Chester

Shoreline, Connecticut

VIEW 16 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

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
9 Hickory Hill Drive
Chester, CT $779,000

9 Hickory Hill Drive

Chester, CT

$779,000
  • 3 Beds
  • 2/1 Baths
  • 2,888 Sqft
8 Butter Jones Road
Chester, CT $745,000

8 Butter Jones Road

Chester, CT

$745,000
  • 3 Beds
  • 2/1 Baths
  • 2,139 Sqft
189 Middlesex Avenue
Chester, CT $4,695,000

189 Middlesex Avenue

Chester, CT

$4,695,000
  • 21,905 Sqft
21 Main Street
Chester, CT $1,200,000

21 Main Street

Chester, CT

$1,200,000
  • 3,000 Sqft
26 Ferry Road
Chester, CT $850,000

26 Ferry Road

Chester, CT

$850,000
  • 4 Beds
  • 2 Baths
  • 8,382 Sqft
1 Ferry Road
Chester, CT $685,000

1 Ferry Road

Chester, CT

$685,000
  • 3 Beds
  • 3 Baths
  • 2,752 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

January 2026

2 TOTAL UNITS

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Median Sales Price

January 2026 - Single Family Homes

$550K
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Percentage of Asking Price

January 2026 Single Family Homes

98%
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98%
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