Sell it all this year, or spread the sale out?
Selling a large, appreciated position in one year can push part of the gain into the 20% capital-gain band and above the Net Investment Income Tax threshold. Selling equal parts over several years can keep more of it in lower bands, if the price holds while you wait.
Sell it all now, or over several years?
Compare federal tax on a long-term position sold in one year with selling equal parts over several years, using the 2026 capital-gain bands and Net Investment Income Tax.
The example, step by step.
The situation
- A $600,000 position with a $100,000 cost basis, all held more than a year
- Married filing jointly, with $200,000 of other taxable income each year
- Selling it all in 2026, or in equal parts over 5 years
What the calculator finds
- All at once: $413,700 of the $500,000 gain is taxed at 15% and $86,300 at 20%. That is $79,315 of capital-gains tax plus $18,324 of Net Investment Income Tax: $97,639, or 19.5% of the gain.
- Spread over 5 years: $100,000 of gain a year, all at 15%, plus $3,124 of NIIT. That is $18,124 a year and $90,618 in total.
- Spreading saves about $7,021 under these assumptions, with the price unchanged.
Spreading a sale can keep more of the gain in lower capital-gain bands. Waiting also keeps you exposed to one company, which can cost more than the tax saved.
What goes in.
What comes out.
Enter the position’s value and cost basis, confirm every share is long-term, then your filing status and other taxable income. The gain is stacked on top of that income in the 2026 long-term capital-gain bands of 0%, 15% and 20%.
The 3.8% Net Investment Income Tax applies to the part of the gain that lifts modified AGI above $200,000 for single filers or $250,000 for married couples filing jointly. Leave modified AGI blank to estimate it from taxable income plus the standard deduction.
For a spread sale, the gain is split into equal yearly parts and taxed the same way each year, at today’s brackets and price. You can add an optional flat state rate.
What it does not cover.
- The saving assumes the price stays the same while you wait. One company’s stock can fall far more than the tax difference.
- Gifting, charitable strategies, exchange funds, hedging, AMT and changes in your income or in tax law are not modeled.
- Short-term gains, wash sales, qualified small business stock and other special basis rules are outside its coverage.
Questions
How much tax will I pay if I sell all my stock at once?
It depends on how much of the gain lands in each capital-gain band once it is stacked on your other income, plus the 3.8% Net Investment Income Tax above the income threshold. In the example, a $500,000 gain on top of $200,000 of income costs about $97,639 in federal tax.
Does selling over several years always save tax?
No. It helps when a single-year sale pushes gain into a higher band or over the NIIT threshold. If your income is already high or the gain is small, the difference can be small, and the risk of holding a concentrated position while you wait can outweigh it.
What are the 2026 long-term capital-gain brackets?
For married couples filing jointly, long-term gains are taxed at 0% up to $98,900 of taxable income, 15% up to $613,700 and 20% above that. For single filers the thresholds are $49,450 and $545,500.
See the decision inside a full plan.
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