Chester

Chester, incorporated in 1836, is a small, former mill town with roots in the shipbuilding industry.

Located on the hillside of the Connecticut River, Chester achieved fame as a center for inventors and manufacturing innovations. A town for all seasons, Chester reflects typical New England charm with its rolling hills, pristine lakes, rushing waterfalls, lush forests and sparkling streams and ponds. The town is a haven for nature lovers, who will find a variety of flora, fauna and wildlife throughout Cockaponset State Park and along the Connecticut River. Because Chester’s geography includes a healthy assortment of natural water features, many property owners take advantage of their natural surroundings – streams, waterfalls and ponds – by incorporating them into their landscaping. Chester has a vibrant downtown hub, lined with an array of eateries, retail shops and businesses. It is home to the 65-foot-long Chester-Hadlyme Ferry, owned and operated by the State of Connecticut. The ferry operates seasonally and has a capacity for approximately 50 passengers and eight to nine vehicles.

Located on the hillside of the Connecticut River, Chester achieved fame as a center for inventors and manufacturing innovations. A town for all seasons, Chester reflects typical New England charm with its rolling hills, pristine lakes, rushing waterfalls, lush forests and sparkling streams and ponds. The town is a haven for nature lovers, who will find a variety of flora, fauna and wildlife throughout Cockaponset State Park and along the Connecticut River. Because Chester’s geography includes a healthy assortment of natural water features, many property owners take advantage of their natural surroundings – streams, waterfalls and ponds – by incorporating them into their landscaping. Chester has a vibrant downtown hub, lined with an array of eateries, retail shops and businesses. It is home to the 65-foot-long Chester-Hadlyme Ferry, owned and operated by the State of Connecticut. The ferry operates seasonally and has a capacity for approximately 50 passengers and eight to nine vehicles.

Located on the hillside of the Connecticut River, Chester achieved fame as a center for inventors and manufacturing innovations. A town for all seasons, Chester reflects typical New England charm with its rolling hills, pristine lakes, rushing waterfalls, lush forests and sparkling streams and ponds. The town is a haven for nature lovers, who will find a variety of flora, fauna and wildlife throughout Cockaponset State Park and along the Connecticut River. Because Chester’s geography includes a healthy assortment of natural water features, many property owners take advantage of their natural surroundings – streams, waterfalls and ponds – by incorporating them into their landscaping. Chester has a vibrant downtown hub, lined with an array of eateries, retail shops and businesses. It is home to the 65-foot-long Chester-Hadlyme Ferry, owned and operated by the State of Connecticut. The ferry operates seasonally and has a capacity for approximately 50 passengers and eight to nine vehicles.

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Featured Listings

10 Denlar Drive
Chester, CT $1,450,000

10 Denlar Drive

Chester, CT

$1,450,000
  • 28,525 Sqft
132 Main Street
Chester, CT $975,000

132 Main Street

Chester, CT

$975,000
  • 23,467 Sqft
59-61 Wig Hill Road
Chester, CT $695,000

59-61 Wig Hill Road

Chester, CT

$695,000
  • 5 Beds
  • 2/1 Baths
  • 3,862 Sqft
21 Winthrop Road
Chester, CT $2,400/mo

21 Winthrop Road

Chester, CT

$2,400/mo
  • 2 Beds
  • 1/1 Baths
  • 1,260 Sqft
189 Middlesex Avenue
Chester, CT $4,200,000

189 Middlesex Avenue

Chester, CT

$4,200,000
  • 21,905 Sqft
288 Middlesex Avenue
Chester, CT $3,150,000

288 Middlesex Avenue

Chester, CT

$3,150,000
  • 4 Beds
  • 4/2 Baths
  • 4,926 Sqft
59-65 Maple Street
Chester, CT $2,100,000

59-65 Maple Street

Chester, CT

$2,100,000
  • 11 Beds
  • 10/2 Baths
  • 8,500 Sqft
21 Main Street
Chester, CT $1,200,000

21 Main Street

Chester, CT

$1,200,000
  • 3,000 Sqft

Chester

Area Map

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Chester

Market Snapshot

Units Sold

March 2026

2 TOTAL UNITS

image description -33.3% image description -33.3% vs

Median Sales Price

March 2026 - Single Family Homes

$632K
image description +17.0% image description +85.9% vs

Percentage of Asking Price

March 2026 Single Family Homes

98%
image description -5.5% image description +0.9% vs
98%
image description -5.5% image description +0.9% vs