Chester, CT Real Estate & Homes for Sale

24 Listings Found:
  • Area Chester
  • Price
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55 Liberty Street

Chester, CT

55 Liberty Street
$2,500/mo
  • 2 bed
  • 2/1 bath
  • 1,328 sqft
  • 0.51 acres

8 Butter Jones Road

Chester, CT

8 Butter Jones Road
$775,000
  • 3 bed
  • 2/1 bath
  • 2,139 sqft
  • 2.01 acres

159 Main Street #E

Chester, CT

159 Main Street #E
$2,100/mo
  • 2 bed
  • 1 bath
  • 790 sqft
  • 0.31 acres

6 - 8 W Main Street

Chester, CT

6 - 8 W Main Street
$725,000
  • 4 bed
  • 2 bath
  • 2,160 sqft
  • 0.2 acres

9 Hickory Hill Drive

Chester, CT

9 Hickory Hill Drive
$799,000
  • 3 bed
  • 2/1 bath
  • 2,888 sqft
  • 1.23 acres

132 Main Street

Chester, CT

Contingent The sellers have accepted an offer on the property, however, the offer relies on contingencies yet to be lifted. It may still be possible to tour these properties and submit a backup offer.
132 Main Street
$975,000
  • 23,467 sqft
  • 1.94 acres

11 Kings Highway

Chester, CT

11 Kings Highway
$232,500
  • 1.5 acres

3 Inspiration Lane #5

Chester, CT

3 Inspiration Lane #5
$850/mo
  • 1 bath
  • 800 sqft
  • 8.37 acres

3 Inspiration Lane #1

Chester, CT

3 Inspiration Lane #1
$6,500/mo
  • 4,000 sqft
  • 8.37 acres

43 Bokum Road

Chester, CT

43 Bokum Road
$200,000
  • 2.25 acres
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189 Middlesex Avenue

Chester, CT

189 Middlesex Avenue
$4,695,000
  • 21,905 sqft
  • 3.02 acres

288 Middlesex Avenue

Chester, CT

288 Middlesex Avenue
$3,375,000
  • 4 bed
  • 4/2 bath
  • 4,926 sqft
  • 2.65 acres

15 Liberty Street

Chester, CT

15 Liberty Street
$7,500/mo
  • 4 bed
  • 4/1 bath
  • 4,708 sqft
  • 2.74 acres

60 Goose Hill Road

Chester, CT

60 Goose Hill Road
$849,900
  • 7 bed
  • 2 bath
  • 2,402 sqft
  • 0.56 acres

Chester Real Estate Market

Single Family Homes
November 2025
November 2024
Chester, CT Average Days on Market
November 2025 56
November 2024 10 +440.3%
Median Sales Price homes in Chester
November 2025 $758K
November 2024 $430K +76.2%
Chester, CT Average Price per Square Foot
November 2025 $332
November 2024 $246 +34.7%
Total Single Family Homes Sold in Chester, CT
November 2025 6
November 2024 3 +100.0%

Chester is within Shoreline, Connecticut

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