal and Financial Documents to Organize

Effective long-term care planning starts with getting the right documents in place, ideally well before they’re needed.

Power of Attorney

A financial power of attorney allows a trusted person to manage your financial affairs if you become unable to do so. This may include paying bills, managing investments, or handling real estate transactions.

A healthcare power of attorney (sometimes called a healthcare proxy) authorizes someone to make medical decisions on your behalf. These are separate documents, and both are typically necessary.

Advance Directive

An advance directive (sometimes called a living will) outlines out your preferences for medical treatment if you cannot communicate them yourself. This may include decisions about resuscitation, ventilator use, and palliative care. 

Without clear instructions, families may be forced to make difficult medical decisions without knowing your wishes.

Wills and Trusts

Understanding the difference between a will and a living trust is also important.

A will goes through probate, a court-supervised process that can take months and become public record. A living trust allows your assets to pass directly to beneficiaries, often more quickly and privately. Neither is universally “better”; the right choice depends on your estate’s complexity, your state’s probate laws, and your family’s needs.

Two often-overlooked items are beneficiary designations on retirement accounts, life insurance policies, and annuities. 

If you haven’t reviewed these recently, outdated designations could unintentionally send assets to an ex-spouse or a deceased relative’s estate. A HIPAA authorization form allows your family members to access your medical information, which is essential for coordinating care.

Strategic Estate Planning

One more critical concept: step-up in basis. If you transfer appreciated assets to your children before death, they inherit your original cost basis and may face a larger capital gains tax when they sell. If those same assets pass at death, they generally receive a stepped-up basis equal to the current market value at the time, potentially reducing or eliminating capital gains taxes. Step-up rules have exceptions and can change, and outcomes depend on the asset type, state law, and taxpayer’s situation.

Premature asset transfers, while well-intentioned, can backfire significantly. Consult a tax professional before making any such moves.

Speak with an Estate Planning Specialist

Long-Term Care Insurance and Other Funding Strategies

There is no single right way to pay for long-term care services. The best strategy depends on your health, assets, family circumstance, and risk tolerance. Here are the primary options:

Traditional long-term care insurance pays a daily or monthly benefit to help cover care costs. Premiums are generally lower when you purchase coverage in your 50s while still healthy. However, premiums may increase over time, and if you never need care, the premiums are not recoverable. 

Hybrid Life/LTC policies combine life insurance with long-term care benefits. If you need care, the policy provides coverage. If not, beneficiaries receive a death benefit. These policies often require a larger upfront premium but address the “use it or lose it” concern of traditional insurance.

Self-funding means setting aside dedicated assets to cover potential care costs. This approach works for families with substantial savings, but it requires disciplined planning and realistic projections and carries the risk of underestimating the total cost or the duration of care needed.

Medicaid planning is relevant for families with more modest resources. Eligibility requires meeting strict income and asset limits. Qualifying often involves a spend-down process, where countable assets are reduced to meet eligibility thresholds. Because Medicaid rules include a five-year lookback period, planning well in advance is important. 

Each of these strategies carries trade-offs. A financial advisor who understands long-term care needs can help you weigh the costs, risks, and benefits in the context of your complete financial picture.

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Legacy Considerations

Without a plan, extended care can force families to draw down retirement accounts more quickly than expected, liquidate investments during unfavorable markets, or sell illiquid assets at the wrong time. This type of disruption can affect current lifestyle and reduce what remains for a surviving spouse, heirs, or charitable goals.

A thoughtful financial strategy focuses on three key priorities:

  1. Protecting the healthy spouse.
    If one partner needs care, the other may still need decades of income. Planning should ensure that essential living expenses remain secure even if significant care costs arise.
  2. Managing taxes and withdrawal strategy.
    How care costs are funded matters. Drawing from taxable accounts, retirement plans, or insurance benefits may help minimize tax spikes and preserve long-term portfolio growth.
  3. Maintaining liquidity and flexibility.
    Care costs often arise unexpectedly. Keeping sufficient liquid assets helps avoid forced sales of long-term investments.

Ultimately, long-term care planning often involves balancing three priorities: maintaining independence, protecting a spouse, and preserving a meaningful legacy. Integrating care planning into your broader wealth strategy helps ensure that one unexpected event doesn’t derail the financial future you’ve worked to build.

Talking to Your Family About End-of-Life Finances

Knowing what to plan is one thing. Getting your family on the same page is another. Many people avoid these conversations because they feel awkward, premature, or even morbid. However, addressing them early often prevents confusion or conflict later.

Start by discussing your values and preferences, not just your finances. What type of care would you want? What matters most to you as you age? 

When conversations focus on goals rather than numbers, they often become more constructive.

Some families find it helpful to hold a structured family meeting, possibly including a financial advisor or estate attorney. A neutral professional can help keep the conversation focused and reduce misunderstandings.

It is also helpful for family members to know:

  • where important documents are stored
  • who holds power of attorney
  • who is designated as healthcare proxy

Clear communication today can help reduce uncertainty during future health events.

Working with a Trusted Advisor

Long-term care planning affects nearly every part of your financial life: investments, taxes, estate planning, insurance, and family decisions. While it is possible to address these independently, an experienced advisor can help you identify blind spots and bring everything into a cohesive plan.

At SKY Investment Group, we help families navigate these decisions with clarity within the context of a comprehensive wealth strategy. If you’re ready to take the next step in protecting your family’s future, we’re here to help. 

Frequently Asked Questions

How do you choose between a living trust and a will?

It depends on your goals. A living trust avoids probate, keeps your estate private, and can provide for management of your assets if you become incapacitated.

A will is simpler and less expensive to create, but goes through probate. Many families use both: a trust for major assets and a pour-over will as a safety net. Your state’s probate laws and the complexity of your estate should guide the decision.

Should you update your financial plan after losing a spouse?

Yes. The loss of a spouse can significantly affect every dimension of your financial picture, from income sources, tax filing status, estate structure, and caregiving assumptions.

Beneficiary designations, powers of attorney, and healthcare directives should all be reviewed and updated. 

Meeting with an advisor soon after a loss can help ensure important decisions are made thoughtfully rather than reactively.

How much should you set aside to pay for long-term care?

Many financial plans assume a potential care reserve of $200,000 to $400,000 per person, as shown in the chart above, based on national cost estimates and typical care duration.

However, the appropriate amount depends on location, desired level of care, and whether a spouse’s financial security must also be protected.

Should you transfer assets to family members to qualify for Medicaid?

Asset transfers can create unintended tax consequences and may trigger Medicaid’s five-year lookback penalties, delaying eligibility.

In addition, gifting appreciated assets during your lifetime may eliminate the step-up in basis, increasing capital gains taxes for heirs.

Always consult a tax professional or financial advisor before making transfers.

Can long-term care planning improve tax efficiency?

Potentially. Strategies such as coordinating withdrawals across account types, donating appreciated assets, or using insurance benefits strategically may help manage tax exposure if care becomes necessary.

SKY Investment Group, LLC is an SEC registered investment advisor. Being registered with the SEC does not imply any specific level of skill or training.

Neither SKY Investment Group, LLC nor Aspen provide tax or legal advice—please contact a professional for advice in such matters.

Investing involves the risk of loss, including the risk of loss of the entire investment. Diversification does not ensure a profit or protect against a loss.

Contact us today to start a conversation

The Connecticut shoreline of Long Island Sound

What Is a Qualified Personal Residence Trust (QPRT)?

The Connecticut shoreline of Long Island Sound

For many, their home is their most valuable asset, and passing it to children without triggering a large estate tax bill can feel daunting. A qualified personal residence trust (QPRT) may provide a way to transfer your home to the next generation at a fraction of its taxable value. Here’s how it works and whether it makes sense for your family.

Key Takeaways

  • A QPRT allows you to transfer your home to heirs while continuing to live in it for a specific number of years, reducing the taxable value of the gift.
  • Higher Section 7520 interest rates can make QPRTs more tax-efficient in 2026 by shrinking the remainder interest.
  • The trust is irrevocable, meaning you permanently relinquish ownership once the term ends.
  • You must outlive the trust term for the tax benefits to apply; otherwise, the home returns to your taxable estate.
  • QPRTs work best for homeowners with high property values who are relatively young and healthy.

How a Qualified Personal Residence Trust Works

Setting up a qualified personal residence trust involves a straightforward sequence of steps, though the tax mechanics behind them are what make the strategy so powerful.

First, you (the grantor) transfer ownership of your home into an irrevocable trust. You name your children or other loved ones as beneficiaries. Then you select a term of years during which you retain the right to live in the home. This is your retained interest: the value of your continued use of the property for the duration of the term. At the end of the term, the home passes to your beneficiaries. Their share is called the remainder interest.

