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

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
15 Hickory Hill Drive
Chester, CT $875,000

15 Hickory Hill Drive

Chester, CT

$875,000
  • 3 Beds
  • 2/1 Baths
  • 3,233 Sqft
13 High Field Lane
Chester, CT $764,900

13 High Field Lane

Chester, CT

$764,900
  • 4 Beds
  • 2/1 Baths
  • 2,662 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
189 Middlesex Avenue
Chester, CT $3,300,000

189 Middlesex Avenue

Chester, CT

$3,300,000
  • 21,905 Sqft
288 Middlesex Avenue
Chester, CT $2,995,000

288 Middlesex Avenue

Chester, CT

$2,995,000
  • 4 Beds
  • 4/2 Baths
  • 4,926 Sqft
59-65 Maple Street
Chester, CT $1,995,000

59-65 Maple Street

Chester, CT

$1,995,000
  • 7 Beds
  • 7 Baths
  • 8,500 Sqft

Chester

Area Map

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Chester

Market Snapshot

Units Sold

September 2026

4 TOTAL UNITS

image description +100.0% image description +0.0% vs

Median Sales Price

September 2026 - Single Family Homes

$500K
image description -21.9% image description +23.5% vs

Percentage of Asking Price

September 2026 Single Family Homes

106%
image description +6.9% image description +5.2% vs
106%
image description +6.9% image description +5.2% vs
106%
image description +6.9% image description +5.2% vs