Fairfield County's Most Expensive Home Sales, Town by Town

Three of the biggest home sales here in Fairfield County over the past year happened within eight days of each other last November. On November 14, a private island off Long Neck Point in Darien sold for $26,500,000. Five days later, a waterfront estate in Greenwich's Mead Point Association was recorded at $40,000,000, and on November 21, four waterfront lots on Beachside Avenue in Westport sold together for $45,000,000.

Being an active Realtor in the area, I have a pretty good sense of where the high end tops out in each town, but I wanted to see what the top sale actually was in every town I cover, and how the homes closest to the top sold, so I went through every single-family home that closed in Greenwich, Darien, New Canaan, Westport, Wilton, Ridgefield, Fairfield, Stamford and Norwalk between October 1, 2025 and September 30, 2026. That came to a total of 3,016 sales on SmartMLS. Greenwich also runs its own MLS, so for Greenwich's top sale I used the town's property transfer records.

As it turns out, the top sale ranged from $45,000,000 in Westport all the way down to $4,300,000 in Wilton, and how competitive the bidding got depended much more on the price than on the town. Most homes kept selling over asking right up to the $5,000,000 price point, where above that, sales above asking price began to taper off.

The Top Sale in Each Town

Westport: $45,000,000. The largest sale in any of the nine towns was four waterfront lots at 120 through 128 Beachside Avenue in Greens Farms, which sold together to one buyer for a combined $45,000,000. The estate covers about 13.2 acres on Long Island Sound, with homes, a pool and a tennis court, and two of the lots were once owned by Phil Donahue and Marlo Thomas. The sale was recorded as two transactions, of $24,210,000 and $20,790,000, and the Westport Journal reported it as what is thought to be the largest residential sale in Westport's history. I covered it in more detail in my Greens Farms neighborhood guide. The next-highest Westport sale was also on Beachside Avenue, a 1926 Tudor on 3.55 acres that sold for $15,500,000 in March.

Greenwich: $40,000,000. 579 Indian Field Road in the Mead Point Association was built in 2013, with about 11,500 square feet on 2.72 waterfront acres, and according to Patch it looks south and east across Long Island Sound toward Tod's Point, with its own floating dock. The house went under contract in August while listed at $43,000,000 and closed at $40,000,000. Because it was listed through the Greenwich MLS, it does not appear in the SmartMLS data behind the rest of this post, and its price comes from the town's property transfer records. The highest Greenwich sale on SmartMLS was 382 North Street, a newly built home of 14,126 square feet on 2.39 acres that went under contract in 30 days and closed at $16,500,000 in December. If you are wondering about 214 Clapboard Ridge Road, the $43,500,000 sale that made headlines last year, it closed in August 2025, a few weeks before the period covered here.

Darien: $26,500,000. Hay Island is a private island of about 18 acres off Long Neck Point, reached by a gated causeway, and it came to market for the first time in over 100 years as the last piece of the Ziegler family's Connecticut holdings (William Ziegler co-founded the Royal Baking Powder Company). Along with the 8,684 square foot main house, built in 2010 and designed by Mac Patterson of Austin Patterson Disston, the island has a guest house, a pool house, an infinity pool, two sandy beaches and a dock. Hay Island was first listed at $35,000,000 in March 2025, reduced the listing price to $29,500,000 in May, and closed at 89.8% of that reduced price after 244 days on market. That was roughly double the next-highest Darien sale, a 1937 colonial on 9.26 acres on Hollow Tree Ridge Road that sold in July for $13,000,000. As big as the sale was, it is not a Darien record. The same family sold Ziegler Farm for $57,500,000 in 2023, and the Town of Darien bought Great Island, just across Ziegler's Cove, for $85,000,000 that same year.