How a QPRT Can Help With Taxes

When you fund the QPRT, the IRS treats the transfer as a gift, but only the remaining interest counts as a taxable gift, not the home’s full fair market value. The remainder interest is calculated using the Section 7520 interest rate, your age at the time of transfer, and the length of the term you choose.

Because the IRS discounts the gift by the value of your retained interest, the taxable gift is significantly smaller than the home’s actual market value. That discount is the entire point of the strategy. Any future appreciation in the home’s value passes to your beneficiaries completely free of estate and gift tax.

After the term ends, you can still live in the home if you wish. You simply pay fair market rent to your beneficiaries, which further reduces your taxable estate by moving additional cash to the next generation.

Why Interest Rates Matter for QPRTs

The Section 7520 rate, published monthly by the IRS, plays a central role in determining how much tax you save. Think of it this way: a higher rate means the IRS assigns more value to your retained interest (your right to live in the home). As your retained interest increases, the remainder interest decreases, reducing the size of the taxable gift. 

In a low-rate environment, the math works against you because the IRS assumes your retained interest is worth less, leaving a bigger taxable gift. In today’s higher-rate environment, the calculus flips. The remainder interest shrinks, which means you can transfer the same home with a smaller hit to your gift tax exemption (rose to $15M for calendar year 2026).

For families who have been waiting for the right moment to explore a QPRT, the current interest rate landscape is worth a serious look. Even modest rate differences can translate into significant dollars in gift tax savings on a high-value residence (“savings” may reflect reduced taxable gift value and may not equal cash tax avoided).

QPRT Pros and Cons

Every estate planning tool involves tradeoffs. Here’s an honest look at both sides of the QPRT pros and cons equation.

Pros
Cons

May significantly reduce estate tax by removing the home (and its future appreciation) from your taxable estate

The trust is irrevocable: once funded, you cannot take the home back or change your mind

You continue living in the home during the trust term with no disruption to daily life

You must outlive the term; if you pass away during it, the home snaps back into your estate as if the QPRT never existed

The taxable gift is discounted, preserving more of your lifetime gift tax exemption

Beneficiaries receive your cost basis rather than a stepped-up basis, which could mean higher capital gains taxes if they sell

All future appreciation transfers to beneficiaries tax-free

You cannot refinance or take out a home equity line once the property is in the trust

Rent payments after the term further reduce your estate

Local property tax reassessments may be triggered depending on your state

Locks in today’s home value for transfer tax purposes, which may shift all future appreciation outside your estate

After the term, heirs may lose the $250k/$500k capital gains exclusion unless occupancy rules are met

QPRT Rules to Know

The IRS governs QPRTs under IRC Section 2702, and there are several QPRT rules you need to understand before moving forward.

  1. Two-trust limit. You are allowed a maximum of two QPRTs: one for your primary residence and one for a second or vacation home. Investment properties and rental homes do not qualify.
  2. Survival requirement. The grantor must survive the entire trust term for the strategy to succeed. If you die before the term ends, the home’s full fair market value is included in your estate. However, the gift tax exemption used when funding the QPRT is restored, so your estate is not taxed twice. Given this risk, term selection should be approached carefully and tailored to your age, health, and planning goals.
  3. Mortgage payments count as gifts. If there is a mortgage on the home when you transfer it, any payments you make on that mortgage while the trust is in effect are treated as additional taxable gifts to the beneficiaries.
  4. Grantor trust status. During the term, the QPRT is treated as a grantor trust for income tax purposes. That means you continue to deduct property taxes and mortgage interest on your personal return, just as you did before the transfer.
  5. Generation-skipping transfer (GST) limitation. You generally cannot allocate your GST exemption to a QPRT until the retained term ends and the remainder interest becomes possessory. If you pass away during the term, the strategy unwinds, and GST planning may need to be revisited. This limitation makes QPRTs less flexible for families intending to benefit grandchildren directly.

Is a QPRT Right for Your Family?

A QPRT may not suit every situation. It can be worth considering for families whose primary residence has significant fair market value, where the grantor has reasonable confidence in outliving a chosen trust term (based on age and health), and who are planning for multi-generational wealth transfer.

The strategy also works best as part of a broader, holistic financial plan. A QPRT does not exist in a vacuum; it connects to your overall gifting strategy, your income tax planning, and your family’s long-term goals. Getting those pieces to work together is where thoughtful guidance makes all the difference.

Frequently Asked Questions

Can you have more than one QPRT?

The IRS allows up to two QPRTs per grantor: one for a primary residence and one for a second home. Married couples can each create their own pair, potentially covering up to four properties between them.

What happens to a QPRT if you get divorced?

Divorce can complicate a QPRT significantly. If the home is subject to property division, the trust terms may conflict with a divorce settlement. Courts have handled these situations differently by state, so early coordination between your estate planning attorney and divorce counsel is essential.

Can you sell the home inside a QPRT?

You can, but the proceeds must either be used to purchase a replacement residence within 2 years or the trust must convert to a grantor-retained annuity trust (GRAT) for the remaining term. You cannot simply pocket the sale proceeds.

Does a QPRT protect assets from creditors?

A QPRT offers limited asset protection. Because the transfer is irrevocable, the home is generally outside the reach of your personal creditors after the transfer. However, if the QPRT was funded with the intent to defraud creditors, courts can unwind the transfer under fraudulent conveyance laws.

What’s the ideal QPRT term length?

There is no universal answer, but most planners recommend a term long enough to generate meaningful tax savings while short enough that you are highly likely to outlive it. A QPRT calculator can help model different scenarios based on your age, home value, and the current Section 7520 rate.

SKY Investment Group, LLC is an SEC registered investment advisor. Being registered with the SEC does not imply any specific level of skill or training.

Neither SKY Investment Group, LLC nor Aspen provide tax or legal advice—please contact a professional for advice in such matters.

Investing involves the risk of loss, including the risk of loss of the entire investment. Diversification does not ensure a profit or protect against a loss.

A group of people, athletes and members of the public, who voluntarily participated in the charity march. Group of people walking in sports, walking and jogging clothes.

Charitable Donation Limits: What Changed Under the New Tax Law?

A group of people, athletes and members of the public, who voluntarily participated in the charity march. Group of people walking in sports, walking and jogging clothes.

The One Big Beautiful Bill Act (OBBBA), signed on July 4, 2025, significantly reshaped the rules governing charitable donation limits. Whether you itemize deductions or take the standard deduction, these changes affect how much of your giving translates into tax savings starting in 2026.

Here is what you need to know to give wisely and confidently.

Key Takeaways

  • Non-itemizers get a new above-the-line deduction of $1,000 (single) or $2,000 (married filing jointly) for cash gifts to qualifying charities, effective 2026.
  • Itemizers face a new 0.5% AGI floor, meaning only charitable contributions exceeding that threshold are deductible.
  • The 60% of AGI ceiling for cash donations to public charities is now permanent, removing years of uncertainty about whether it would revert to 50%.
  • Strategic giving matters more than ever. Gift bunching, donor-advised funds, and qualified charitable distributions can help you maximize every dollar. 
  • The 5-year carry-forward rule still applies for taxpayers who itemize, so excess contributions are not lost. 

This article is for informational purposes only and does not constitute tax or legal advice. Tax laws are complex and subject to change. Please consult a qualified tax professional regarding your specific situation.

What the OBBA Changed for Charitable Donations

For years, the rules around the charitable donation limit felt like a moving target. The Tax Cuts and Jobs Act (TCJA) of 2017 nearly doubled the standard deduction, which pushed millions of taxpayers away from itemizing on Schedule A (Form 1040).

The CARES Act temporarily introduced a small above-the-line deduction for non-itemizers, but that expired after 2021. Many generous families were left wondering whether their donations still “counted” at tax time.

The OBBBA answers that question with two major changes to IRC Section 170, both effective for tax year 2026 and beyond. First, it creates a permanent above-the-line charitable deduction for non-itemizers. Second, it introduces a new 0.5% AGI floor for itemizers, which reduces the deductible amount for smaller gifts relative to income. Together, these provisions reward consistent, meaningful giving while adjusting the tax benefit for those who donate modest amounts compared to their earnings.

New Charitable Deduction for Non-Itemizers

If you have been taking the standard deduction, which rises to $16,100 for single filers and $32,200 for married filing jointly in 2026, you likely felt that your charitable gifts may not have had significant tax benefits. That changes now.

Under the OBBBA, non-itemizers can claim an above-the-line deduction of $1,000 for single filers or $2,000 for married couples filing jointly. This deduction applies only to cash contributions made to qualified 501(c)(3) organizations. Gifts to donor-advised funds and most private foundations do not qualify.

