Chester

Shoreline, Connecticut

VIEW 17 COMMUNITY LISTINGS

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

96 Middlesex Avenue
Chester, CT $1,375,000

96 Middlesex Avenue

Chester, CT

$1,375,000
  • 4 Beds
  • 3/1 Baths
  • 3,153 Sqft
132 Main Street
Chester, CT $975,000

132 Main Street

Chester, CT

$975,000
  • 23,467 Sqft
5 Marina View Drive
Chester, CT $545,000

5 Marina View Drive

Chester, CT

$545,000
  • 3 Beds
  • 3/1 Baths
  • 2,037 Sqft
2 Sypher Road
Chester, CT $446,000

2 Sypher Road

Chester, CT

$446,000
  • 4 Beds
  • 2/1 Baths
  • 2,278 Sqft
5 Bates Lane
Chester, CT $2,700/mo

5 Bates Lane

Chester, CT

$2,700/mo
  • 2 Beds
  • 2 Baths
  • 1,346 Sqft
191 Middlesex Avenue
Chester, CT $2,200/mo

191 Middlesex Avenue

Chester, CT

$2,200/mo
  • 1 Beds
  • 1 Baths
  • 750 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
19 West Main Street
Chester, CT $1,499,000

19 West Main Street

Chester, CT

$1,499,000
  • 4 Beds
  • 3/1 Baths
  • 4,205 Sqft

Chester

Area Map

Chester is within Shoreline, Connecticut and borders Deep River, East Haddam, Killingworth and Lyme.

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Featured Communities Within

Shoreline

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Chester

Market Snapshot

Units Sold

November 2024

3 TOTAL UNITS

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Median Sales Price

November 2024 - Single Family Homes

$430K
image description -81.3% image description -32.0% since

Percentage of Asking Price

November 2024 Single Family Homes

108%
image description +27.2% image description -13.5% since
108%
image description +27.2% image description -13.5% since