MADISON, CT — The most expensive home for sale in Madison is really about the land: 16 acres along the Hammonasset River, the last piece of a farm one family has owned for 200 years. It leads the town's five priciest listings on Zillow.com, three of which come with beach access.
No. 1 on the list is 118 River Road, asking $5,000,000. The listing says the 15.9-acre property, with more than 1,500 feet along the Hammonasset River, is the last piece of the original farm to be sold, with open hay fields, tidal marshes and river views. The 1958 house has 3,109 square feet, three bedrooms and three full bathrooms. It has been on Zillow for 60 days.
Just behind it is a new home to be built with beach rights at 22 Stone Road, listed at $3,200,000. The 4,937-square-foot plan on an acre has five bedrooms, three full bathrooms and one half bathroom, ceilings above 9 feet, red oak floors and a kitchen with Sub-Zero, Wolf and Bosch appliances and a butler's pantry. It has been on Zillow for 56 days.
Rounding out the top three is 45 Island Ave., less than a tenth of a mile from the town green and the beaches, listed at $3,000,000 after a $495,000 price cut on Sept. 14. The 2001 house, completely reimagined since, has 5,657 square feet, five bedrooms, four full bathrooms and two half bathrooms on 1.57 secluded acres, with private beach access, a walk-out guest suite and a three-car garage. It has been on Zillow for 196 days.
No. 4 is a 10-room Colonial in the Barberry Farms beach community, 17 Barberry Lane, at $2,700,000 after a $300,000 price cut on Sept. 22. The listing says homes there rarely come up for sale, with only two MLS sales since 2021, and residents share a wide sandy beach with storage for kayaks and small sailboats. The 1955 house has 4,833 square feet, four bedrooms, four full bathrooms and two half bathrooms. It has been on Zillow for 73 days.
Closing out the top five is 24 Indigo Trail, a 2003 English Georgian house on 5.65 wooded acres with a stream and the stone remains of a historic mill, listed at $2,550,000 after a $100,000 price cut on Sept. 21. The 6,194-square-foot home has four bedrooms, four full bathrooms and one half bathroom. It has been on Zillow for 202 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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