If you are about to close on a business sale, the house you want in Greenwich may be harder to find, and more expensive, than it looked a year ago. The latest local data shows a market with very few listings, fast sales and prices still climbing.

The market in brief

Greenwich recorded only 37 single-family sales in August 2026, the lowest August this century apart from 2009. Yet the median sale price rose 41% to $3.95 million. The story is supply: according to Greenwich Association of REALTORS data, active single-family listings at the end of August were down 29% from a year earlier, and homes that did sell averaged 17 days on market and closed at 103.6% of list price. With so few sales, a handful of large closings can move the monthly median a long way.

The year-to-date numbers are steadier. Through July, 305 single-family homes closed at a median of $3.6 million, up 14% from the same period in 2025. Sales volume was nearly flat, so the gain came from price, not activity.

Two markets, not one

The town behaves differently by price band:

  • Under $4 million: tight. Inventory in this range is thin across the whole town, and buyers should expect competition on move-in-ready homes.
  • $8 million and up: looser. Sellers in this range have more room to negotiate. Sales between $6.5 million and $10 million nearly doubled through August, from 21 to 41.

Condos are the one segment where supply is rising. The year-to-date condo median through July topped $1 million ($1,075,000), and new condo listings nearly doubled in August.

Why owners in Greenwich are not selling

Local analysts point to a few reasons: retirees with little to trade down into, Connecticut's tax on capital gains (taxed as income, at up to 6.99%), and the real estate conveyance tax. For a business owner, the tax points matter a great deal. A large sale can carry a significant tax bill before the proceeds ever reach a closing table.

That is the real planning question. If your liquidity event is funding a Greenwich purchase, the timing and structure of the sale affect how much home you can afford, and when.

What to do before you tour

  1. Model the proceeds, not just the price. Estimate the taxes on the business sale, including Connecticut income tax on the gain, before you set a home budget.
  2. Get pre-approved early. Under $4 million, your offer will compete with others.
  3. Check the property tax math. Greenwich's mill rate and reassessments change the monthly cost. Verify them against the purchase price you are considering.
  4. Know the transfer costs. Sellers generally pay Connecticut's state conveyance tax, which is tiered: 0.75% on the first $800,000, 1.25% from $800,000 to $2.5 million, and 2.25% only on the portion above $2.5 million. Greenwich adds a 0.25% municipal tax on the full price. Factor this in if you are also selling a home.
  5. Consider renting first. If the numbers are still moving, a year of renting lets you learn the neighborhoods and avoid overpaying in a tight market.

Where to look

Neighborhood prices vary a lot. Through July, Riverside's median was $3.68 million, Old Greenwich's $3.53 million and Cos Cob's $2.4 million, with Cos Cob the least expensive but up 20% year over year.

How we help

Smarter Mergers advises owners on the sale of their business, from valuation and exit readiness to negotiation and close. We work alongside your tax advisers and lawyers so the structure and timing of the sale support what comes next, including a home purchase. If you are planning a sale in the next year or two, we welcome a confidential conversation.

Market figures come from Greenwich Association of REALTORS and Greenwich MLS data as reported by Living by the Sound, Greenwich Streets Team and Anderson Associates. Tax rates are as of October 2026; confirm them with your tax adviser.

For information only. Not investment, legal or tax advice. See our Disclaimer.