For investors with significant capital gains
Sold appreciated stock this year? Don't overpay the IRS.
If you're facing a large capital-gains tax bill from selling stock, RSUs, or a concentrated position, there may be legal strategies to defer, reduce, or even eliminate the tax. Get a free, no-obligation strategy review with a licensed specialist.
- 20+ years advising & $900M+ in transactions
- Series 7, 63 & 65 licensed — verifiable on FINRA BrokerCheck
- Strategies tailored to you, coordinated with your CPA & attorney
Request your free strategy review
Takes about 60 seconds. No cost, no obligation.
Reviewed for general accuracy by a licensed investment advisor. This article is educational and is not tax, legal, or investment advice — always consult your own CPA and attorney.
Key takeaways
- Selling appreciated stock can trigger federal capital gains tax of up to 20%, plus the 3.8% Net Investment Income Tax and state income tax — potentially 30%+ combined.
- A 1031 exchange cannot defer tax on a stock sale — it applies only to like-kind real property.
- Stock-sale gains can still be deferred or reduced through a Deferred Sales Trust (IRC §453), a Charitable Remainder Trust, or a Qualified Opportunity Zone fund, among others.
- Timing is critical: several strategies must be set up before the sale closes or before year-end, and Opportunity Zone reinvestment must occur within 180 days.
A stock sale can trigger a tax bill of 30% or more
When you sell long-held stock, the gain can be taxed at up to 20% in federal long-term capital gains, plus the 3.8% Net Investment Income Tax, plus state income tax — as high as 13.3% in California. Short-term gains, on assets held less than a year, are taxed as ordinary income and can be higher still.
On a $1,000,000 gain, $300,000+ can go to taxes.
That's money you may be able to keep working for you instead — if you plan before the deadlines pass.
The tax code offers legal ways to keep more of your gain
Most investors — and even many CPAs, who are focused on filing your return rather than proactive planning — never explore the deferral strategies available before and shortly after a sale. Depending on your situation, one or more of these may apply:
Deferred Sales Trust (IRC §453)
Sell into a trust and receive payments over time, so the gain is recognized — and taxed — gradually instead of all at once.
How the DST Plus™ strategy works →Charitable Remainder Trust (CRT)
Defer the gain, draw a lifetime income stream, claim a partial charitable deduction, and leave a legacy to the causes you care about.
Qualified Opportunity Zone Fund
Reinvest your gain within 180 days to defer it — with the potential to owe no tax on the new investment's growth after a 10-year hold.
Installment & structured sales
Spread recognition of the gain across multiple tax years to smooth your income and potentially stay in lower brackets.
Exchange funds & diversification
Hold a large concentrated position? Exchange into a diversified portfolio without triggering an immediate taxable sale.
1031 exchange (for real estate)
If part of your wealth is in investment property, a 1031 exchange into a DST can defer those gains too — a specialty of ours.
How a 1031 exchange works →Which strategy fits depends on your goals, timeline, and the type of asset. That's exactly what the strategy review is for.
Deferred Sales Trust vs. CRT vs. Opportunity Zone vs. 1031
Each strategy defers or reduces capital gains tax in a different way. Here's how the most common approaches compare at a glance:
| Feature | Deferred Sales Trust | Charitable Remainder Trust | Opportunity Zone Fund | 1031 Exchange |
|---|---|---|---|---|
| Works for a stock sale? | Yes | Yes | Yes | No — real property only |
| Tax treatment | Defers gain over installment payments | Defers + partial charitable deduction | Defers now; potential 0% on new growth after 10 yrs | Defers gain into replacement real estate |
| Access to income | Structured payments over time | Lifetime income stream | Illiquid until exit | Via replacement property cash flow |
| Key deadline | Before sale closes | Before sale closes | Within 180 days of sale | 45-day ID / 180-day close |
| Best suited for | Large gains, income flexibility | Charitably inclined investors | Long-horizon growth investors | Real estate owners |
A 1031 exchange is included for comparison only — it defers tax on real estate, not on a stock sale. Which strategy fits your situation depends on your goals, timeline, and assets.
Timing matters — some doors close at the sale, or at year-end
Several of these strategies must be structured before your sale closes or before December 31, and a Qualified Opportunity Zone reinvestment must happen within 180 days of the sale. The sooner you review your options, the more of them remain open to you.
How it works
Request your review
Tell us a bit about your situation using the short form. It takes about a minute.
We map your options
A licensed specialist reviews your gain, timeline, and goals, then outlines the strategies that actually fit.
You decide
Move forward only if it makes sense for you — in coordination with your own CPA and attorney. No pressure, no obligation.
Work with a specialist, not a salesperson
"Toni was great to work with and was more than happy to answer any and every question I had."
Jennifer C.
"Thanks Toni for helping me exchange my management-intensive rental property for a nice storage facility."
Bill F.
The bottom line
Selling appreciated stock can trigger a combined federal and state tax bill of 30% or more — but that outcome isn't automatic. Strategies such as a Deferred Sales Trust, a Charitable Remainder Trust, and a Qualified Opportunity Zone fund can defer, reduce, or in some cases eliminate the tax on your gain. A 1031 exchange won't help with a stock sale, but it remains a powerful tool for investment real estate. The right approach depends on your gain, your timeline, and your goals — and several strategies must be in place before your sale closes or before year-end. A free strategy review is the fastest way to see which options are still open to you.
Capital gains tax questions, answered
Can I do a 1031 exchange with stock?
No. A 1031 exchange applies only to like-kind real property — not stocks or securities. However, other strategies can defer or reduce capital gains tax on a stock sale, including a Deferred Sales Trust (IRC §453), a Charitable Remainder Trust, and a Qualified Opportunity Zone Fund.
How much tax will I owe when I sell appreciated stock?
Long-term gains (on assets held more than a year) are generally taxed at up to 20% federal, plus the 3.8% Net Investment Income Tax and any applicable state income tax — as high as 13.3% in California. Short-term gains are taxed as ordinary income. Your exact rate depends on your income and state of residence.
What strategies can defer capital gains tax on a stock sale?
Common approaches include a Deferred Sales Trust (IRC §453), a Charitable Remainder Trust, a Qualified Opportunity Zone Fund, installment or structured sales, and exchange funds for concentrated positions. Which one fits depends on your goals, timeline, and the type of asset — the purpose of the free strategy review is to identify it.
Is there a deadline to set these strategies up?
Often, yes. Several strategies must be structured before your sale closes or before December 31 of the year you sell, and a Qualified Opportunity Zone reinvestment must occur within 180 days of the sale. The sooner you review your options, the more of them remain available.
What does the strategy review cost?
Nothing. The initial strategy review is free and there is no obligation to move forward.
Do I need to be an accredited investor?
Some strategies are limited to accredited investors, but the strategy review itself is open to anyone exploring their options. We'll help you understand which approaches you qualify for.
For educational purposes only. This page is not tax, legal, or investment advice, and no specific outcome or tax savings is promised. Tax rules and deadlines are complex and subject to change, and results depend on your individual circumstances. Always consult your own CPA and attorney before implementing any strategy.