WESTPORT, CT — Westport's shoreline sets the top of its housing market. All five of the town's most expensive homes for sale on Zillow.com are priced above $10 million, led by a $22.8 million modern house planned on the water in Greens Farms.
No. 1 on the list is new construction by Coastal Luxury Homes at 11 Beachside Common in Greens Farms, listed at $22,825,000. The planned modern house, spread over four levels on 2.6 waterfront acres, will have 12,946 square feet, eight bedrooms, eight full bathrooms and two half bathrooms, with walls of glass facing Sherwood Island, Burying Hill Beach and Long Island Sound. It has been on Zillow for 223 days.
Just behind it is a gated waterfront estate at 279 Saugatuck Ave., at $14,900,000. The 1999 house faces east over the Sound from walls of windows, French doors and balconies, and has 9,546 square feet, five bedrooms, six full bathrooms and two half bathrooms on 1.35 acres. Outside are a screened porch, a gunite pool and spa, an outdoor bar with a grill, a fire pit and a 168-foot seawall. It has been on Zillow for 145 days.
Rounding out the top three is a new, finished house steps from Compo Beach at 14 Owenoke Park, listed at $10,985,000. The 6,050-square-foot home has five bedrooms, each with its own bath, plus two half bathrooms on 0.79 acres, and the listing says it fully meets FEMA flood standards. It has a pool and spa, water access on Gray's Creek, views of the Sound, an elevator, a sauna in the primary suite and a kitchen with two islands. It has been on Zillow for 39 days.
No. 4 is another Coastal Luxury Homes project, to be built at 11 Dogwood Lane, at $10,650,000. The 9,100-square-foot plan on 1.87 acres has six bedrooms, six full bathrooms and two half bathrooms, balconies, a pool, an outdoor kitchen and a four-car garage. It has been on Zillow for 284 days.
Closing out the top five is a 20.85-acre waterfront estate on a private lane in Greens Farms, 4 Sherwood Island Lane, listed at $10,500,000 after a $4.5 million price cut on Aug. 3. One family has owned it for more than 65 years, according to the listing, and it looks across Sherwood Island State Park and the Sound, surrounded by protected open space. The 1940 house has 6,215 square feet, seven bedrooms, six full bathrooms and one half bathroom. It has been on Zillow for 214 days.
Prices, listing status and days on market are from each property's Zillow.com listing as of Oct. 26, 2026, and may change. Only homes marked "For sale" or offered as new construction were included; pending, coming-soon, land-only and multifamily listings were left out.
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