Greenwich’s luxury home market booms — and it’s anything but cheap

The luxury housing market in the famously wealthy New York City suburb of Greenwich, Connecticut, is on fire, not literally but in terms of sale — and it’s not even the end of the year yet.

According to data compiled by Compass agent Mark Pruner, 25 homes priced above $10 million have already sold in Greenwich through August, the most in any full year since 1999. At the current sales pace, Pruner estimates that the town’s ultra-luxury market could end 2025 generating an unprecedented $579 million in sales — nearly double the $314 million record set in 2023.

Brokers say the buying frenzy is being fueled by strong Wall Street returns and political jitters among wealthy New Yorkers, some of whom are looking to hedge against market uncertainty ahead of the city’s mayoral elections. The combination of stock market gains and a desire to move money into tangible assets is pushing high-net-worth buyers to act fast.

“People are choosing to cash in their stock gains now rather than wait and risk a downturn,” Pruner said.

One of the biggest sales of the year so far was a three-story custom-built mansion at 214 Clapboard Ridge Road, which sold for $43 million in August. 

The property, set on eight acres, boasts of eight fireplaces, a limestone foyer and a glass elevator. Initially listed for $55 million, it went under contract in just 42 days — unusually fast for a home at this price point, where sellers are typically told to expect 200 days to a year on the market.

Michele Tesei of Houlihan Lawrence, the agent behind the record deal, said she has been seeing surprisingly young buyers, mostly couples under 40 — entering the ultra-luxury market. She credits generational wealth transfers from baby boomers to their children as another factor keeping demand high.

The rush in Greenwich mirrors a broader trend across elite U.S. enclaves. The Hamptons crossed a milestone earlier this year, with median home prices topping $2 million for the first time, while Manhattan’s luxury market had its strongest first quarter in six years.

All this comes as the rest of the housing market struggles. Elevated borrowing costs have left average buyers on the sidelines, but affluent cash buyers are continuing to snap up trophy properties — and in Greenwich, they’re doing it at a historic clip.

Greenwich’s luxury scene isn’t just heating up — it’s sizzling. And for deep-pocketed buyers, there’s no sign the spending spree is slowing anytime soon.