What makes this especially valuable is that the deduction is “above the line,” which means it reduces your adjusted gross income (AGI) directly. Social Security benefits become taxable once income exceeds $25,000 for single filers or $32,000 for married couples filing jointly, thresholds that have never been indexed for inflation. As a result, even a modest $1,000 to $2,000 reduction in AGI can reduce the portion of benefits subject to tax.

There are a couple of important limitations to keep in mind. This above-the-line deduction does not allow a carryforward for excess contributions. If you are single and donate $1,500 in cash, you can deduct $1,000, but the remaining $500 does not carry over to the next year. And because this deduction is limited to cash, donating appreciated stock or property will not qualify. However, those gifts may still make sense through other strategies we will discuss below.

New Limits for Itemizers: The 0.5% AGI Floor

If you do itemize your deductions, the OBBBA introduces a wrinkle that is easy to overlook. Starting in 2026, only charitable contributions that exceed 0.5% of your AGI are deductible under the new charitable contribution deduction rules.

Here is how that works in practice.

Say your AGI is $200,000. Half a percent of that is $1,000. If you donate $10,000 to your favorite charity, only $9,000 is deductible because the first $1,000 falls below the floor. For most generous donors, this floor is a relatively minor adjustment. But for families whose giving is modest relative to their income, it chips away at the deduction.

Additional Nuance for High Earners

For taxpayers in the top income bracket (tax rate 37%), the tax benefit of itemized deductions is effectively limited to a 35% rate rather than their full marginal rate. This applies to single filers with income above $640,600 and married couples filing jointly above $768,700. It is a small haircut, but worth knowing if you are planning a large gift.

On the brighter side, the OBBBA made the 60% of AGI ceiling for cash contributions to public charities permanent. Before the TCJA, this ceiling was 50%. The TCJA raised it to 60% on a temporary basis, and there had been real uncertainty about whether Congress would let it revert. That question is now settled.

Charitable Contribution Limits by Donation Type

Clients often ask: “How much can I actually deduct?” The answer depends on what you give and who you give it to. Below is a comparison of the current IRS charitable donation limits by type for use in preparing 2025 returns:

Donation Type
AGI Limit
Carryforward

Cash to public charities

60% of AGI

5 years

Long-term appreciated property to public charities

30% of AGI

5 years

Cash to private foundations

30% of AGI

5 years

Appreciated property to private foundations

20% of AGI

5 years
Conservation easements (qualified)

50% of AGI (special rules apply)

15 years

The 5-year charitable contribution carryover (for taxpayers who itemize) is worth highlighting. If your generosity exceeds the AGI ceiling in a given year, the excess does not disappear. You can carry it forward and deduct it over the next five tax years, subject to the same percentage limits. This is especially relevant for families making large one-time gifts, such as funding a charitable endowment or contributing a significant appreciated asset.

Strategies to Maximize Your Charitable Deduction

Knowing the rules is one thing. Putting them to work for your family is another. Here are strategies that can help you navigate the new landscape and make your giving go further.

Gift Bunching

The idea is simple: instead of donating the same amount every year, you concentrate two or three years of giving into a single year. In the “on” year, your total contributions push you past the standard deduction threshold, allowing you to itemize. In the “off” years, you take the standard deduction. With the new 0.5% AGI floor in play, bunching also helps ensure a larger share of your gifts clears that threshold.

Donor-Advised Funds (DAFs)

You can contribute a lump sum to a DAF in your bunching year, claim the full deduction, and then distribute grants to your chosen charities over time. Your favorite organizations still receive steady support, and you capture the maximum tax benefit. Keep in mind that contributions to DAFs do not qualify for the new non-itemizer deduction, so this strategy is for itemizers only.

Qualified Charitable Distributions (QCDs)

These remain a standout option for anyone age 70½ or older with an IRA. If all requirements are met, a QCD lets you transfer up to $108,000 directly from your IRA to a qualified charity in 2026. If the transfer is made directly, the distribution may be excluded from your taxable income (IRS Notice 2025-67). For retirees who want to support causes they love while keeping their tax picture clean, QCDs are hard to beat.

Donating appreciated securities

Donating appreciated securities instead of cash is another option. When you give stock or other assets that have grown in value and that you have held for more than a year, you avoid capital gains tax on the appreciation while receiving a deduction for the full fair market value (outcomes depend on holding period, asset type, and recipient).

What Has Not Changed?

Amid all the new provisions, several foundational rules remain exactly as they were.

Your donations must go to qualified 501(c)(3) organizations to be deductible. The IRS maintains a searchable database (Tax Exempt Organization Search) where you can verify a charity’s status before you give.

Substantiation requirements have not changed either. Any donation of $250 or more requires a written acknowledgment from the charity received at the time of the gift. For cash donations of any size, you need a record or written communication from the organization. These documentation rules are outlined in IRS Publication 526, and overlooking them is one of the most common reasons deductions get denied on audit.

The 5-year carryforward for excess charitable contributions continues to apply across all donation types (with the exception of conservation easements, which have a longer carryforward period). And QCD rules remain intact under the new law, preserving one of the most valuable tools in a retiree’s charitable toolkit.

Frequently Asked Questions

How much can you deduct in charitable contributions in 2025 versus 2026? For tax year 2025, the rules from the TCJA still apply: up to 60% of AGI for cash gifts to public charities if you itemize, with no above-the-line deduction for non-itemizers. Starting in 2026, the OBBBA adds the new $1,000/$2,000 non-itemizer deduction and introduces the 0.5% AGI floor for itemizers.

Does the new non-itemizer deduction apply to donations made through my workplace giving program? It depends on how your employer structures the program. If your payroll deduction goes directly to a qualified 501(c)(3), it should qualify. However, if it routes through a DAF or a private foundation, it will not. Check with your HR department and a tax professional to confirm.

Can I combine the non-itemizer deduction with a QCD? Yes, these are separate provisions. A QCD is excluded from income entirely and does not appear on Schedule A. The non-itemizer deduction is a separate line item that reduces AGI. If you are 70½ or older, using both can be especially effective.

What happens if the 0.5% floor costs me more than the non-itemizer deduction would give me? This is exactly the kind of scenario where running the numbers matters. Some taxpayers near the itemizing threshold may find it more advantageous to take the standard deduction plus the new above-the-line deduction rather than itemizing. A trusted financial advisor or tax professional can model both scenarios for your specific situation.

Are contributions to my church still deductible?  Yes, as long as your house of worship is a qualified 501(c)(3) organization, contributions remain deductible under the same rules. Cash gifts qualify for both the itemizer deduction and the new non-itemizer deduction (non-itemizers face separate caps and itemizers face percentage/floor limits).

Your Giving Deserves a Thoughtful Plan

It is natural to feel uncertain when the tax rules shift beneath your feet, especially when your charitable giving reflects values you have held for a lifetime. The good news is that the new law creates opportunities alongside its changes. With the right strategy, you can continue supporting the causes closest to your heart while making the most of every tax benefit available to you.

At SKY Investment Group, we help families build giving strategies that align with their financial journey and their legacy. Whether you are exploring donor-advised funds, considering QCDs, or simply want to understand how the new charitable donation limit rules affect your plan, we are here to help you think it through.

SKY Investment Group, LLC is an SEC registered investment advisor. Being registered with the SEC does not imply any specific level of skill or training.

Neither SKY Investment Group, LLC nor Aspen provide tax or legal advice—please contact a professional for advice in such matters.

Investing involves the risk of loss, including the risk of loss of the entire investment. Diversification does not ensure a profit or protect against a loss.

New England Lighthouse in Lighthouse Point Park in New Haven Connecticut

Donor Advised Fund vs. Private Foundation: Building Your Charitable Giving Strategy

New England Lighthouse in Lighthouse Point Park in New Haven Connecticut

When you’re ready to formalize your charitable giving, two vehicles often rise to the top: donor-advised funds and private foundations. Both offer meaningful tax advantages and a way to support causes you care about, but they differ significantly in cost, control, and complexity. 

Understanding how each vehicle works can help you choose the right structure—or combination of structures—for your philanthropic goals. 

Key Takeaways

  • DAFs are simpler and cheaper to start, with minimums varying significantly depending on the sponsor, while private foundations are often most practical when charitable assets approach $1 million or more, given the legal and administrative costs involved.
  • Private foundations offer full governance control and multi-generational family involvement.
  • Tax deduction limits differ significantly: DAFs allow deductions up to 60% of AGI for cash, compared to 30% for foundations.
  • You can use both together. A combined strategy lets you leverage the strengths of each vehicle.

What Is a Donor-Advised Fund?

