Chester, CT Real Estate & Homes for Sale

21 Listings Found:
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      7 Old Depot Road

      Chester, CT

      7 Old Depot Road
      $1,299,000
      • 4 bed
      • 2/1 bath
      • 3,149 sqft
      • 6.08 acres

      6 Pleasant Street #2

      Chester, CT

      6 Pleasant Street #2 New to Market
      $1,750/mo
      • 2 bed
      • 1 bath
      • 800 sqft
      • 0.41 acres

      42 West Main Street

      Chester, CT

      42 West Main Street New to Market
      $650,000
      • 4 bed
      • 2 bath
      • 1,766 sqft
      • 1.1 acres

      132 Main Street

      Chester, CT

      132 Main Street Under Contract
      $975,000
      • 23,467 sqft
      • 1.94 acres

      6 Old County Road

      Chester, CT

      6 Old County Road Under Contract
      $869,000
      • 4 bed
      • 2/1 bath
      • 2,680 sqft
      • 2.03 acres

      16 Waterhouse Lane

      Chester, CT

      16 Waterhouse Lane Under Contract
      $1,250,000
      • 4 bed
      • 4/1 bath
      • 4,661 sqft
      • 2.78 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

      28 South Wig Hill Road

      Chester, CT

      28 South Wig Hill Road
      $725,000
      • 2 bed
      • 3 bath
      • 3,091 sqft
      • 2.34 acres

      56 Middlesex Avenue

      Chester, CT

      56 Middlesex Avenue
      $635,000
      • 1 bath
      • 6,348 sqft
      • 0.72 acres
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      189 Middlesex Avenue

      Chester, CT

      189 Middlesex Avenue
      $2,750/mo
      • 1,850 sqft
      • 3.02 acres

      88 Winthrop Road

      Chester, CT

      88 Winthrop Road
      $985,000
      • 2 bed
      • 2/1 bath
      • 2,240 sqft
      • 33.97 acres

      88 Winthrop Road

      Chester, CT

      88 Winthrop Road
      $985,000
      • 33.97 acres

      24 East Liberty Street

      Chester, CT

      24 East Liberty Street New to Market
      $419,000
      • 4 bed
      • 2 bath
      • 1,926 sqft
      • 1.68 acres

      Chester Real Estate Market

      Single Family Homes
      March 2025
      March 2024
      Chester, CT Average Days on Market
      March 2025 75
      March 2024 11 +611.1%
      Median Sales Price homes in Chester
      March 2025 $540K
      March 2024 $340K +58.8%
      Chester, CT Average Price per Square Foot
      March 2025 $272
      March 2024 $205 +32.5%
      Total Single Family Homes Sold in Chester, CT
      March 2025 3
      March 2024 3 +0.0%

      Chester is within Shoreline, Connecticut

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