CHESTER, CT — Chester's two most expensive homes for sale both date to around 1800, and the priciest comes with 285 feet of Connecticut River frontage, according to listings on Zillow.com.
No. 1 on the list is 288 Middlesex Ave., a waterfront compound the listing calls East View, listed at $2,995,000. Just over a mile from the village, the 2.65-acre property has deep-water access, a six-pile dock with two slips and a 16-ton lift, and a floating dock for paddling. Zillow dates the house to 1800 and lists 4,926 square feet, four bedrooms, four full bathrooms and two half bathrooms. It has been on Zillow for 61 days.
Just behind it is 47 East Kings Highway, which the listing calls the Johnathan Warner house, later known as the Warner-Brooks House, listed at $1,900,000. The listing says Warner built the Federal-style house in 1798, that it is on the National Register of Historic Places and that the original bills, receipts and construction records from its building still survive. It has 3,957 square feet, four bedrooms, three full bathrooms and one half bathroom on 3.2 acres, and has been on Zillow for 44 days.
Rounding out the top three is 7 Hickory Hill Drive, a recently updated 1984 Colonial in the heart of downtown, listed at $775,000. The 3,002-square-foot house has three bedrooms, two full bathrooms and one half bathroom on 1.27 acres, set privately but within walking distance of the village's shops, restaurants and galleries, according to the listing. It has been on Zillow for four days.
No. 4 is 13 High Field Lane, a 1996 custom Colonial at the end of a cul-de-sac minutes from Chester Village, listed at $764,900. Kept by its original owners, the 2,662-square-foot house has four bedrooms, two full bathrooms and one half bathroom on 2.24 acres, with a covered front porch. It has been on Zillow for 50 days.
Closing out the top five is 275 West Main St., a renovated 1971 house on 2 acres across from Cockaponset State Forest, about 3 miles from Chester Village and Cedar Lake, listed at $715,000. The 2,706-square-foot home has four bedrooms, three full bathrooms and one half bathroom, multiple fireplaces and a new kitchen with quartz counters and THOR Gordon Ramsay Collection appliances. It has been on Zillow for 14 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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