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Chester

A Vibrant Town Full of Creative People 

Discover this Middlesex town that celebrates community, cuisine, conversation, the Arts and the outdoors.

Homes for Sale in Chester

Homes for Rent in Chester

Chester

Settled by Europeans in 1692, Chester thrived as a shipbuilding and mill town. It is home to the Chester Fife & Drum Corps which has been continuously active since 1868, making it one of the oldest in the entire United States.


Ideally situated in the Connecticut River Valley, Chester boasts thousands of acres of state forest with hiking trails, as well as a number of marinas for boating enthusiasts.


Chester simultaneously cherishes its historical, small-town way of life and embraces life in the 21st century with superior restaurants, elegant shops and numerous art galleries.

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Median Sale Price

$695k

13.30 % Since May 2025

Average Days on Market

5
-58.30 % Since May 2025

Properties for Sale in Chester

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  • 7 Properties
  • Page 1 of 1
$3,150,000
Active
288 Middlesex Avenue
Chester, CT 06412
  • 4 Beds
  • 6 Baths
  • 4926 sq.ft.
  • 2.65 Acres
$2,200,000
Active
47 East Kings Highway
Chester, CT 06412
  • 4 Beds
  • 4 Baths
  • 3957 sq.ft.
  • 3.2 Acres
$945,000
Active
136 Goose Hill Road
Chester, CT 06412
  • 4 Beds
  • 3 Baths
  • 3343 sq.ft.
  • 2.05 Acres
$525,000
Active
12 Meadow Lane
Chester, CT 06412
  • 3 Beds
  • 3 Baths
  • 2971 sq.ft.
  • 4.15 Acres
$525,000
Active
135 Middlesex Avenue
Chester, CT 06412
  • 3 Beds
  • 2 Baths
  • 1188 sq.ft.
  • 0.68 Acres
$324,900
Active
92 Water Street
Chester, CT 06412
  • 3 Beds
  • 1 Baths
  • 1217 sq.ft.
  • 0.27 Acres
$299,900
Active
90 Water Street
Chester, CT 06412
  • 1 Beds
  • 1 Baths
  • 1034 sq.ft.
  • 0.28 Acres
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  • 7 Properties
  • Page 1 of 1