Capital Gains Tax Planning for High-Net-Worth Investors in 2026

The short answer: for 2026, a high-income investor generally pays 20% federal tax on long-term capital gains, plus the 3.8% net investment income tax, for a combined 23.8%. Gains on assets held a year or less are taxed as ordinary income, which can reach 37% plus the same 3.8%. Oklahoma taxes the gain separately, but it offers a deduction for certain Oklahoma property. The good news is that when and how you sell is often within your control, and that is where planning pays.

Below, we walk through the 2026 rates, Oklahoma’s rules, and the main tools investors use to keep more of a gain.

Short-term vs. long-term: the one-year line

The IRS treats a gain as long-term if you held the asset more than one year. The count starts the day after you bought it and includes the day you sell. Anything held one year or less is short-term.

• Short-term gains are taxed as ordinary income, at the same rates as wages or business income. For 2026, the top 37% rate begins above $768,700 of taxable income for married couples filing jointly and above $640,600 for single filers.
• Long-term gains get lower rates of 0%, 15%, or 20%, depending on your taxable income.

A few types of long-term gain have their own maximum rates: up to 25% for the part of a real estate gain that comes from past depreciation (unrecaptured Section 1250 gain), and up to 28% for collectibles such as art and coins.

The 2026 long-term capital gains brackets

These thresholds come from the IRS’s 2026 inflation adjustments and apply to taxable income, including the gain itself.

Most of our readers with a large gain will land in the 20% bracket for at least part of it. That makes the 3.8% tax the next piece to understand.

The 3.8% net investment income tax

The net investment income tax (NIIT) adds 3.8% on investment income, including capital gains, interest, dividends, and passive rental income. It applies to the smaller of your net investment income or the amount your modified adjusted gross income exceeds $250,000 (married filing jointly), $200,000 (single or head of household), or $125,000 (married filing separately). The IRS notes these thresholds are not indexed for inflation, so more investors cross them every year.

Not every gain is investment income. Gain on selling an interest in a partnership or S corporation counts only to the extent you were a passive owner, so an owner who works in the business may avoid the 3.8% on that sale. Our guide to the net investment income tax covers how to keep it where it belongs.

How Oklahoma taxes capital gains

Oklahoma doesn’t have a separate, lower rate for capital gains. A gain included in your federal adjusted gross income is generally part of your Oklahoma taxable income, figured on your Oklahoma return separately from your federal tax.

The exception is the Oklahoma capital gain deduction (68 O.S. § 2358, claimed on Form 561). Residents can deduct qualifying net capital gain from:

• Real or tangible personal property located in Oklahoma and owned for at least five uninterrupted years before the sale.
• Stock or an ownership interest in an Oklahoma company, LLC, or partnership owned for at least two uninterrupted years.
• Oklahoma assets sold as part of selling all or substantially all of an Oklahoma business, where the assets were owned at least two uninterrupted years.

An “Oklahoma company” here means one whose primary headquarters has been in Oklahoma for at least three uninterrupted years before the sale. Stock in companies headquartered elsewhere doesn’t qualify. Installment payments can qualify if the holding period was met on the date of sale. If the gain comes through a partnership or S corporation that made the Oklahoma pass-through entity election, the deduction for that gain is figured at the business level on Form 561-PTE instead, which keeps the business tax and your personal tax separate.

Planning tools that lower or delay the tax

1. Time the sale

Holding a few more weeks to cross the one-year mark can move a gain from ordinary rates to long-term rates. Spreading large sales across two tax years, or selling in a year when your other income is lower, can keep more of the gain in the 15% bracket or under the NIIT threshold.

For example, take a hypothetical married couple whose taxable income is already above $768,700. Another $100,000 of short-term gain would cost about $40,800 of federal tax (37% plus 3.8%). The same gain held past one year would cost about $23,800 (20% plus 3.8%), a difference of $17,000.

2. Harvest losses

Selling investments that are down in value creates capital losses that offset gains. If losses exceed gains, up to $3,000 a year ($1,500 married filing separately) can offset other income, and the rest carries forward. Watch the wash sale rule: if you buy substantially identical stock within 30 days before or after the loss sale, including in your IRA or through your spouse, the loss is disallowed for now.

3. Give appreciated stock instead of cash

If you give to charity, donating shares held more than a year usually lets you deduct their market value without ever paying tax on the growth. See donating appreciated stock for how it works.

4. Plan around the step-up in basis

Property you inherit generally takes a basis equal to its fair market value at the owner’s death, so the growth during the owner’s life is never taxed. Property you receive as a gift keeps the giver’s basis. For older investors with large unrealized gains, deciding what to sell, what to give, and what to hold can matter as much as the rate.

5. Use a 1031 exchange for real estate

Since 2018, like-kind exchanges apply only to real property held for business or investment. Rolling the sale proceeds into replacement property defers the gain, but the deadlines are strict: identify the replacement within 45 days and receive it within 180 days (or by your return due date, if earlier). Our 1031 exchange guide walks through the steps.

6. Consider an Opportunity Fund

Investing a gain in a Qualified Opportunity Fund, generally within 180 days, can defer the tax, and holding the fund investment at least 10 years can make its appreciation free of federal tax. Gains deferred under the original rules must be recognized by December 31, 2026. The 2025 tax law made the program permanent, with a new round of zones starting January 1, 2027.

7. Spread a sale with an installment note

When you sell a business or property and receive payments over time, the installment method generally lets you report the gain as you collect it. This can keep each year’s gain in a lower bracket. It doesn’t work for publicly traded stock or inventory, and any depreciation recapture is taxed in the year of sale no matter when you’re paid.

How we help

At Cannon & Brown Tax Advisors, we model a sale before it happens: federal and Oklahoma tax shown separately, with timing and strategy options tested against your real numbers and reviewed by your tax strategist. If you’re weighing a large sale, start with a free tax analysis.

Illustrative example. The people and figures in this article are hypothetical, used to explain how the rules work. They are not a client and not a promise of results.

This article is educational and is not tax advice for your situation. Tax law may change, which may change these rules and numbers.

Sources

• IRS: Revenue Procedure 2025-32 (2026 inflation adjustments)
• IRS: Topic no. 409, Capital gains and losses
• IRS: Net investment income tax
• IRS: Questions and answers on the net investment income tax
• Oklahoma Tax Commission: Form 561, Oklahoma Capital Gain Deduction
• IRS: Publication 550, Investment Income and Expenses (wash sales)
• IRS: Publication 551, Basis of Assets
• IRS: Like-kind exchanges, real estate tax tips
• IRS: Instructions for Form 8824
• IRS: Opportunity zones frequently asked questions
• U.S. Treasury: Qualified Opportunity Zones
• IRS: Topic no. 705, Installment sales