Chester

Shoreline, Connecticut

VIEW 24 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

132 Main Street
Chester, CT $975,000

132 Main Street

Chester, CT

$975,000
  • 23,467 Sqft
9 Hickory Hill Drive
Chester, CT $799,000

9 Hickory Hill Drive

Chester, CT

$799,000
  • 3 Beds
  • 2/1 Baths
  • 2,888 Sqft
8 Butter Jones Road
Chester, CT $775,000

8 Butter Jones Road

Chester, CT

$775,000
  • 3 Beds
  • 2/1 Baths
  • 2,139 Sqft
6 - 8 W Main Street
Chester, CT $725,000

6 - 8 W Main Street

Chester, CT

$725,000
  • 4 Beds
  • 2 Baths
  • 2,160 Sqft
55 Liberty Street
Chester, CT $2,500/mo

55 Liberty Street

Chester, CT

$2,500/mo
  • 2 Beds
  • 2/1 Baths
  • 1,328 Sqft
159 Main Street #E
Chester, CT $2,100/mo

159 Main Street #E

Chester, CT

$2,100/mo
  • 2 Beds
  • 1 Baths
  • 790 Sqft
189 Middlesex Avenue
Chester, CT $4,695,000

189 Middlesex Avenue

Chester, CT

$4,695,000
  • 21,905 Sqft
288 Middlesex Avenue
Chester, CT $3,375,000

288 Middlesex Avenue

Chester, CT

$3,375,000
  • 4 Beds
  • 4/2 Baths
  • 4,926 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 2025

6 TOTAL UNITS

image description +100.0% image description +200.0% since

Median Sales Price

November 2025 - Single Family Homes

$758K
image description +76.2% image description -67.1% since

Percentage of Asking Price

November 2025 Single Family Homes

92%
image description -14.9% image description +8.3% since
92%
image description -14.9% image description +8.3% since