Cheshire Homes Command $1.63 Million in South End Market

A contemporary Colonial at 644 S. Brooksvale Road in Cheshire, Connecticut, currently asks $1,630,000 for 6,361 square feet of living space. The property, built in 1987 on 2.26 acres, sits behind the road and includes five bedrooms and four and a half bathrooms. Realtors describe the home as offering a rare blend of privacy, elegance, craftsmanship, and resort-style living. It has been listed on Zillow for 36 days.

The market for high-end housing in South Cheshire features several large properties that have remained on the market for weeks. The current top five listings include four established Colonials and one new construction project. All four established homes are priced above $1.2 million and are located on South Brooksvale Road or Mountaincrest Drive. These listings reflect specific square footage, bedroom counts, and lot sizes that distinguish them from the rest of the local inventory.

At 16 Mountaincrest Drive, a custom Colonial built in 1994 lists for $1,590,000. The 5,021-square-foot home sits on 1.9 acres of park-like grounds with Bethany Mountain in the background. Zillow data indicates five bedrooms, four full bathrooms, and one half bathroom, though the description notes it can function as a four- or five-bedroom residence. This property has been on the market for 40 days.

The neighbor at 1 Mountaincrest Drive, a 1991 Colonial, asks $1,375,000. The 3,718-square-foot home, which the description states is more than 4,000 square feet, sits on 1.84 acres. It features a kitchen with a Sub-Zero refrigerator, a five-burner gas stove, and a granite island that seats five. The living room includes a gas fireplace. This listing has been active for 24 days.

At 885 S. Brooksvale Road, a 1986 custom Colonial on a 2.37-acre corner lot lists for $1,279,000. The seller reduced the price by $100,000 on October 1. The 3,948-square-foot house includes skylights, custom millwork, and a remodeled kitchen with a large island. It has been on Zillow for 59 days, the longest duration among the established homes in the top five.

The fifth property is a new Colonial to be built at 140 Willow St., listed at $899,900. The 2,792-square-foot plan on 0.83 acres features four bedrooms, two full bathrooms, and one half bathroom with an open layout. This new construction listing has been on the market for 236 days. Prices and listing status for all properties are based on Zillow.com data as of October 26, 2026, and include only homes marked for sale or new construction.