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 $1,299,000

7 Old Depot Road

Chester, CT

$1,299,000
  • 4 Beds
  • 2/1 Baths
  • 3,149 Sqft
16 Waterhouse Lane
Chester, CT $1,250,000

16 Waterhouse Lane

Chester, CT

$1,250,000
  • 4 Beds
  • 4/1 Baths
  • 4,661 Sqft
132 Main Street
Chester, CT $975,000

132 Main Street

Chester, CT

$975,000
  • 23,467 Sqft
6 Old County Road
Chester, CT $869,000

6 Old County Road

Chester, CT

$869,000
  • 4 Beds
  • 2/1 Baths
  • 2,680 Sqft
10 Old County Road
Chester, CT $839,623

10 Old County Road

Chester, CT

$839,623
  • 4 Beds
  • 3/1 Baths
  • 2,755 Sqft
42 West Main Street
Chester, CT $699,990

42 West Main Street

Chester, CT

$699,990
  • 4 Beds
  • 2 Baths
  • 1,766 Sqft
159 Main Street  #B
Chester, CT $1,850/mo

159 Main Street #B

Chester, CT

$1,850/mo
  • 2 Beds
  • 1 Baths
  • 750 Sqft
6 Pleasant Street  #3
Chester, CT $1,600/mo

6 Pleasant Street #3

Chester, CT

$1,600/mo
  • 2 Beds
  • 1 Baths
  • 800 Sqft

Chester

Area Map

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Chester

Market Snapshot

Units Sold

February 2025

1 TOTAL UNITS

image description +0.0% image description -66.7% vs

Median Sales Price

February 2025 - Single Family Homes

$360K
image description -20.0% vs

Percentage of Asking Price

February 2025 Single Family Homes

113%
image description +13.0% vs
113%
image description +13.0% vs