A donor-advised fund (DAF) is a charitable giving account held at a sponsoring organization. Think Fidelity Charitable (no minimum to open an account), Schwab Charitable, or a local community foundation. You make an irrevocable contribution to the fund, receive an immediate tax deduction, and then recommend grants to qualified charities over time. The IRS defines DAFs as funds owned and controlled by the sponsoring organization, with the donor retaining advisory privileges only.

That distinction matters. Once you contribute, the sponsoring organization has legal control of the assets. You advise where grants go, but the sponsor technically has the final say. In practice, sponsors approve the vast majority of grant recommendations, but legal control of the assets ultimately rests with the sponsoring organization.

The regulatory framework for DAFs was largely established by the Pension Protection Act of 2006, which formalized rules around how these funds operate. Since then, DAFs have exploded in popularity. According to the National Philanthropic Trust 2024 DAF Report, DAF payout rates consistently have been at or exceed 20% annually, which is well above the 5% minimum that private foundations must distribute.

What makes DAFs especially appealing is their simplicity. There’s no legal entity to establish, no board to assemble, no annual filings to manage. You can open one in a day and start recommending grants almost immediately. 

What Is a Private Foundation?

A private foundation is an independent 501(c)(3) legal entity, typically structured as either a nonprofit corporation or a charitable trust. Unlike a DAF, a foundation is entirely yours to govern. You establish the board, set the mission, hire staff if needed, and make all grant decisions directly.

That independence comes with responsibility. The IRS requires private foundations to file Form 990-PF annually, disclosing finances, grants, and governance details. Board meetings must be held, investment policies maintained, and operational compliance monitored year-round.

Foundations can do things DAFs simply cannot.

  • They can grant directly to individuals, funding scholarships, hardship relief, or community programs, subject to IRS rules, without being limited to IRS-qualified charities.
  • They can hire family members as staff if structured to comply with self-dealing rules.
  • They can invest in alternative assets like private real estate or private equity.
  • They can become lasting institutions that carry a family’s philanthropic vision across generations. 

For families with the resources and the desire for hands-on involvement, a private foundation isn’t just a giving vehicle. It’s a family institution.  

Donor-Advised Fund vs. Private Foundation: Key Differences

The core differences between a DAF and a private foundation come down to five areas: control, cost, tax treatment, privacy, and administrative complexity. Here’s how they compare:

Feature
Donor-Advised Fund
Private Foundation
Legal Structure

Account at sponsoring org

Independent 501(c)(3) entity

Control

Advisory only

Full governance control

Startup Cost

Minimal (~$10K minimum)

Significant (legal fees, $1M+ typical)
Ongoing Cost

Varies. Many sponsors charge ~0.60% admin (tiered)

Varies widely. Often ~0.5%–2%+ depending on size

Tax Deduction (Cash)

Up to 60% of AGI

Up to 30% of AGI

Tax Deduction (Appreciated Assets)

Up to 30% of AGI at FMV

Up to 20% of AGI (cost basis for some non-publicly traded assets)

Annual Payout Requirement

None
5% of assets

Privacy

Anonymous donations possible

Public (990-PF is public record)

Administrative Burden

Low — sponsor handles it

High — legal, accounting, filings

Grant Recipients

Qualified charities only

Individuals and organizations

Family Involvement

Limited

Board seats, staff roles, legacy

Both vehicles have a place in a thoughtful charitable giving strategy. The question isn’t which is better, but which fits your situation. 

Tax Benefits Compared

From a tax perspective, donor-advised funds generally offer higher deduction limits and fewer ongoing taxes than private foundations.

Contribution Type
Donor-Advised Fund
Private Foundation
Cash

Up to 60% of AGI

Up to 30% of AGI

Appreciated securities

Up to 30% of AGI (FMV)

Up to 20% of AGI (with certain non-publicly traded assets deductible at cost basis rather than fair market value)

Capital gains on donated assets
Avoided
Avoided
Ongoing tax
None

1.39% excise tax on investment income

Both vehicles allow you to donate appreciated assets without recognizing capital gains. Contributing shares directly (rather than selling and donating cash) preserves more value for charitable use.

For many donors, the higher AGI limits and absence of excise taxes make DAFs the more tax-efficient vehicle. But tax efficiency alone shouldn’t drive your decision. Control, legacy, and flexibility may outweigh the tax difference. 

Control, Flexibility, and Family Legacy

Here’s where the conversation shifts from numbers to something much deeper. A private foundation gives your family full governance control. You choose the board, often composed of family members across generations. You set the investment strategy. You decide which causes to support and how to support them.

That control extends to investment flexibility. Foundations can invest in private real estate, private equity, hedge funds, and other alternatives that most DAF sponsors won’t offer. If you want your charitable assets managed alongside a broader private client portfolio, a foundation gives you that latitude. 

Foundations can also conduct international grantmaking directly, though it requires additional compliance procedures. Many DAF sponsors offer international grant support but typically handle the required due diligence themselves.

For families who see philanthropy as a shared value and a teaching opportunity, foundations offer something irreplaceable. Younger family members can serve on the board, participate in grant-making decisions, and learn about stewardship and community responsibility in a hands-on way.

DAFs offer simplicity and ease, but the advisory nature of the relationship means you’re a recommender, not a decision-maker. For some families, that trade-off is perfectly fine. For others, the loss of direct control feels like a dealbreaker.

Cost and Administrative Requirements

The cost gap between these two vehicles can be substantial.

​​Many national sponsors, such as Fidelity Charitable, charge ~0.60% admin (tiered) plus underlying fund expenses; all-in costs vary by sponsor and investments. The sponsoring organization handles all administration, compliance, and investment management. There are no legal fees to set up, no annual filings to prepare, and no staff to pay.

With a private foundation, startup costs include legal fees for formation, drafting bylaws or trust documents, and applying for tax-exempt status. Ongoing operating costs vary depending on the size of the foundation and whether functions are handled internally or outsourced. Administrative expenses—including staff compensation, legal services, accounting, and governance costs—can represent a meaningful portion of annual spending for many foundations. 

Private foundations must hold regular board meetings, maintain detailed records of all grants and investments, and comply with a web of IRS regulations, including the 5% annual distribution requirement. Failing to distribute at least 5% of net investment assets each year can result in IRS penalties.

For families with charitable assets under $1 million, the administrative cost of a foundation often outweighs the benefits depending on individual circumstances, evaluated with tax/legal professionals. The math can change at higher asset levels, but it’s important to be realistic about the ongoing commitment.

When a Donor-Advised Fund Makes Sense

A DAF is often the right starting point if you want to formalize your giving without taking on operational complexity. You might consider a DAF when:

  • You’re making contributions starting around $10,000 or more and want immediate tax benefits.
  • You value anonymity. DAFs allow you to make grants without your name attached, which matters to many donors.
  • You want to use a bunching strategy, concentrating multiple years of charitable deductions into a single tax year to exceed the standard deduction threshold.
  • You don’t want the oversight of hiring staff, filing returns, or managing a nonprofit entity.

DAFs work well for donors who want to give strategically but stay focused on their careers and families rather than running a philanthropic organization.

When a Private Foundation Makes Sense

A private foundation becomes compelling when your charitable ambitions outgrow what a DAF can offer. If you’re contributing $1 million or more, the additional cost and complexity may be justified by the control and flexibility you gain.

Foundations make sense when:

  • You want to grant directly to individuals, funding scholarships, supporting artists, or helping community members in need. 
  • You want to hire staff to manage programs or conduct research.
  • Multiple generations of your family want to be actively involved in philanthropic decision-making.

If your investment strategy includes alternative assets and you want your charitable capital invested similarly, a foundation offers that freedom. And if building a lasting institution — one that carries your family’s name and values forward — matters to you, a foundation delivers.

Using Both Together: A Combined Strategy

You don’t have to choose one or the other. A combined strategy lets you leverage the strengths of both vehicles while mitigating their individual limitations.

Some families use the foundation as the primary vehicle for large, strategic gifts and family governance, while maintaining a DAF for smaller, more frequent donations or for grants where anonymity is preferred. The two vehicles complement each other naturally, and a combined approach may be beneficial depending on goals, costs, and governance preferences.

Building Your Charitable Giving Strategy With a Trusted Advisor

The donor-advised fund vs. private foundation decision isn’t just about tax brackets and basis points. It’s about what you want your giving to accomplish for your community, your family, and the causes closest to your heart.

At SKY Investment Group, we work with families to build charitable giving strategies that fit within a holistic wealth plan. That means looking at your tax situation, your estate plan, your family dynamics, and your philanthropic goals together, not in isolation.

Whether a DAF, a foundation, or a combination of both makes sense for you, we’ll help you think it through carefully and build something that lasts.

