Greenwich, CT real estate has rewarded long-time owners more than almost any market in the country, with the median single-family sale price at $3,710,000 in 2026, up from $1,866,000 in 2019, according to the Greenwich Multiple Listing Service. If you have owned your home for 25 years or more, that appreciation is real. So is the question of what it means for a sale. The right answer depends on your numbers, so call me and I will help you see where you stand before you decide anything.

Why Do Long-Time Greenwich Owners Feel Stuck?

Most long-time owners are not stuck because of the market. They are stuck because of the tax bill. Under current federal law, a single filer can exclude up to $250,000 of gain from the sale of a principal residence, and married couples filing jointly can exclude up to $500,000. Those limits apply when ownership and residency requirements are met. They have not been adjusted for inflation since 1997. 

A home bought in Greenwich 25 years ago may have gained far more than that. This is often called the lock-in effect, and it keeps good homes off the market.

What Could a Sale Look Like in Numbers?

Here is a simple, hypothetical example. It is not a tax calculation, and every situation is different.

Connecticut income tax may apply on top of that. Your actual bill is usually lower, because capital improvements raise your cost basis and selling costs reduce your gain. This is why keeping your renovation receipts matters.

What Are Your Options After 25 Years in Your Home?

There is no wrong answer here. The mistake is deciding without the full picture.

Could the Rules Change?

Possibly, but planning around a bill that has not passed is a gamble. The More Homes on the Market Act (H.R. 1340) would raise the exclusion to $500,000 for individuals and $1 million for married couples filing jointly. As of August 2026 it had picked up meaningful support in Congress, but it had not become law. I track this closely and will update you as it moves. My advice is to plan around today's rules and treat any increase as a bonus. 

What Is the Greenwich Market Doing for Sellers Right Now?

Conditions favor sellers who are prepared:

• Most homes sold above list price. Of 282 single-family sales from March through August 2026, 58.5% closed over asking, with an average premium of 11.9% over list price.

• Well-priced homes move fast. Those over-list sales averaged 21 days on market, compared with 113 days for homes that sold under list.

• Volume is steady, not surging. Annual single-family closings have held near 500 to 520 for three years, so buyers are competing for a limited supply of homes.

Pricing is what separates the fast sales from the slow ones, and it is where 40 years in Greenwich matters.

What Should You Do Before You Decide?

Start with three steps:

• Find your cost basis. Gather your original closing documents and every major improvement receipt.

• Talk to a CPA. Ask about your exclusion, your basis, and Connecticut tax. I am not a tax advisor, and you should not rely on me for tax advice.

• Talk to an estate attorney. If leaving the home to heirs is on the table, the stepped-up basis may change your answer.

Then call me. I can tell you what your home would likely sell for, how buyers would respond, and what your net could look like once your CPA supplies the tax piece. I am happy to coordinate with your advisors.

Russell Pruner | Senior Real Estate Specialist | CRS | GRI | SRES | Six-Time GAR-GMLS President | 40+ Years  in Greenwich | Greenwich Streets Team at Compass 

The Greenwich Streets Team has been named RealTrends Verified for 2026, placing them among the top 1.5% of real estate  professionals nationwide. 

Frequently Asked Questions

How much capital gains tax will I owe if I sell my Greenwich home after 25 years?
It depends on your cost basis, your improvements, and your filing status. You can exclude up to $250,000 (single) or $500,000 (married filing jointly) of gain. Gain above that is generally taxed at federal long-term capital gains rates, and Connecticut income tax may also apply. A CPA can calculate your number.

Does the capital gains exclusion apply to every long-time owner?
Generally you must have owned and lived in the home as your principal residence for at least two of the five years before the sale, and other IRS requirements apply.

Can improvements to my home reduce my tax bill?
Yes. Capital improvements such as additions, renovations, and major system replacements can increase your cost basis and reduce your taxable gain. Keep your receipts.

What happens to the tax basis if my heirs inherit my home?
Heirs generally receive a stepped-up basis to the home's value at the date of death, which can significantly reduce or eliminate the gain if they sell. Confirm this with an estate attorney.

Is the capital gains exclusion going to increase?
Legislation to double it and index it to inflation has been introduced, but as of August 2026 it had not become law. Plan around the current limits.

How do I find out what my Greenwich home is worth?
The most reliable way is a market analysis based on recent Greenwich Multiple Listing Service sales for comparable homes, not an online estimate and I can supply you with that.

Ready to See Your Real Numbers?

Twenty-five years of ownership is a big asset, and you deserve a clear plan for it. Call me at 203-524-4998 or email [email protected], and I will walk through your options with you and your advisors, with no pressure and no obligation.

Last Updated October 2026

Source: Greenwich Multiple Listing Service, Inc. Figures reflect single-family sales through August 2026. This article is general information, not tax or legal advice.
Last updated: October 2026