Take A Tour: Guilford's Five Priciest Homes On The Market Right Now

GUILFORD, CT — Sachem's Head dominates Guilford's most expensive homes for sale, and the top listing is in a class by itself: a $35 million waterfront compound with three docks, a vineyard and its own go-kart track. It's priced at about six times the next listing on Zillow.com.

No. 1 on the list is 215 Uncas Point Road, three combined properties on 13.03 acres with 1,900 feet of waterfront, listed at $35,000,000. Along with the 2009 main house, which has six bedrooms, four full bathrooms and one half bathroom, the compound includes a three-bedroom guest house, a one-bedroom in-law apartment and a carriage house. Outside are three docks, a boat lift, a vineyard, orchards, a pool, a spa, an outdoor kitchen, a tennis and basketball court and a go-kart track. Zillow lists the main house at 5,354 square feet; the description says about 5,534. It has been on Zillow for 821 days.

Just behind it is a modern Mediterranean house high on 4.31 acres at 345 Vineyard Point Road, also in Sachem's Head, at $5,750,000. The 8,070-square-foot home has four bedrooms, six full bathrooms and two half bathrooms, panoramic views of Long Island Sound, Palm Beach-inspired finishes, a floating stairway and a main-floor primary suite. Zillow dates it to 2010, while the description says 2012. It has been on Zillow for 18 days.

Rounding out the top three is a new condo at Eagleview at Guilford, unit 2 at 405 Whitfield St., listed at $3,995,000. The unit has 6,216 square feet, expandable to more than 8,000, with six bedrooms, four full bathrooms and two half bathrooms, a private balcony and views of salt marshes and the Sound. It has been on Zillow for 350 days.

No. 4 is 57 Faulkner Drive, a 2005 custom home with water views from every room, listed at $2,999,000 after a $301,000 price cut on Sept. 15. The 2,891-square-foot house has three bedrooms, two full bathrooms and one half bathroom and radiant-heated floors on all three levels. The sale covers three deeds totaling about 2 acres, including two waterfront lots, one of them a spot for a future dock. It has been on Zillow for 135 days.

Closing out the top five is a gated, wooded waterfront property at 76 Sachem Head Road, listed at $2,650,000 after a $150,000 price cut on Aug. 18. Built in 2004, the 5,620-square-foot house has four bedrooms, four full bathrooms and one half bathroom on 2.31 acres, a living room with a custom mural and an aquarium, a home theater and a sauna. It has been on Zillow for 129 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.