Ready to start a conversation? We’re here to help.

Frequently Asked Questions

Can a private foundation invest in real estate or private equity?

Yes. Unlike most DAF sponsors, private foundations have broad investment flexibility. They can hold private real estate, private equity, hedge funds, and other alternative assets.

What happens to a donor-advised fund when the account holder passes away?

Most DAF sponsors allow you to name successor advisors or designate charitable beneficiaries. The account continues under the sponsoring organization’s management, but you can plan for how advisory privileges transfer, making it a useful component of your estate plan.

Are there any restrictions on how quickly you must distribute DAF funds?

Currently, DAFs have no required payout timeline. Once you contribute, funds can remain invested indefinitely. Some legislators have proposed minimum distribution rules for DAFs, but as of now, there’s no legal requirement to recommend grants on any schedule.

Can a private foundation compensate family members who serve on the board?

Foundations can pay reasonable compensation to board members and staff, including family members. However, the IRS scrutinizes these payments closely. Compensation must be reasonable and not excessive relative to services performed, or the foundation risks self-dealing penalties.

SKY Investment Group, LLC is an SEC registered investment advisor. Being registered with the SEC does not imply any specific level of skill or training.

Neither SKY Investment Group, LLC nor Aspen provide tax or legal advice—please contact a professional for advice in such matters.

Investing involves the risk of loss, including the risk of loss of the entire investment. Diversification does not ensure a profit or protect against a loss.

Contact us today to start a conversation

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A Complete Guide to Family Governance: What It Is and Why Your Family Needs It

father and son hike to a beautiful overlook in the fall

Strong families often share values and a long-term vision. But as wealth grows and generations multiply, even close families can find themselves disagreeing over finances, roles, and direction. Family governance provides a framework for making decisions together, resolving disagreements, and protecting what you’ve built.

This guide explains how family governance helps preserve both family wealth and relationships across generations.

Key Takeaways

  • Family governance is a structured system of principles, roles, and processes that helps families make decisions, communicate, and plan for the future together.
  • Without intentional planning, family wealth is often difficult to sustain across multiple generations. Clear governance structures may improve the likelihood of a successful multi-generational wealth transfer.
  • Core components often include a family mission statement, family constitution, family council, and succession plan, tailored to your unique family values and needs.
  • The best time to start is before you need it. Waiting until conflict erupts makes governance harder to build and less effective.
  • A fiduciary advisor can provide objectivity and structure that families may struggle to create on their own.

What Is Family Governance?

Family governance is a set of principles, rules, and procedures that guide how a family makes decisions, communicates, and transitions wealth and leadership across generations.

Think of it as an operating framework for your family’s financial life, helping keep everyone informed, involved, and aligned.

Family governance differs from corporate governance in important ways. Corporate governance focuses on shareholders and regulatory obligations, while family governance centers on relationships, shared values, and long-term legacy.

It addresses questions that traditional financial planning alone cannot answer:

  • How do we prepare the next generation to manage wealth responsibly?
  • How do we resolve disagreements without damaging family relationships?
  • Who participates in decisions, and at what stage?

The IFC Family Business Governance Handbook describes governance as a bridge between a family’s emotional bonds and its financial responsibilities. When that bridge is strong, families are better positioned to navigate change across decades.

The Real Threat to Family Wealth 

Some of the most common challenges for families are often communication-related.

Breakdowns in trust, preparation, and shared expectations can undermine even substantial financial resources. Families that avoid discussing wealth often discover too late that younger generations have very different expectations or levels of financial literacy.

Effective family governance directly addresses these risks. It creates a shared understanding of the family’s wealth, its purpose, and each person’s role in stewarding it. It also builds a framework for conflict resolution before disagreements become personal. 

Perhaps most importantly, governance prepares the next generation. Families that actively educate their children about financial responsibility and decision-making are more likely to develop heirs who are ready to steward wealth thoughtfully, not just inherit. 

Key Components of a Family Governance Structure 

Every family’s governance looks different, but the most effective structures share several core elements.

Family Mission Statement

A family mission statement captures the family’s shared values and purpose. What do you want your wealth to accomplish? What principles should guide your decisions? Writing it down creates alignment and accountability.

Family Constitution or Charter

A family constitution or charter translates those values into practical rules. It defines how decisions are made, who has authority in various areas, and what happens during transitions. Think of it as your family’s rulebook.

Family Council

A family council serves as the governing body. This is a regular forum where family members discuss finances, review goals, address concerns, and make collective decisions. Effective councils meet on a set cadence, whether quarterly or semiannually, and follow an agenda to keep discussions productive.

Clear Roles

Clearly defined roles ensure everyone knows their responsibilities. For example: 

  • Who manages day-to-day finances? 
  • Who sits on the council? 
  • Who communicates with outside advisors? 

Role clarity reduces confusion and prevents power struggles.

Succession Plan

Succession planning is often one of the most important elements of governance. It outlines how leadership, decision-making authority, and financial stewardship transition from one generation to the next. 

Without a clear plan, generational transitions can become complicated and emotionally charged.

Conflict Resolution

Finally, every governance structure needs a conflict resolution mechanism. Disagreements are inevitable in any family. Having a pre-agreed process, whether mediation, a vote, or advisory input, keeps conflict from becoming destructive.

Building a Strong Family Governance Plan

Building governance is a process, not a one-time event. Here’s how families can approach it thoughtfully. 

  1. Start with shared values and vision. Before writing rules, have honest conversations about what your family cares about. Legacy, philanthropy, education, entrepreneurship; let your values shape the structure rather than the other way around.
  2. Involve all generations. Governance built by one generation and handed down to the next rarely sticks. Include younger family members in conversations early.
  3. Define roles clearly from the start. Ambiguity breeds resentment. Be specific about who does what, and revisit roles as circumstances change.
  4. Schedule regular family meetings. Governance only works if you practice it. Quarterly or semiannual family assemblies keep everyone connected, informed, and accountable.
  5. Educate the next generation. Don’t assume your children will absorb financial wisdom through observation. Create structured opportunities for next-generation education and preparation: mentorship, involvement in philanthropic decisions, or guided investment experiences.
  6. Work with a trusted advisor. An experienced fiduciary advisor brings objectivity, structure, and expertise that families often struggle to provide internally. They can facilitate difficult conversations, identify gaps in your plan, and keep the process on track.

Build flexibility into your plan. Families evolve. Marriages, births, deaths, career changes, and market shifts all affect governance. Design your structure to adapt without losing its foundation. 

When Should You Start? 

Several milestones often signal that it may be time to formalize family governance:

  • Multiple generations are involved in wealth decisions or family enterprises
  • A significant wealth event has occurred, such as the sale of a business, a large inheritance, or a liquidity event
  • Family business transitions are on the horizon, including retirement or leadership changes
  • Growing complexity in your financial picture, whether through new investments, philanthropic commitments, or expanding family branches

If any of these situations apply, beginning the governance conversation sooner rather than later can be beneficial.

You do not need a perfect plan immediately. What matters most is establishing a starting point and committing to building the framework together.

How a Trusted Advisor Can Help 

Family dynamics can make objective decision-making difficult. Parents who built the wealth may find it challenging to share control. Siblings may avoid difficult conversations to preserve harmony. Younger family members may feel their perspectives are overlooked.

A fiduciary advisor serves as a neutral facilitator, guiding your family through the process with professionalism and care. Advisors who work with multigenerational families have often seen both successful governance models and common pitfalls.

At SKY Investment Group, our approach to working with families is holistic. We don’t just manage portfolios. We help families build the structures that support their wealth, their relationships, and their legacy. From facilitating your first family meeting to refining your governance plan over time, we’re a partner in the process.

Frequently Asked Questions

Can family governance work if some family members aren’t interested in participating?

Yes, although it may take time. Many families begin with those who are willing to engage and build a structure that allows others to participate later. As governance begins producing tangible benefits—such as clearer communication or expectations—participation often grows.

How formal does a family governance plan need to be?

The appropriate level of formality depends on the size and complexity of the family.

A small family may only need a written mission statement and periodic meetings, while a multigenerational family with businesses, trusts, and philanthropic structures may benefit from a formal constitution and council.

What happens if family governance conflicts with an existing trust or legal document?

Governance frameworks are typically advisory rather than legally binding. They are designed to complement legal structures, such as trusts and estate plans, rather than replace them. 

If a conflict arises, the legal document governs. That said, ideally governance planning aligns family intentions with the existing legal framework.

Should in-laws or spouses participate?

This is one of the most sensitive questions in family governance. Some families include spouses in meetings and educational programs but limit formal voting or decision-making roles to blood relatives or designated members. There is no universal answer, but clarity and consistency in the policy are important.

