Taxes in retirement
A tax guide tells you the rules. Your Checkup applies them to your home, your accounts and your state.
Most retirement tools leave taxes out, or apply one flat rate to everything. But the taxes that matter most in retirement depend on details only you know: what you paid for your home, whose name is on the deed, where you live, and when you might sell. Your Checkup works from those details.
What your Checkup looks at
If you plan to sell your home
We estimate the tax using your expected sale price, what you paid, your selling costs and how you file, including the home-sale tax break, federal tax and your state's tax.
If you own a rental or second home
We estimate the tax on a sale, including the part that comes from depreciation, and lay out your options side by side: swapping into another property, moving in first, or keeping it for your heirs.
If you're married
We look at how your home is owned and show how that changes the tax if one of you dies first. For some couples, the timing of a sale can change the bill by hundreds of thousands of dollars.
Your property tax
We list the property-tax relief programs worth checking for your address, from homestead exemptions to senior freezes and deferrals.
When one of you is gone
We show how the survivor's taxes change once they file as a single person, using your own incomes, and what you can do about it now.
Your estate and your state
We compare what you own with the federal and your state's estate-tax limits, and put retirement-account deadlines on your calendar.
What you’d see · Sample
If you sell your home
Carol, 67, and Dennis, 70, in Virginia. They bought their home in 1994 and plan to sell in 2030.
You paid $210,000 for your home and have put about $90,000 into improvements, so your basis is about $300,000. At your expected sale price of $1,150,000, less about $69,000 in selling costs, your profit would be about $781,000. As a married couple, the first $500,000 is tax-free.
On the remaining $281,000, we estimate about $40,600 in federal tax, including the 3.8% net investment income tax, and about $16,200 in Virginia tax: roughly $56,800 in all. Your forecast sets that amount aside from the sale.
Timing matters for you. Because you own the home jointly, if Dennis died first, half of it would get a new basis at its value then. If Carol sold within two years of his death, she could still use the $500,000 limit, and the estimated tax would fall to about $0. After two years, the single limit of $250,000 would apply. This is worth raising with your tax preparer before you list the house.
From a sample Checkup for a fictional household. Your Checkup is written from your own answers.
How it ties into the rest of your plan
- The tax on a planned sale comes out of the money your forecast counts on, so your plan reflects what you'd really keep.
- If the amount you've set aside for taxes on a sale looks too low, we flag it on the first page.
- The best timing for a home sale appears next to your housing decision, not buried in a tax chapter.
Background reading
- Selling your home in retirement: what you'll oweHow the home-sale tax break works, how to figure your profit, and what married couples and surviving spouses should know before they sell.
- Rental and second homes: the tax when you sellWhy the tax bill on a rental or vacation home is often bigger than people expect, and the common ways to lower or delay it, explained in plain language.
- Property tax relief for older homeownersHomestead exemptions, senior freezes, income-based credits and deferral programs: what they are, who they help, and why you usually have to ask.
- Estate tax: who actually owes itThe federal limit is $15,000,000 per person in 2026, so few families owe it. State estate and inheritance taxes start much lower. Here's how they work.