Fairfield: $12,000,000. In Southport Village, 260 Willow Street sold at its full list price of $12,000,000 in April after 281 days on market. The contemporary has 8,119 square feet on 1.27 acres, along with a guest house, a pool and a pool house. Architect Christopher Pagliaro reimagined the whole estate under what the listing described as a philosophy of "addition by subtraction." The house sits a short walk from Southport Harbor rather than on the water itself. The next-highest Fairfield sale was a 1926 colonial on Sasco Hill Road at $9,050,000.

New Canaan: $10,025,000. Known as Orchard's End, 544 Oenoke Ridge is a 1929 Tudor estate on 6.26 acres, designed by William B. Tubby, the architect behind Waveny House. Starting in 2014, the owners spent several years renovating and expanding the estate with architect Dinyar Wadia, adding a guest house and a 5,000 square foot wellness center. The great room was inspired by Duart Castle on Scotland's Isle of Mull. Orchard's End was listed at $13,900,000 in the Spring of 2025 and sold for $10,025,000 in November after 209 days on market. New Canaan's top sales were the most tightly grouped of the nine towns, with all five of its highest sales landing between $8,000,000 and $10,025,000.

Norwalk: $10,000,000. 10 Shorehaven Road, a Nantucket-inspired house in the Shorehaven section of Norwalk, sold for $10,000,000 on September 21, 2026, compared to a list price of $11,500,000. Built in 2000, the house has 9,564 square feet and five en-suite bedrooms on just over an acre directly on Long Island Sound, with a pool, a spa and a private dock. Norwalk's median single-family home sold for $815,000 over the same period, and its next two highest sales were both in Rowayton, at $6,950,000 and $5,350,000.

Ridgefield: $6,400,000. 384 West Lane, a Georgian manor of about 7,500 square feet on 13.06 acres along the New York line, sold for $6,400,000 in April, compared to a list price of $7,000,000. The property was once an equestrian farm, and its nine-stall barn has since been turned into an entertainment pavilion, alongside a stone cottage, a three-bedroom guest house and a six-car heated garage with a studio above it. The kitchen and the living spaces around it were designed by Dinyar Wadia, the same architect who renovated New Canaan's top sale, so his work shows up in two of the nine top sales.

Stamford: $6,014,250. Stamford's top sale was really about the land. 250 Davenport Drive covers 1.68 acres at the very end of Southfield Point, with water on three sides and views to the east, south and west, it came to market for the first time in 76 years. The 1950 house on the property was marketed as a blank canvas, with a survey and a feasibility study already completed for the next owner's plans. Listed at $5,495,000, the property went under contract in 22 days and closed at $6,014,250, or 109.5% of its list price. The next-highest Stamford sale was 336 Ocean Drive West in Shippan, a 1915 colonial of 8,107 square feet on 1.1 acres, at its full list price of $4,500,000.

Wilton: $4,300,000. Wilton's top sale drew the kind of competition you would normally expect much further down the market. 7 Spruce Meadow Court, a gated colonial in South Wilton built in 1999 with 11,410 square feet, a tennis court and a heated pool on 2.36 acres, was listed at $3,995,000 and went under contract in just 7 days. It closed at $4,300,000 in August, or 107.6% of its list price.

The Waterfront Premium

Five of the nine top sales sat directly on Long Island Sound, in Westport, Greenwich, Darien, Norwalk and Stamford, and Fairfield's was a short walk from Southport Harbor. Those six shoreline towns also had the widest gaps between their top sale and their median sale, from about 6 times the median in Stamford to more than 18 times in Westport, compared to between about 3 and 5 times in the three inland towns, New Canaan, Ridgefield and Wilton.

Price per square foot, which takes the size of the house out of the equation, shows the same thing. Hay Island sold for about $3,052 per square foot and the Beachside Avenue estate for about $2,850 per foot, compared to $774 for the median home in Darien and $629 for the median home in Westport. On the other end, the top sales in Wilton and New Canaan actually sold for less per foot than the median home in town, $377 compared to $431 in Wilton and $557 compared to $613 in New Canaan, because the most expensive homes in those towns were also among the biggest. Ridgefield was the exception among the inland towns, at $849 per foot compared to $399 for the median Ridgefield home, and its top sale came with 13 acres of land.

