Greenwich’s State Of Real Estate in 2025

Cash deals, Speed sales and luxury listings—what it takes to buy and sell in Greenwich today.

It should be easier to buy a house in Greenwich. For years, the market here was a finely tuned machine, one that dealt with the occasional rude shocks in the economy with calm fortitude. But the rules seem to change every year. Outside forces have infiltrated our quiet world and made it shockingly competitive.

The numbers today appear quite exalted, so much so that the year started with nothing available under a million and only eight houses available under $2 million. And should a fresh house appear in the listings, it’s not there for long.“The average days on the market last year was twenty-four days,” reports Pam Pagnani of Sotheby’s. “In 2023, it was thirty-five days. So things are moving more quickly.” “If you’re dealing in the $4 million-and-under market, you’ve got to be ready to fly,” says Jennifer Leahy of Douglas Elliman. ”I’ve seen deals close in forty-eight hours.”

What we’ve found post-Covid is that the neighborhoods are less important,” says Jeff Jackson. “Now it’s the property itself and not the location. That’s a big shift.“It used to be what school you went to. Now it’s driven more by the age of the house, new construction, ceiling height and finishes. These are things the drive demand. Location is still important, and if you can command all, you get astronomical results.”

One of the biggest sales (at least among the publicly discussed) was the waterfront Robert Steinberg mansion that went for $31.5 million. It had been on and off the market over the years, and a decade ago the ask was $54 million before the reductions. Perhaps its provenance proved decisive. Back in 1982, the 5.8-acre estate was bought by Donald Trump and then-wife Ivana. After their 1992 divorce, it was Ivana’s until she sold it in 1998. (Joseph Barbieri of Sotheby’s International brought the buyer, and Rob Johnson of Brown Harris Stevens represented the seller.)

But most often, prices rise, and sometimes to surprising amounts. Viewing the price histories of properties can lead to some confounding revelations. Raveis handled both sides of a sale at 248 Round Hill Road, a 3.41-acre, 9,800-square-foot estate that closed in late fall for $11.4 million. That is not an unfamiliar sum for mid-country, but, wait a minute, the property sold a couple years ago for $3.5 million. That would be called adding value.

Another intriguing price history was seen at 543 Stanwich Road, which Jen Danzi Real Estate was happy to move for $16.2 million; the listing agent was Jesse Marinak of Serhant. But didn’t that property sell ten years ago for $2.8 million? “That house was torn down, and they built a brand new one,” Jen responds. “That shows what you can do when you invest in a new home.”

BUYER’S PLAYBOOK

Be Prepared
Listings can disappear in a day—have your game plan ready.

Know Your Budget
Understand your financial limits before falling in love with a property.

Prioritize Location
Think beyond the house—consider schools, commute times and neighborhood offerings.

Trust Your Instincts
If a home feels right, make the offer!

Cover story project build by SBP HOMES
Architecture: Tanner White Architects

Written by Chris Hodenfield
Photograph By Kyle Norton