122 Beachside Avenue—this Compass listing, with epic Gold Coast views, was part of a record-breaking $54 million sale last year.
The real estate roller coaster analogy has come up before, but the ride the Westport/Weston/Wilton market offers is not really that. Roller coasters go up and down. This ride mainly goes up. The line to jump on is still snaking from here to New York City and beyond. Riders are likely to experience the usual hefty price ascents with a shortage of places to jump off, but these riders have iron stomachs; they’re hanging on and playing hard. There may be a few unexpected twists and turns but, by and large, it’s a ride sellers and buyers have come to know well since the flood of Covid transactions drained the market of inventory.
However, Meredith Kamo at Compass is noticing some interesting shifts lately. “The market is so unpredictable at the moment. Seasonality is no longer a factor. One week open houses are packed: the next, they are empty,” she says. “I think a lot has to do with how buyers are feeling about the state of the world on any given week. When they are scared for the future, they want to hunker down, by either moving to the suburbs from the city or moving within town to something that offers them a different opportunity.”
This 6-bedroom/9-bathroom home at 39 Compo Parkway promises a perma-staycation, with resort amenities, natural beauty and unmatched privacy. With over 11,000 square feet and over 2 acres of property, this sanctuary is listed at $12,950,000 by Michelle & Team at William Raveis.
THE NUMBERS
“Last year felt like the same market as 2024 with sharper edges,” says John Raus at Berkshire Hathaway. “Inventory remained tight and demand stayed strong, but buyers became more selective. The best homes still sold quickly, and everything else had to work a little harder.”
WESTPORT
• Median Single-Family Sale Price (YTD): $2,300,000 (+6.4% YoY)
• Average Sale Price (YTD): $2,746,382 (+10.6% YoY)
• Closed Sales (YTD): 299 (-2.9% YoY)
• Months of Inventory: ~1.6 months
• Percent of List Price Received: 102.2%
WESTON
• Median Single-Family Sale Price (YTD): $1,399,000 (+3.6% YoY)
• Average Sale Price (YTD): $1,531,804 (+4.3% YoY)
• Closed Sales (YTD): 145 (+7.4% YoY)
• Months of Inventory: ~1.7 months
• Percent of List Price Received: 102.7%
WILTON
• Median Single-Family Sale Price (YTD): $1,350,000 (+11.6% YoY)
• Average Sale Price (YTD): $1,452,260 (+8.6% YoY)
• Closed Sales (YTD): 205 (-12.8% YoY)
• Months of Inventory: ~1.1 months
• Percent of List Price Received: 106.5%
(Statistics courtesy of the Riverside Realty Group)
“Westport really didn’t cool off; it just normalized at a very high level,” says Raus. All stats reflected an ever-stronger market in Weston. While transactions declined slightly in Wilton, median single-family-home price jumped 11.6 percent and homes flew off the market with an average of 1.1 months of inventory. Meredith Kamo comments, “Homes under $2 million are selling fast with multiple offers because, at this point, they are so few and far between. But over-$20 million homes are also selling (albeit slower) in Westport, which is historically unprecedented.”
In November, a record breaking $54 million landed a new family in town a stretch of the Gold Coast that encompasses five adjacent waterfront properties on Beachside Avenue (including a home once owned by Phil Donahue and Marlo Thomas and lots where Harvey Weinstein’s mansion was razed). The listings were with Compass and the buyer was represented by Raus, who has a 6,950-square-foot home at 69 Beachside Avenue hitting the market now. The four-acre property, with pool, tennis court and gym, used to be part of the JC Penney estate.
THE LIFESTYLE
A buzzword now is lifestyle. Sellers are not just presenting a home layout; they are laying out a lifestyle. If what they are hawking conveys easy, breezy, comfortable and luxurious, then house hunters are buying.
“People want to feel comfortable and enjoy their homes to the fullest,” says Kamo. “They want amenities like golf simulators, cold plunges, saunas, gyms, pools and paddle courts—all the bells and whistles that make it so they don’t have to leave their houses. I think a lot of that is also due to the ‘hunker down’ mentality being fueled by uncertainty in the world.”
Michelle Genovese, of Michelle & Team at William Raveis, says, “Buyers today, especially from the city, want homes that feel light, updated and effortless. Open layouts, great kitchens, home offices and indoor/outdoor living are still important, along with pools, generators, EV chargers and modern primary suites.” City slickers also love walkability. If the town, beach, schools or Longshore are down the street, the homes are in demand. “Buyers continue to gravitate toward modern farm houses and transitional styles,” says Genovese. They want “wellness living,” with the saunas and gyms Kamo mentioned, and “abundant natural light and calm, thoughtfully designed outdoor spaces,” adds Genovese.
