Chester, CT Real Estate & Homes for Sale

18 Listings Found:
  • Area Chester
  • Price
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10 Denlar Drive

Chester, CT

10 Denlar Drive
$1,450,000
  • 28,525 sqft
  • 2.88 acres

55 Liberty Street

Chester, CT

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

59-61 Wig Hill Road

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.
59-61 Wig Hill Road
$695,000
  • 5 bed
  • 2/1 bath
  • 3,862 sqft
  • 3.64 acres

132 Main Street

Chester, CT

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

21 Winthrop Road

Chester, CT

21 Winthrop Road Under Contract
$2,400/mo
  • 2 bed
  • 1/1 bath
  • 1,260 sqft
  • 2.81 acres

11 Kings Highway

Chester, CT

11 Kings Highway
$238,500
  • 1.5 acres

3 Inspiration Lane #1

Chester, CT

3 Inspiration Lane #1
$5,500/mo
  • 4,000 sqft
  • 8.37 acres

189 Middlesex Avenue

Chester, CT

189 Middlesex Avenue
$4,200,000
  • 21,905 sqft
  • 3.02 acres
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21 Main Street

Chester, CT

21 Main Street
$1,200,000
  • 3,000 sqft

288 Middlesex Avenue

Chester, CT

288 Middlesex Avenue
$3,150,000
  • 4 bed
  • 4/2 bath
  • 4,926 sqft
  • 2.65 acres

59-65 Maple Street

Chester, CT

59-65 Maple Street
$2,100,000
  • 11 bed
  • 10/2 bath
  • 8,500 sqft
  • 2.56 acres

135 Middlesex Avenue

Chester, CT

135 Middlesex Avenue New to Market
$525,000
  • 3 bed
  • 2 bath
  • 1,188 sqft
  • 0.68 acres

64-68 Middlesex Avenue

Chester, CT

64-68 Middlesex Avenue New to Market
$2,600/mo
  • 3 bed
  • 1/1 bath
  • 1,337 sqft
  • 0.73 acres

184 Middlesex Avenue #6

Chester, CT

184 Middlesex Avenue #6 New to Market
$1,500/mo
  • 1 bath
  • 4,060 sqft
  • 1.19 acres

Chester Real Estate Market

Single Family Homes
April 2026
April 2025
Chester, CT Average Days on Market
April 2026 67
April 2025 38 +78.7%
Median Sales Price homes in Chester
April 2026 $523K
April 2025 $663K -21.1%
Chester, CT Average Price per Square Foot
April 2026 $303
April 2025 $292 +3.8%
Total Single Family Homes Sold in Chester, CT
April 2026 4
April 2025 4 +0.0%

Chester is within Shoreline, Connecticut

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