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

7 Old Depot Road
Chester, CT $1,150,000

7 Old Depot Road

Chester, CT

$1,150,000
  • 4 Beds
  • 2/1 Baths
  • 3,149 Sqft
132 Main Street
Chester, CT $975,000

132 Main Street

Chester, CT

$975,000
  • 23,467 Sqft
137 Main Street
Chester, CT $600,000

137 Main Street

Chester, CT

$600,000
  • 3 Beds
  • 1/1 Baths
  • 1,570 Sqft
189 Middlesex Avenue
Chester, CT $5,285,000

189 Middlesex Avenue

Chester, CT

$5,285,000
  • 21,905 Sqft
33 Liberty Street
Chester, CT $1,500,000

33 Liberty Street

Chester, CT

$1,500,000
  • 26,142 Sqft
32 Gilbert Hill Road
Chester, CT $995,000

32 Gilbert Hill Road

Chester, CT

$995,000
  • 3 Beds
  • 3 Baths
  • 3,788 Sqft
88 Winthrop Road
Chester, CT $985,000

88 Winthrop Road

Chester, CT

$985,000
  • 33.97 Acres
88 Winthrop Road
Chester, CT $985,000

88 Winthrop Road

Chester, CT

$985,000
  • 2 Beds
  • 2/1 Baths
  • 2,240 Sqft

Chester

Area Map

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Chester

Market Snapshot

Units Sold

June 2025

3 TOTAL UNITS

image description -25.0% image description -50.0% vs

Median Sales Price

June 2025 - Single Family Homes

$1.1M
image description +142.8% image description +128.1% vs

Percentage of Asking Price

June 2025 Single Family Homes

97%
image description -3.4% image description -4.6% vs
97%
image description -3.4% image description -4.6% vs