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.

Read MoreRead Less

Featured Listings

31 Parkers Point Road
Chester, CT $3,495,000

31 Parkers Point Road

Chester, CT

$3,495,000
  • 3 Beds
  • 3/1 Baths
  • 4,727 Sqft
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
25 Gilbert Hill Road
Chester, CT $1,100,000

25 Gilbert Hill Road

Chester, CT

$1,100,000
  • 4 Beds
  • 4/1 Baths
  • 3,351 Sqft
132 Main Street
Chester, CT $975,000

132 Main Street

Chester, CT

$975,000
  • 23,467 Sqft
25 Spring Street
Chester, CT $895,000

25 Spring Street

Chester, CT

$895,000
  • 3 Beds
  • 2/1 Baths
  • 2,164 Sqft
43 North Main Street
Chester, CT $784,900

43 North Main Street

Chester, CT

$784,900
  • 3 Beds
  • 1/1 Baths
  • 1,538 Sqft
42 West Main Street
Chester, CT $650,000

42 West Main Street

Chester, CT

$650,000
  • 4 Beds
  • 2 Baths
  • 1,766 Sqft
6 Pleasant Street  #2
Chester, CT $1,750/mo

6 Pleasant Street #2

Chester, CT

$1,750/mo
  • 2 Beds
  • 1 Baths
  • 800 Sqft

Chester

Area Map

Loading...

Chester

Market Snapshot

Units Sold

April 2025

4 TOTAL UNITS

image description +100.0% image description +300.0% vs

Median Sales Price

April 2025 - Single Family Homes

$663K
image description -14.5% image description +110.3% vs

Percentage of Asking Price

April 2025 Single Family Homes

99%
image description +21.7% image description +1.7% vs
99%
image description +21.7% image description +1.7% vs