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

Goose 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.
Goose Hill Road
$145,000
  • 4.91 acres

132 Main Street

Chester, CT

132 Main Street Under Contract
$975,000
  • 23,467 sqft
  • 1.94 acres
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59-61 Wig Hill Road

Chester, CT

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

3 Inspiration Lane #1

Chester, CT

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

21 Main Street

Chester, CT

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

Turkey Hill Road

Chester, CT

Turkey Hill Road
$99,900
  • 1 acres

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 Open House
$525,000
  • 3 bed
  • 2 bath
  • 1,188 sqft
  • 0.68 acres

Open House: Sunday, Jun 21, 12:00pm - 2:00pm

3 Kirtland Avenue

Chester, CT

3 Kirtland Avenue
$282,225
  • 2 bed
  • 2 bath
  • 1,344 sqft
  • 0.33 acres

136 Goose Hill Road

Chester, CT

136 Goose Hill Road
$945,000
  • 4 bed
  • 3 bath
  • 3,343 sqft
  • 2.05 acres

47 East Kings Highway

Chester, CT

47 East Kings Highway New to Market
$2,200,000
  • 4 bed
  • 3/1 bath
  • 3,957 sqft
  • 3.2 acres

Chester Real Estate Market

Single Family Homes
May 2026
May 2025
Chester, CT Average Days on Market
May 2026 5
May 2025 13 -61.0%
Median Sales Price homes in Chester
May 2026 $695K
May 2025 $613K +13.3%
Chester, CT Average Price per Square Foot
May 2026 $342
May 2025 $265 +28.8%
Total Single Family Homes Sold in Chester, CT
May 2026 1
May 2025 6 -83.3%

Chester is within Shoreline, Connecticut

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