Genovese continues, “What’s notable: it’s not always about size; it’s how a home lives. We recently sold a home close to town that was less then 5,000 square feet, but it lived beautifully. It attracted multiple offers from both New York City and local buyers, which seems to show what matters now is how a home feels, not how it measures.”
Raus adds, “In Westport, location plus lifestyle trumps pure square footage: that is walkability to town, beaches, Longshore, schools or an easy commute setup.” Move-in ready is also a top priority. “In 2025, if a home needed updates but priced like turn-key, buyers moved on instead of making it work,” says Raus. “There was also increased awareness around future costs of insurance, utilities and maintenance. Buyers didn’t just shop price, they shopped future hassle.”
69 Beachside Avenue—this 7,000-square-foot home with 6 bedrooms and 7 bathrooms is about to hit the market through John Raus at Berkshire Hathaway.
Hedyeh Renstrup at William Pitt Sotheby’s noticed a new “must-have”: the double suite. “Buyers are now explicitly asking for two primary suites—one for the owners and a second, equally luxurious, first-floor suite for aging parents,” she says. “We’ve seen a shift toward properties that can accommodate Accessory Dwelling Units (ADUs). Whether it’s a sophisticated cottage for a returning adult child or a private wing for a live-in care provider, flexibility is the new ultimate luxury.”
THE DEAL
Sellers are looking for certainty, so removing any guesswork is the name of game in closing a deal. Cash is king—and there seems to be plenty to go around. “A striking trend in 2025 was the rise of the all-cash luxury buyer, often Millennials or Gen-Xers,” says Renstrup. “This was largely fueled by an estimated $6 trillion in wealth changing hands globally in 2025 alone. To win in a low-inventory market, many families are using ‘family-funded bids.’ They use generational wealth to make an all-cash offer to win the bidding war, then refinance into a traditional mortgage later.” She says about a third of young buyers used a gift or loan from family to secure their dream home here. Estate tax exemptions dropping by half at the start of 2026 fueled an unprecedented “flurry of high-end activity in December,” noted Renstrup.
For those who can’t dig enough coins from the family coffers or couch cushions, all is not lost. “Working with a lender who can fully underwrite a buyer in advance removes a major contingency and allows the offer to compete more like cash,” explains Raus. “Winning offers consistently show strong pre-approval or proof of funds, clean timelines, minimal ambiguity, and flexibility around closing when possible. Shortening inspection windows, rather than waiving it, and completing pre-offer walk throughs on competitive homes can help make your offer stronger.”
Raus sees deals fall through when surprises come up in inspections and contract terms are murky: “For sellers, I often recommend completing an inspection upfront, which builds trust with buyers and supports the home’s pricing by showing everything was considered from the start. The homes that sell almost immediately are priced correctly, present well and are matched with buyers ready to move decisively from day one.”
For families in flux and those looking to have their kids settled into a new school district by fall, figuring out where to live while awaiting their dream-home deal is tough. The rental inventory is tight but pandemic rental prices that drove people from here to the Hamptons to find more affordable options (!) seem to have settled down a bit. “Renters are active, but just like buyers, they’re selective,” says Raus. “Pricing and condition matter more than ever with the average monthly rental price falling between $6 and $7,000.” Of course a summer rental on the Sound may nab quadruple that.
These renderings show the 5-bedroom home with gunite pool under construction at 2 Fairport Road. This well-situated home is listed at $2,600,000 through Kristi Law at William Pitt Sotheby’s
2026 AND BEYOND
Raus expects the real estate market in our area to continue to be strong, with properly priced homes moving fast. “Heading into 2026, I don’t see there being any shortage of buyer competition as inventory comes to market this spring. Buyers will continue to pay up for turn-key and negotiate for what’s not, so getting pricing right from the start is critical,” he says. “If mortgage rates ease further, you may see more sellers leave their historic low rates, but any economic uncertainty could easily create a two-speed market where the best homes sell fast and everything else needs to be priced more thoughtfully.”
In her crystal ball, Renstrup sees a “great unlocking” in ourfuture. “We expect 2026 to see an 8.9 percent increase in existinghome inventory as more Boomers finally decide to ‘gift’ their larger estates to the market, while moving into more manageable,high-amenity local condos,” she explains. “We aren’t seeing a crash; the influx of generational wealth will keep Westport’s price floor high, ensuring the town remains one of the most resilient real estate markets in the Northeast.”