Cheshire's 5 Priciest Homes On The Market Right Now

CHESHIRE, CT — Four South Cheshire Colonials, two of them on South Brooksvale Road and two on Mountaincrest Drive, lead the list of Cheshire's most expensive homes for sale on Zillow.com. All four are priced above $1.2 million.

No. 1 on the list is 644 S. Brooksvale Road, a contemporary Colonial set well back from the road on 2.26 acres, asking $1,630,000. Built in 1987, the 6,361-square-foot house has five bedrooms, four full bathrooms and one half bathroom, views of Cheshire Land Trust property and a two-story foyer with floor-to-ceiling windows. It has been on Zillow for 36 days.

Just behind it is 16 Mountaincrest Drive, a custom Colonial high above South Cheshire with Bethany Mountain as a backdrop, listed at $1,590,000. Built in 1994, the 5,021-square-foot house sits on 1.9 acres of park-like grounds. Zillow lists five bedrooms, four full bathrooms and one half bathroom; the description calls it a four- or five-bedroom home. It has been on Zillow for 40 days.

Rounding out the top three is its neighbor at 1 Mountaincrest Drive, a 1991 contemporary Colonial on a hill, at $1,375,000. It has four bedrooms, four full bathrooms and one half bathroom on 1.84 acres. Zillow lists 3,718 square feet, while the description says more than 4,000. The kitchen has a Sub-Zero refrigerator, a five-burner gas stove and a granite island that seats five, and the living room has a gas fireplace. It has been on Zillow for 24 days.

No. 4 is 885 S. Brooksvale Road, a custom Colonial on a 2.37-acre corner lot behind wrought iron gates, listed at $1,279,000 after a $100,000 price cut on Oct. 1. Built in 1986, the 3,948-square-foot house has five bedrooms, four full bathrooms and one half bathroom, skylights, custom millwork and a remodeled kitchen with a large island. It has been on Zillow for 59 days.

Closing out the top five is a new Colonial to be built on a secluded rear lot at 140 Willow St., listed at $899,900. The 2,792-square-foot plan on 0.83 acres has four bedrooms, two full bathrooms and one half bathroom and an open layout. It has been on Zillow for 236 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.