The Westport, Weston & Wilton Real Estate Report 2024

above: 3 Lowlyn Road, Westport: a 3,300-square-foot Colonial was torn down to make way for this 7-bedroom, 8,851-square-foot new build in Old Hill, listed at $3,999,000, by Michelle & Team at William Raveis

It’s a trick question, asking which neighborhoods are hot in Westport right now. And not only because it’s March and still too chilly to call anywhere hot. Icy winds, soggy rain, muddy hikes, bone-chilling polar-plunge temps—doesn’t matter. The actual answer is: All of them.

“Everything is hot right now because there is no inventory,” says Amy Curry of Berkshire Hathaway. It’s a refrain we’ve been hearing since Covid burst the dam holding back droves of diehard urban dwellers. They came flooding out to our area, their furrowed brows and dragging feet promptly turning to wide-eyed glee and leprechaun kicks: No more walk-up buildings! No more rats! No more malodorous subways! No more grilling of three-year-old Junior by finicky private-school panels! And look at the closet space (!), the mudrooms (!), the open space where Junior can play after … public school?!

One might surmise that the flood has slowed to a trickle by now, but it has not. Four years after a pandemic shot “privacy,” “open space” and “pool” up the must-have amenity list, families are still eagerly showing up from New York, New Jersey and beyond, looking for their little slice of Saugatuck Shores or Green’s Farms or Compo Beach, or Wilton, or Weston—whatever, just give us a piece!

“Right now in Westport, we have 60 houses to sell—60—which is crazy, because if you look back to December 2019, we had 247 houses on the market,” says Hope Klein at The Riverside Realty Group. “Everything is selling now. I’ve been in real estate here for thirty-three years. People used to want to be close to the train. They didn’t want a lot of land. You couldn’t give away Weston or Wilton. Covid changed everything. People want land. Work habits have changed. Everyone has pushed their boundaries farther north.”

25 Ryders Lane, Wilton: This 2,637 square-foot, 3-bedroom house with lots of open space sold for $1,551,000 by William Raveis

Droves of buyers are clamoring to get into any neighborhood here. “I had an open house this weekend [priced in the desirable $1.3 million range], and I had thirty to forty people in the house all day, every day, all weekend,” says Klein, who is seeing homes that used to be on the market a year, selling in a week. “People from the city see the lifestyle here. For $2 to $3 million for an apartment in New York, you get nothing. We show them they can live in 5 or 6,000 square feet, on an acre of land, with a great school system. We tell them about Longshore, the sailing school, the brand-new library, the chefs that have come out here from New York, the sophistication. People just come and so do their friends. And no one is selling because of interest rates or having no place to go.”

Robin Singer, at Coldwell Banker, comments, “Pre-Covid, three areas were most desirable: downtown, the beach and Green’s Farms. Everyone wanted easy access to the train. Old Hill was also desirable. You could not get a buyer to go to Coley if they worked in the city. Then Covid happened and people wanted to spread out. Suddenly two acres sounded great. Now buyers are not picky about location.”

Westport’s beach areas have experienced actual floods, not just floods of humans, in the not so distant past. “Climate change was a topic after [Hurricane] Irene and Sandy, but it’s amazing how people don’t talk about it anymore,” says Singer, regarding the continued popularity of beach neighborhoods. “If anything, I hear buyers hesitate due to it being more crowded down there, but not about the flooding. A lot of the houses are lifted now, so they are 14 or 15 feet up.”

She calls Compo Beach the “Rolls-Royce” of Westport’s beach areas, “because it has everything, but Saugatuck Shores has come into its own. People like it out there.” Singer is finding some Westporters wanting to take the Rolls-Royce for a spin, so they are renting on the beach to test it out. An inventory shortage means renting may be the only option for families looking for those entrancing water views.

Lower Weston, with easy access to the Westport area, is also popular. “People like Weston, and it has great schools. Since Covid, people are moving anywhere: Wilton, Redding, Easton,” adds Singer.

The Mill, 41 Richmondville Ave, Westport: 2-bedroom condos in this brand new luxury building begin at $1,399,000. The 3-bedroom penthouse, with its own roof deck, was still available as of press time, for $3,499,000. Listed by Coldwell Banker.

Mia Capella, at William Raveis, notes the serenity and rural ambience that draw buyers to Wilton and Weston. “Both have New England charm and a strong community spirit,” she says. “South Wilton has always been more desirable due to its proximity to major highways and public transportation, but all of Wilton and Weston’s ‘neighborhoods’ are desirable for many reasons, one of which is very low inventory! We need more homes to sell since both towns offer a vibrant cultural scene, historic character and harmonious coexistence with nature with lots of open space.”

Those in the market for luxury homes in the $4 or $5 million range can shop at a more leisurely pace. They are not flying off the market or as likely to draw bidding wars. Those on the other end, perhaps venturing over to Norwalk, get ready for the Black Friday of home shopping. “I put a little condo on in Norwalk on the river, in the $500,000s,” says Klein. “I had 38 showings in three days and 13 offers, well over $100,000 over asking.”

The best testament for this area being worth the money and scramble are young adults who grew up here, coming back. “My daughter lives here with her two kids, and they go to Coleytown just like she did,” says Klein. “She said, ‘Mom, it was so great growing up here, why wouldn’t I come back?’ A lot of her friends from Staples have also come back.”

Klein adds, “I think that Westport and Weston were always undervalued for what they offer. My gut is that eventually we will plateau. But I don’t think prices will go down. Interest rates are going to come down and then we will have more buyers than we have now.”

Read more online at

31 Woody Lane, Westport: This Milton Design 6-bedroom,10,390-square-foot home sits on 2 acres and incorporates a 100-year-old barn. Listed by The Riverside Realty Group for $6,000,000 (5+ months on the market).


Luxury Condos

With most smaller homes in Westport being razed and “Mcmansioned” by builders, some newcomers and empty nesters are turning to the new or remodeled plush condos around town. “Downsizers, people looking for second homes and a simplified lifestyle, often choose the high-end condos in Westport for their luxurious amenities and maintenance-free living,” says Capella. “They provide security and convenience in a much more manageable space.”

Bankside House, across the river from town, has 6 units left in the new 12-unit boutique building, each with its own private terrace. Prices range from $2,625,000 to $4,750,000 (mostly 2-bedrooms); Saugatuck River views, exquisite design and a prime location come at a price.

The Mill, on Richmondville Avenue near town, was just completed last month and one-third of the 31 units are under contract. Two-bedrooms start at $1,399,000 and the $3,499,000 penthouse, with 3 bedrooms and a private roof deck, is still up for grabs. Alexander Chingas, of the Bross Chingas Bross Team at Coldwell Banker, says, “The Mill is a fully serviced building with a concierge, a beautiful pool, a year-round outdoor hot tub, a gym, a great room, the Cafe co-working space, and a quiet roof deck.” Residents can cozy up to an outdoor fireplace and fire tables by the pool, and a furnished guest suite is available for visitors.

Other Westport condominium complexes—Harvest Commons, Regents Park, Landsdowne, and Terra Nova—have been around for decades. Buyers will find a range of prices, depending on whether units have been recently renovated or not. All have pools and all but Terra Nova have tennis courts as well.

Condo Sales Snapshot: 2023

24 condominiums sold in Westport
Lowest sale price: $455,000
Highest sale price: $4,560,870
Average sale price: $1,370,414
Median sale price: $847,750
List-to-sale price ratio:
10% under to 26% over

The Mill condo photo by Modern Angles; the Ryder Lane photo by Listing style; Woody Lane photo by Realty Plans; other photos courtesy of realtors

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