SKY Investment Group, LLC is an SEC registered investment advisor. Being registered with the SEC does not imply any specific level of skill or training.

Neither SKY Investment Group, LLC nor Aspen provide tax or legal advice—please contact a professional for advice in such matters.

Investing involves the risk of loss, including the risk of loss of the entire investment. Diversification does not ensure a profit or protect against a loss.

Contact us today to start a conversation

multigenerational family

Understanding Connecticut and Federal Estate & Inheritance Taxes in 2026

Understanding Connecticut and Federal Estate & Inheritance Taxes in 2026

Many Connecticut families aren’t sure how “death taxes” work, whether inheritance taxes still exist, or what steps they can take to protect the wealth they’ve worked hard to build. This guide breaks the policies down simply so you can better understand your options and make informed decisions for your family’s future.

Key Takeaways

  • Connecticut imposes a state estate tax, but no longer imposes an inheritance tax.
  • As of 2026, Connecticut is the only state with a state-level gift tax.
  • Wealth-transfer strategies can significantly reduce or eliminate unexpected tax burdens.
  • Early planning helps protect your legacy and ensures assets pass efficiently to the people you care about most.

Estate Taxes vs. Inheritance Taxes: What’s the Difference?

Although often used interchangeably, these terms refer to very different systems.

Estate tax is charged on the value of the estate itself before anything is distributed to beneficiaries. The estate pays the tax.

Inheritance tax is charged on the person receiving an inheritance, and the rate can vary based on their relationship to the deceased.

Connecticut previously had an inheritance tax which was referred to as the succession tax, but today only the estate tax remains. Working with a qualified advisor can help you take advantage of current rules and protect more of what you’ve built for your heirs.

Learn more about taxes in Connecticut.

See how SKY can help navigate your specific situation.
Talk to An Advisor

The Connecticut Estate Tax

Connecticut’s estate tax has distinct thresholds and mechanics that are worth understanding before planning decisions are made.

Exemption Amount

Connecticut’s estate tax exemption mirrors the federal exemption in 2026: $15 million per person.

For married couples, the exemption can total $30 million with proper estate planning, often using trusts. Connecticut currently does not have a portability election that would permit a surviving spouse to claim a deceased spouse’s unused exemption.

Tax Rate Structure

Connecticut’s estate tax is straightforward:

  • A flat 12% tax rate applies only to the portion of the estate above the exemption, after taking into account deductible expenses and the unlimited marital and charitable deductions.
  • There is a tax cap of $15 million, meaning the total tax bill (including gift taxes) can never exceed roughly $15 million.

What Property Is Subject to Connecticut Estate Tax?

1. Connecticut Residents: What’s Included

  • Worldwide real estate
  • Investments, bank accounts, brokerage assets
  • Business interests (LLCs, partnerships, corporations)
  • Personal property (vehicles, jewelry, collectibles, etc.)
  • Retirement accounts and certain life insurance proceeds

Note, however, CT resident estates get a credit for real or tangible personal property located outside of CT. 

2. Non-Residents: What Connecticut Does and Does Not Tax

For non-residents, Connecticut taxes only real estate and tangible personal property located in Connecticut. The tax is calculated using an apportionment formula that applies the estate tax only to the portion of the estate attributable to Connecticut-situs property.

Generally Taxable for Non-Residents

  • Connecticut real estate (homes, rentals, vacation property)
  • Tangible personal property physically located in Connecticut
  • Certain business assets tied to a Connecticut location or operation

Generally Not Taxable for Non-Residents

  • Stocks, bonds, mutual funds
  • Bank and brokerage accounts
  • Life insurance
  • Intangible business interests that don’t own Connecticut real or tangible personal property (most LLC or corporate membership interests)

In short, Connecticut subjects residents to estate tax on all assets except for real or tangible personal property located outside of CT, and taxes non-residents on Connecticut-based real or tangible personal property.

The Connecticut Gift Tax

In addition to the estate tax that applies at death, Connecticut has a gift tax on certain lifetime transfers, and both share the same overall exemption. The only state with its own gift tax, Connecticut uses a unified estate-and-gift system where lifetime giving directly reduces the exemption available at death.

Unified Estate & Gift System

Connecticut is one of the few states with its own gift tax. Like the estate tax, it has:

  • A lifetime gift exemption equal to the estate tax exemption.
  • A 12% tax on all lifetime gifts exceeding that total exemption.

What Counts as a CT Taxable Gift

The following are typically considered gifts for CT gift tax purposes:

  • Gifts made by Connecticut residents of any property, except for gifts of real estate and tangible personal property located outside of Connecticut.
  • Gifts made by non-residents of Connecticut-sited real and tangible personal property.

However, certain payments are not considered taxable gifts, including:

  • Payments made directly to medical providers.
  • Tuition paid directly to educational institutions.
  • Gifts that do not exceed the annual federal gift tax exclusion amount, so long as the gifts qualify for annual exclusion treatment.

It is important to properly report and keep track of Connecticut lifetime gifts to avoid unexpected estate tax consequences later.

How Lifetime Gifting Impacts Your Estate

Any taxable gifts you make during life reduce the exemption available at death, directly affecting your estate’s tax exposure. Gifting earlier can be advantageous: once assets are transferred, all future growth occurs outside your estate, lowering taxable exposure and letting assets compound for beneficiaries, especially fast-growing investments, real estate, or business interests.

Federal Estate & Gift Tax

Because Connecticut’s tax system interacts with the federal system, it’s important to understand the federal rules as well.

Beginning in 2026, new federal legislation sets the exemption at $15 million per individual (indexed for inflation going forward), rather than allowing it to drop by half as previously scheduled.

Federal Estate Tax Rates

If the estate exceeds the federal estate tax exemption, the excess is taxed at a flat rate of 40%.

Unified Federal Gift & Estate System

The federal government uses a combined exemption for lifetime gifts and estate transfers.

Key components include:

  • Tracking cumulative lifetime gifts.
  • Annual exclusion gifts (e.g., $19,000 per recipient in 2026).
  • Coordinating federal and Connecticut planning to avoid unnecessary overlap or exposure.

Common Wealth-Transfer Strategies to Reduce Taxes

Thoughtful planning can ease the tax burden and protect your legacy.

1. Annual Exclusion Gifts

Regular, smaller gifts can gradually transfer wealth without reducing your lifetime exemption. This strategy is simple, predictable, and effective over time.

2. Irrevocable Trusts

Tools like:

  • Irrevocable Life Insurance Trusts (ILITs)
  • Spousal Lifetime Access Trusts (SLATs)
  • Grantor Retained Annuity Trusts (GRATs)
  • Generation-Skipping or Dynasty Trusts

By making gifts to irrevocable trusts, you can remove assets from your estate while still supporting your family or charitable goals.

3. Business & Real Estate Planning

Owners of closely held businesses or real estate may be able to use strategic planning tools like Family Limited Partnerships, valuation discounts, and gifting minority interests to transfer ownership more efficiently. These approaches help reduce the taxable value of transfers while allowing families to pass control and long-term value in a tax-aware way.

4. Charitable Planning

If philanthropy is part of your vision, these options can lower taxes while benefiting causes you care about.

  • Charitable Remainder Trusts (CRTs): Provide you or your beneficiaries with income for a set period, with the remaining assets going to charity. Provides a charitable income tax deduction and reduces your taxable estate.
  • Charitable Lead Trusts (CLTs): Give income to a charity first for a defined term, after which the remaining assets can pass to your heirs with potential tax benefits.
  • Direct Gifts to Charity: Simple donations made during your lifetime that immediately support charitable causes and can reduce your taxable estate.

5. Relocation / Change of Residency

Many retirees or high-net-worth individuals choose to move to states with no estate or inheritance tax, like Florida, Nevada, or Texas. To be recognized, a change in domicile must be supported by actions, documentation, and intent. Clients should consult with SKY and their tax and estate counsel to document and ensure the abandonment of Connecticut residence.

6. Life Insurance for Liquidity

Federal estate taxes are due within nine months of death, but in Connecticut, they are due six months after death. For those who have potential estate tax exposure, life insurance, especially when held in an ILIT, can be a possible source of  liquidity to pay estate taxes without selling important assets under pressure.

Important Administrative Considerations

A strong estate plan also depends on proper maintenance:

  • Keep beneficiary designations up to date across retirement accounts, bank accounts, and insurance.
  • Understand filing requirements:
    • CT Form CT-706/709 for estate and gift tax or CT Form CT-706 NT (for nontaxable estates)
    • Form 706 for federal estate tax
    • Form 709 for federal gift tax
  • File timely to elect federal portability for federal estate tax purposes (not available in Connecticut).
  • Remember the 9-month federal deadline for paying estate tax, and the 6-month deadline for Connecticut.

