Sell Highly Appreciated Assets
Without Paying Capital Gains Tax
Turn Your Sale Into Lifetime Income and a Lasting Legacy
Selling a highly appreciated asset, like real estate, a stock portfolio, or a business often triggers a massive capital gains tax bill, reducing your proceeds by 20–30% or more.
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At Oakwood Summit, we help successful investors and business owners use a Charitable Remainder Trust (CRT) to sell appreciated assets tax-free, generate lifetime income, and create an enduring charitable legacy all in one coordinated strategy.
The Problem: A Tax Bill That Shrinks Your Hard-Earned Gain
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You’ve built or invested wisely, and now it’s time to harvest those gains. But the IRS has other plans.
When you sell:
Stocks trigger long-term capital gains taxes
Real estate can be hit with both capital gains and depreciation recapture
Selling your business often leads to one of the largest tax events of your life
For many owners, that means giving away hundreds of thousands or even millions in taxes before you can reinvest or retire
The Charitable Remainder Trust Solution
This strategy lets you eliminate capital gains tax at the time of sale, increase your cash flow, and maximize your charitable impact, all while maintaining financial security. A Charitable Remainder Trust (CRT) is an IRS-approved structure that allows you to:
1) Transfer your appreciated asset into the trust (before selling)
2) The trust sells the asset tax-free, because it’s a charitable entity
3) You receive annual income payments from the trust for life (or a set term)
4) The remainder—after your lifetime—goes to a charity of your choice
How It Works: Step-by-Step
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You contribute your appreciated asset—such as real estate, stock, or business interest—to the CRT.
The trust sells the asset with no capital gains tax owed at the time of sale.
The full sale proceeds remain inside the trust, where they can be reinvested for growth and income.
You receive annual income (typically 5–8%) for life or for a set number of years.
You receive a charitable deduction in the year you establish the trust.
Upon your passing, the remaining balance supports your chosen charities—leaving a lasting legacy.
Key Benefits
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Eliminate Capital Gains Tax on Sale
Sell appreciated assets without triggering capital gains—keeping 100% of your sale proceeds working for you.
Generate Lifetime Income
Receive a steady income stream, often higher than what the asset produced before the sale.
Immediate Charitable Deduction
Receive a tax deduction in the year you fund the trust, further reducing current taxes.
Diversify Without Tax Penalty
Reinvest the proceeds into diversified investments without losing value to taxes.
Leave a Meaningful Legacy
Support the causes or institutions you care about while maximizing your family’s financial security.
Example: Turning a Tax Bill Into Income and Impact
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A physician owns a medical practice valued at $3 million with a cost basis of $500,000.
If sold outright, the capital gains tax could exceed $600,000.By transferring the business interest into a Charitable Remainder Trust before the sale:
The practice is sold tax-free, preserving the full $3 million.
The owner receives $150,000–$200,000 annually for life.
They claim an immediate $400,000+ charitable deduction.
Upon passing, the remaining assets support a charitable foundation or cause they choose.
The result: No capital gains tax, lifetime income, and a lasting family legacy.
Who This Strategy Is For
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Business owners preparing to sell or retire
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Real estate investors with highly appreciated property
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Stockholders or executives with low-basis shares
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Families looking to reduce taxes and increase charitable impact
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Investors seeking tax-free diversification and lifetime income
Integrating a CRT With Your Overall Plan
At Oakwood Summit, we coordinate your Charitable Remainder Trust with your overall retirement, estate, and tax strategy. Our team works closely with your CPA, attorney, and advisors to:
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Structure and establish the CRT
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Coordinate the tax and legal documentation
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Optimize income and investment management inside the trust
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Align your charitable giving goals with your financial plan
Turn Taxes Into Lifetime Wealth and Legacy
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You don’t have to lose a third of your gains to taxes. With the right planning, you can sell tax-free, create predictable retirement income, and leave a legacy that lasts generations.
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Discover how a Charitable Remainder Trust can help you sell your business, real estate, or investments without capital gains taxes—and turn your success into lasting impact.