Chester, CT Real Estate & Homes for Sale

16 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

132 Main Street

Chester, CT

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

6 Pelton Hill

Chester, CT

6 Pelton Hill Coming Soon
$738,500
  • 3 bed
  • 1/1 bath
  • 1,982 sqft
  • 2.3 acres

Be the first to know: On Market Mar 27

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

43 Bokum Road

Chester, CT

43 Bokum Road
$200,000
  • 2.25 acres

189 Middlesex Avenue

Chester, CT

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

15 Liberty Street

Chester, CT

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

79 Middlesex Avenue

Chester, CT

79 Middlesex Avenue
$448,900
  • 2 bed
  • 1 bath
  • 1,470 sqft
  • 0.82 acres

21 Main Street

Chester, CT

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

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1 Ferry Road

Chester, CT

1 Ferry Road
$650,000
  • 3 bed
  • 3 bath
  • 2,752 sqft
  • 1.39 acres

26 Ferry Road

Chester, CT

26 Ferry Road
$850,000
  • 4 bed
  • 2 bath
  • 8,382 sqft
  • 2.09 acres

96 West Main Street

Chester, CT

96 West Main Street New to Market
$2,200/mo
  • 2 bed
  • 1 bath
  • 1,100 sqft
  • 0.27 acres

98 West Main Street

Chester, CT

98 West Main Street New to Market
$2,700/mo
  • 3 bed
  • 1 bath
  • 1,200 sqft
  • 0.27 acres

Chester Real Estate Market

Single Family Homes
February 2026
February 2025
Chester, CT Average Days on Market
February 2026 62
February 2025 5 +1,133.3%
Median Sales Price homes in Chester
February 2026 $530K
February 2025 $360K +47.2%
Chester, CT Average Price per Square Foot
February 2026 $258
February 2025 $288 -10.5%
Total Single Family Homes Sold in Chester, CT
February 2026 3
February 2025 1 +200.0%

Chester is within Shoreline, Connecticut

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