These technical steps can make the difference between a smooth settlement and unexpected tax consequences.

Your Connecticut Tax Planning Strategy

Connecticut’s estate and gift tax system adds complexity to planning, but with the right guidance, families can reduce unnecessary taxes, protect their wealth, and pass assets more efficiently to the next generation.

At Sky IG, we’re dedicated to helping Connecticut families understand their options, make tax-informed decisions, andeducate the next generation about responsible financial planning. Whether you’re starting to think about long-term planning or navigating a current estate, we’re here to help you make the most of your situation.

Contact us to start the conversation.

This article is for informational purposes only and is not meant to constitute tax, legal or financial advice. SKY Investment Group LLC (“SKY”) is an SEC registered investment advisor. Being registered with the SEC does not imply any specific level of skill or training. SKY is neither a certified public accounting firm nor a law firm and does not provide tax or legal advice, respectively, to clients; such services are provided through select third parties unaffiliated with SKY. Tax and estate planning strategies are unique to each client’s circumstances and success cannot be guaranteed. Please contact a tax or legal professional for advice in such matters. Investing involves the risk of loss, including the risk of loss of the entire investment. Diversification does not ensure a profit or protect against a loss.

Contact us today to start a conversation

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How Are Capital Gains Taxed In Connecticut (CT)?

How Are Capital Gains Taxed In Connecticut (CT)?

THE COMPLETE GUIDE TO CONNECTICUT CAPITAL GAINS AND TAX RATES

Capital gains can have a meaningful impact on your tax picture in Connecticut, yet many taxpayers are unclear on how gains are treated at the state level, how a sale may affect their overall tax rate, or how Connecticut rules differ from federal law.

This guide explains how capital gains are taxed in Connecticut, how they flow through the state’s income tax system, how federal and state rules interact, and what to consider when planning significant financial transactions.

As a Connecticut-based financial advisory firm, our goal is to provide clarity as you make informed tax and investment decisions.

Learn more about taxes in Connecticut.

See how SKY can help navigate your specific situation.
Talk to An Advisor

Key Takeaways

  • Connecticut taxes capital gains as ordinary income.
  • There is no reduced CT long-term capital gains rate.
  • Large gains can push income into higher state brackets.
  • Most sales trigger both federal and Connecticut tax.

What Is Capital Gain?

A capital gain is the profit you realize when you sell an asset for more than its purchase price. These items, known as capital assets, can include many types of property and investments.

Capital assets include:

  • Stocks and Bonds
  • ETF’s and Mutual Funds
  • Private Equity and Venture Capital Investments
  • Real Estate
  • Business Ownership Interests
  • Collectibles
  • Other Personal Investments

When a gain occurs, it increases your taxable income. That income becomes part of both your federal income tax calculation and your Connecticut state income tax calculation.

There are two primary types of capital gains:

  • Short-Term Capital Gains: Assets held for one year or less
  • Long-Term Capital Gains: Assets held for more than one year

At the federal level, this distinction matters because long-term capital gains are often taxed at preferential rates, while short-term gains are taxed as ordinary income.

For state tax purposes, both short-term and long-term capital gains are included in Connecticut taxable income and taxed at the same progressive state income tax rates.

How Connecticut Taxes Capital Gain Income

Connecticut Does Not Have A Separate Capital Gains Tax Rate

Connecticut does not impose a separate state capital gains tax. Instead, Connecticut treats capital gains income the same way it treats wages, interest, dividends, or other income. The gain becomes part of your Connecticut adjusted gross income, and the state’s progressive income tax system applies.

When you earn a capital gain, that gain:

  • Increases taxable income
  • Moves you through Connecticut state tax brackets
  • Raises total Connecticut state income tax liability based on your bracket

Connecticut State Income Tax Rates And Capital Gains

Connecticut uses a progressive income tax system, meaning your tax rate increases as your income increases. As capital gains increase your total income, they can push more of your income into a higher tax bracket.

Connecticut Income Tax Brackets (Applied To Capital Gains As Regular Income)

Connecticut Taxable Income (Single Filer)
Connecticut Taxable Income (Married, Filing Jointly)
Connecticut Tax Rate
$0 – $10,000
$0–$20,000
2.00%
$10,000 – $50,000
$20,001–$100,000
4.50%
$50,000 – $100,000
$100,001–$200,000
5.50%
$100,000 – $200,000
$200,001–$400,000
6.00%
$200,000 – $250,000
$400,001–$500,000
6.50%
$250,000 – $500,000
$500,001–$1,000,000
6.90%
$500,000+
$1,000,000+
6.99%

Because capital gains are included in Connecticut taxable income, they can materially affect your state tax bill during major financial events, such as when you:

  • Sell a home with taxable gain
  • Sell appreciated securities
  • Sell business ownership
  • Liquidate a large investment

As a result, a capital gain is typically subject to federal capital gains tax and Connecticut state income tax at the same time.

Example: How A Capital Gain Can Affect Connecticut Taxes

Assume a Connecticut resident, single filer, earns $180,000 of regular income and sells appreciated stock for a $150,000 long-term capital gain.

At the federal level, the gain is taxed at long-term capital gains rates, potentially plus the net investment income tax, depending on total income.

At the Connecticut level, the same $150,000 gain is added to state taxable income, increasing total Connecticut income to $330,000 and pushing portions of the gain into higher state brackets including the 6.5% and 6.9% rates that would not have applied without the sale. The result is a layered tax outcome: preferential federal capital gains tax treatment combined with higher-rate taxation at the state level. This interaction often surprises taxpayers and materially increases the overall tax cost of a large sale.

Simple Example Of How A Capital Gain Moves Through CT Tax Brackets

Portion Of Gain Taxed
Connecticut Rate
Tax Owed On Portion
First $10,000
2.00%
$200
Next $40,000
4.50%
$1,800
Next $50,000
5.50%
$2,750
Next $100,000
6.00%
$6,000
Next $50,000
6.50%
$3,250
Remaining Amount
6.90% – 6.99%
Varies

This shows that not all of the gain is taxed at one single rate. Instead, pieces of the gain move through each tax bracket.

Reporting Capital Gains On A Connecticut Tax Return

Capital gains are reported on your Connecticut return through your federal income calculations. When a gain occurs, it increases your federal adjusted gross income, which then flows directly into your Connecticut adjusted gross income. As a result, the gain increases your Connecticut taxable income and may push a portion of it into higher state tax brackets.

Connecticut does not require a separate capital gains tax form. The state largely relies on your federal adjusted gross income and then applies Connecticut-specific rules and tax rates to determine your final tax liability.

 

Planning Considerations To Reduce Capital Gains Tax Impact

Connecticut’s tax treatment of capital gains is fixed, but when and how a gain is realized can materially affect the amount of tax owed and the timing of that liability. The following strategies do not eliminate capital gains tax, but they can help manage its impact.

Timing of sales

Spreading sales across multiple tax years or deferring a transaction may keep income from spilling into higher state tax brackets. This is especially relevant for business sales, large portfolio liquidations, or concentrated positions.

Using losses to offset gains

Capital losses from other investments can offset capital gains, reducing the amount of gain included in taxable income. Loss harvesting must follow IRS rules, including wash sale restrictions, but can be an effective tool when rebalancing portfolios.

Coordinating with retirement planning strategies

Large capital gains can affect income-based thresholds tied to retirement planning, such as Medicare premiums or the taxation of Social Security benefits. Coordinating asset sales with retirement income sources can help avoid unintended consequences.

Primary residence exclusion

Federal tax law allows eligible homeowners to exclude a portion of gain from the sale of a primary residence if ownership and use requirements are met. While Connecticut follows federal income definitions, understanding how this exclusion applies can significantly reduce the taxable gain reported at both the federal and state level.

Talk to an advisor about your unique tax situation.

Hear more about our personalized approach to tax mitigation.
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Support When You Need Guidance

Capital gains planning sits at the intersection of state and federal tax systems. Missteps can be costly, and significant gains often have lasting implications for cash flow, investment strategy, and long-term planning.

If you need thoughtful advice on how Connecticut’s capital gains tax aligns with your financial objectives, SKY IG can help you design a strategy that works for your unique situation.

 

Frequently Asked Questions

Does Connecticut conform to federal exclusions?
Generally, yes. Connecticut starts with federal adjusted gross income, so federal exclusions, such as the primary residence exclusion, typically flow through to the Connecticut return unless the state requires a specific adjustment.