Where the Bidding Wars Stop

Across the nine towns, 62.4% of single-family homes sold over asking during the period, at a median sale-to-list price ratio of 102.8%, meaning that $100 in asking price led to about $102.80 in closed sales. As you would expect, competition was strongest further down the market, with 70% of homes between $1,000,000 and $2,000,000 selling over asking, but it also held up well further up the ladder. Between $3,000,000 and $5,000,000, 58% of homes still sold over asking, and the median home went under contract in 17 days, about the same pace as homes under $1,000,000.

Above the $5,000,000 price point, homes sold very differently. Only 32% of the 111 homes that sold between $5,000,000 and $10,000,000 went over asking, and the median home took 40 days to get under contract. Of the 17 homes that sold for $10,000,000 or more on SmartMLS, none closed over asking, just two sold at their full list price, and the median sale closed at 92.3% of its list price after 91 days on market.

What surprises me most is how little the town mattered. Between $3,000,000 and $5,000,000, homes in Wilton, Stamford, Ridgefield, Norwalk and Fairfield sold over asking 59% of the time, compared to 58% for homes in the same price range in Westport, Greenwich, Darien and New Canaan. That goes a long way toward explaining why Wilton's most expensive homes sold over asking and Westport's did not. Wilton was the only one of the nine towns where the top tenth of sales, everything from $2,250,000 up, sold over asking more often than the rest of the town, 81% compared to 74%, and 9 of its 10 highest sales went over asking, seven of them under contract within 16 days. In Westport, where even the tenth-highest sale was $7,750,000, none of the ten highest sales went over asking. In Greenwich it was one of the top ten, and in Darien, two.

What This Means If You Are In The Market

If you own a home that would sell for under $5,000,000, which includes most homes in every one of the nine towns, the competition you have been hearing about has most likely held at your price point. Most homes in the $3,000,000 to $5,000,000 range still sold over asking during the period, and they sold quickly.

Above $5,000,000, pricing matters a lot more. Homes at that level usually take weeks or months to get under contract rather than days, and the closing price is more often negotiated down from the list price than bid up. These homes are still selling, with 17 of them closing at $10,000,000 or more on SmartMLS alone, but buyers at that level have more room to negotiate, and that shows up in the closing price.

Buyers shopping above $5,000,000 should know about that room before writing an offer. In Wilton, or anywhere the top of the town's market sits under $5,000,000, plan on competing for the best house in town the same way you would for a starter home.

If you are thinking about buying or selling at the upper end of the market here in Fairfield County, I'd be happy to go over the recent sales that compare most closely to your home, or to the one you have your eye on. And if you just want a starting point, my free home valuation gives you an estimate in about a minute!

A note on methodology: figures come from SmartMLS records for single-family homes in the nine towns named at the top that closed between October 1, 2025 and September 30, 2026, pulled October 11, 2026. Greenwich's top sale, 579 Indian Field Road, was a Greenwich MLS listing and its price comes from town property transfer records as reported by the Greenwich Free Press, Patch and CT Insider. Property details for individual homes come from the listings and from Patch, the Westport Journal, Cottages & Gardens and the New Canaan Advertiser; every other Greenwich figure here excludes Greenwich MLS listings, so Greenwich activity is likely understated. Westport's top sale is the combined price of two recorded sales, covering four lots, bought together as one estate; in the price-band and top-ten figures, each recorded sale is counted separately, as SmartMLS records them. Over asking compares the closing price to the final list price. Days on market are as SmartMLS reports them, counted from the listing date to an accepted offer, so they run shorter than the time from listing to closing. Town medians are the median closing price of single-family homes in that town over the same period. These figures describe the market as a whole and are not a valuation of any individual home.