Cheshire Housing Market: Five Top-End Homes Now Available
The five most expensive residences currently listed for sale in Cheshire, Connecticut, range in price from $899,900 to $1,630,000.
By Petra Garnier ·
Potential buyers in Cheshire, Connecticut, face a top tier of residential options priced between $899,900 and $1,630,000. As of October 26, 2026, five properties occupy the highest price points on the local market. Four of these homes are existing Colonials located in South Cheshire, while the fifth is a new construction project.
The highest-priced listing is 644 S. Brooksvale Road, asking for $1,630,000. Built in 1987, this contemporary Colonial covers 6,361 square feet on 2.26 acres. The residence features five bedrooms, four full bathrooms, and one half bath. Realtors note that the property offers views of Cheshire Land Trust property and includes a two-story foyer with floor-to-ceiling windows. The home has been listed on Zillow for 36 days.
At $1,590,000, 16 Mountaincrest Drive sits second on the list. This 1994 custom Colonial spans 5,021 square feet on 1.9 acres of park-like grounds. Zillow data indicates five bedrooms, four full bathrooms, and one half bath, though the listing description allows for a four- or five-bedroom configuration. The home has been on the market for 40 days.
The third entry is 1 Mountaincrest Drive, priced at $1,375,000. Built in 1991, this contemporary Colonial occupies 1.84 acres. Zillow lists the size as 3,718 square feet, while the property description cites over 4,000 square feet. The kitchen includes a Sub-Zero refrigerator, a five-burner gas stove, and a granite island. The living room contains a gas fireplace. This home has been listed for 24 days.
885 S. Brooksvale Road ranks fourth at $1,279,000. The seller reduced the price by $100,000 on October 1. Built in 1986, this 3,948-square-foot custom Colonial sits on a 2.37-acre corner lot. It features five bedrooms, four full bathrooms, and one half bath, along with skylights and custom millwork. The property has been on the market for 59 days.
The final entry is a new Colonial at 140 Willow Street, listed for $899,900. The 2,792-square-foot plan is situated on a 0.83-acre lot. It includes four bedrooms, two full bathrooms, and one half bath with an open layout. This property has been on Zillow for 236 days. All prices and days on market reflect data from Zillow as of October 26, 2026.
Source: Patch Doylestown