Can capital losses reduce Connecticut taxes?
Yes. Capital losses that are allowed at the federal level also reduce Connecticut taxable income, subject to the same federal limitations on how losses may be used or carried forward.

Are seniors exempt from capital gains tax in CT?
No. Connecticut does not provide a senior-specific exemption from capital gains tax. Gains are taxed as part of ordinary income regardless of age. However, there is a specific, limited exception for home sales by older residents under state law: if a taxpayer is age 65 or older and has owned and used their principal residence for at least five of the previous eight years, the gain from that sale may be exempt from Connecticut capital gains tax.

This article is for informational purposes only and is not meant to constitute tax, legal or financial advice. SKY Investment Group LLC (“SKY”) is an SEC registered investment advisor. Being registered with the SEC does not imply any specific level of skill or training. SKY is neither a certified public accounting firm nor a law firm and does not provide tax or legal advice, respectively, to clients; such services are provided through select third parties unaffiliated with SKY. Tax and estate planning strategies are unique to each client’s circumstances and success cannot be guaranteed. Please contact a tax or legal professional for advice in such matters. Investing involves the risk of loss, including the risk of loss of the entire investment. Diversification does not ensure a profit or protect against a loss.

Contact us today to start a conversation

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Connecticut 529 College Savings: How to Choose the Right Plan for Your Family

Bustling university campus scene, diverse students walking between buildings, lush green spaces, architectural mix of classic and modern structures

Saving for a child’s future education is one of the most meaningful steps a family can take, but it can also feel overwhelming. Connecticut parents often hear about CHET, national 529 plans, tax benefits, and withdrawal rules, without clear guidance on how they actually compare.

This guide explains how 529 plans work, what CHET offers, and when a Connecticut plan makes sense versus choosing a national option. We focus on the practical factors that matter most (tax treatment, investment flexibility, fees, and long-term use) so you can choose a plan that aligns with your family’s goals and avoid costly missteps. SKY Investment Group helps families and individuals plan for the cost of higher education. Our goal is to offer clarity that helps you make confident decisions for your family.

Understanding 529 College Savings Plans

A 529 plan is a tax-advantaged savings program that helps families prepare for future education expenses. Contributions grow tax-free, and withdrawals used for qualified higher education expenses avoid federal tax.

Families choose 529 college savings plans because they offer:

  • Tax-free growth when used for qualified expenses
  • A dedicated account for education goals
  • The ability to use funds at accredited colleges, universities, and many trade or vocational programs
  • Limited use of funds for K–12 tuition
  • Limited use of funds for student loan repayments

A 529 account can be opened by anyone, with contributions from parents, grandparents, other relatives, or friends who want to support a child’s education savings. Savings may come from multiple 529 accounts, and families may coordinate withdrawals from different accounts when paying future college costs.

Withdrawals used for non-qualified expenses may be subject to federal income tax and a federal tax penalty. A financial advisor can help families coordinate contributions, manage investment choices, and stay aligned with tax rules to make the most of their education savings.

Which 529 plan is right for you?

Talk to an advisor to learn about your options.
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Why Connecticut Families Often Start With CHET

Connecticut residents often begin their search with the Connecticut Higher Education Trust 529 college savings program, known as CHET. This plan is sponsored by the State of Connecticut and offers a clear structure for families who want to save for higher education.

Key features include:

  • A Connecticut state income tax deduction for contributions
  • A range of portfolios designed for long-term saving
  • A simple online enrollment process
  • Tools that help families track progress toward college goals

For many local families, the state income tax deduction becomes an important part of their decision. This deduction is not available for plans sponsored by other states.

How CHET Works

The Connecticut 529 plan gives families a dedicated way to save for future education expenses. CHET supports both residents and nonresidents, although the state income tax deduction applies only to Connecticut taxpayers.

Investment Options With a Clear Structure

CHET includes several portfolio types that suit different saving styles:

  • Age-based portfolios that shift over time
  • Static portfolios with steady risk exposure
  • Individual fund portfolios for families who want specific allocations

These options allow families to match investment objectives to the child’s age and the planned timeline for future education costs.

Tax Advantages for Connecticut Residents

Connecticut residents may deduct CHET contributions on a per-beneficiary basis. This can reduce state income tax and help families direct more resources toward future education savings. Tax benefits vary by household and should be reviewed with a tax professional.

Flexible Use of Funds

CHET funds may be used to pay for:

  • Tuition at accredited colleges and universities
  • Room and board
  • Textbooks and course materials
  • Required equipment or supplies
  • Certain apprenticeship program expenses
  • A limited amount of K–12 tuition
  • Qualified education loan repayments within federal limits

Oversight From the State of Connecticut

CHET operates under the authority of the Office of the Treasurer. The plan follows state and federal rules that guide investment choices, disclosure requirements, and use of funds.

Comparing CHET With Other 529 College Savings Plans

CHET is Connecticut’s home-state 529 plan, but many families also review plans from other states. National programs can differ in fees, investment options, portfolio structure, and flexibility, which may make another plan appealing depending on your goals.

Families often compare plans because they may:

  • Prefer different investment styles or portfolio options
  • Want the option to open a plan outside their home state
  • Expect to move out of Connecticut
  • Care how age-based portfolios are structured
  • Want to evaluate fee differences and long-term impact

For Connecticut residents, CHET offers a meaningful advantage: it is the only plan that provides a Connecticut state income tax deduction, which can significantly benefit long-term savings.

When CHET May Make Sense

  • You want Connecticut’s state income tax deduction
  • You prefer a clear and straightforward investment lineup
  • You plan to make steady, predictable contributions
  • You value a program sponsored by the State of Connecticut

When Another State’s 529 May Make Sense

  • You want investment choices CHET does not offer
  • You expect to relocate before a child begins college
  • You want flexibility to compare multiple plan structures
  • The Connecticut state deduction is not the deciding factor

How the Connecticut State Tax Deduction Works

CHET’s deduction applies on a per-beneficiary basis each year.

A few important points:

  • The deduction applies only to CHET.
  • Funds deducted must remain in the plan for the taxable years following the deduction.
  • Withdrawals used for qualified expenses remain tax-free at the federal level.
  • Withdrawals used for non-qualified purposes may be subject to federal income tax and a federal tax penalty.

Families who want to maximize state benefits generally stay with CHET for this reason.

How to Open a CHET 529 College Savings Account

Parents and caregivers can open a CHET account through the official CHET website. The process is simple:

  1. Create or sign in to an online account.
  2. Provide information about the beneficiary.
  3. Select investment options that match your goals.
  4. Make an initial contribution.
  5. Set up ongoing contributions if desired.

After setup, the account can be managed and updated as your child’s education plans take shape.

How 529 Plans Fit Into a Broader Financial Plan

A 529 plan works best when it’s part of a larger financial picture, not a standalone decision. For many families, the challenge isn’t choosing whether to save for education, but how to balance that goal alongside other priorities.

Balancing education savings and retirement
College is important, but retirement can’t be financed later. Many families prioritize retirement contributions first, then direct additional savings toward a 529 plan to avoid compromising long-term security.

Considering financial aid implications
529 plans are generally treated favorably in financial aid formulas, but account ownership matters. Parent- and grandparent-owned accounts are assessed differently, and understanding how assets and distributions are counted can help avoid unintended reductions in aid.

Coordinating with trusts, gifts, and estate planning
For higher-net-worth families, 529 plans often fit into broader wealth-transfer strategies. Contributions can align with annual gifting, trust structures, and long-term estate planning when coordinated thoughtfully.

The role of grandparents and family gifting
529 plans offer grandparents a structured way to support education while retaining flexibility. Ownership, timing, and coordination with the family’s overall plan all influence how effective these contributions are.

A Path Forward for Connecticut Families

Choosing a 529 plan comes down to your family’s timeline, tax situation, and comfort with long-term investing. For many Connecticut families, CHET offers a straightforward way to save for education while capturing state tax benefits, but the right choice depends on your broader financial picture.

SKY Investment Group helps families compare 529 options, understand how education savings fit into their overall plan, and make informed decisions with confidence. If you’d like guidance building or refining a college savings strategy, our team is here to help.

This article is for informational purposes only and is not meant to constitute tax, legal or financial advice. SKY Investment Group LLC (“SKY”) is an SEC registered investment advisor. Being registered with the SEC does not imply any specific level of skill or training. SKY is neither a certified public accounting firm nor a law firm and does not provide tax or legal advice, respectively, to clients; such services are provided through select third parties unaffiliated with SKY. Tax and estate planning strategies are unique to each client’s circumstances and success cannot be guaranteed. Please contact a tax or legal professional for advice in such matters. Investing involves the risk of loss, including the risk of loss of the entire investment. Diversification does not ensure a profit or protect against a loss.

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