1,691

Chester, CT Homes

Section Image
    • 230 W Main St, Chester, CT 06412

      Est $402,252

      Not Listed For Sale

      230 W Main St, Chester, CT 06412

      • 2 Beds
      • 1.5 Baths
      • 1,530 Sq Ft
      • Built 1986
      230 W Main St, Chester, CT 06412

      Last Sold Summary

      • 1% Below List Price
      • $265/SF
      • 24 Days On Market
      • Last Sold Price $405,000
      • Sep 30, 2024

      Last Listing Agent Siobhan McLaughlin William Raveis Real Estate

  • /38

    $695,000

    $29K PRICE DROP Under Contract
    • 5 Beds
    • 2.5 Baths
    • 3,862 Sq Ft

    59 Wig Hill Rd, Chester, CT 06412

    The spacious main house and separate guest/rental house sit on 3.64 park like acres abutting Chester Land Trust property. The front to back living/dining room features two large picture windows overlooking the rear landscape and a vaulted ceiling with second floor balcony. The cook's kitchen features newer appliances, granite counters, tile floor and eating area with sliding glass doors to a deck

    Joseph Kelly William Pitt Sotheby's Int'l

    59 Wig Hill Rd, Chester, CT 06412
  • 23 Spring St, Chester, CT 06412

    $550,000

    Sold Oct 15, 2025

    23 Spring St, Chester, CT 06412

    • 2 Beds
    • 1.5 Baths
    • 1,104 Sq Ft
    • Built 1920

    Last Sold Summary

    • 17% Above List Price
    • $498/SF
    • 15 Days On Market

    Current Estimated Value $559,635

    Last Listing Agent Susan Malan William Pitt Sotheby's Int'l

    23 Spring St, Chester, CT 06412
    • 7 Pine Knoll Dr, Chester, CT 06412

      Est $682,321

      Not Listed For Sale

      7 Pine Knoll Dr, Chester, CT 06412

      • 3 Beds
      • 2.5 Baths
      • 2,607 Sq Ft
      • Built 2002
      7 Pine Knoll Dr, Chester, CT 06412

      Last Sold Summary

      • 18% Above List Price
      • $222/SF
      • 4 Days On Market
      • Last Sold Price $580,000
      • Jul 28, 2023

      Last Listing Agent Jamie Franco Coldwell Banker

  • 50 Bokum Rd, Chester, CT 06412

    $375,000

    Sold Nov 13, 2025

    50 Bokum Rd, Chester, CT 06412

    • 2 Beds
    • 1.5 Baths
    • 807 Sq Ft
    • Built 1912

    Last Sold Summary

    • 12% Below List Price
    • $465/SF
    • 59 Days On Market

    Current Estimated Value $377,642

    Last Listing Agent Cynthia Sigurdson William Pitt Sotheby's Int'l

    50 Bokum Rd, Chester, CT 06412
    • 22 Waterhouse Ln, Chester, CT 06412

      Est $885,879

      Not Listed For Sale

      22 Waterhouse Ln, Chester, CT 06412

      • 3 Beds
      • 2.5 Baths
      • 3,802 Sq Ft
      • Built 1999
      22 Waterhouse Ln, Chester, CT 06412

      Last Sold Summary

      • 25% Above List Price
      • $187/SF
      • 69 Days On Market
      • Last Sold Price $710,000
      • Mar 28, 2024

      Last Listing Agent Craig Milton RE/MAX

  • 32 Gilbert Hill Rd, Chester, CT 06412

    $952,397

    Sold Jul 10, 2025

    32 Gilbert Hill Rd, Chester, CT 06412

    • 3 Beds
    • 3 Baths
    • 3,788 Sq Ft
    • Built 1986

    Last Sold Summary

    • 17% Below List Price
    • $251/SF
    • 70 Days On Market

    Current Estimated Value $995,922

    Last Listing Agent Steve Q Exclusive Properties

    32 Gilbert Hill Rd, Chester, CT 06412
    • 19 Hickory Hill Dr, Chester, CT 06412

      Est $767,051

      Not Listed For Sale

      19 Hickory Hill Dr, Chester, CT 06412

      • 3 Beds
      • 3 Baths
      • 2,646 Sq Ft
      • Built 1984
      19 Hickory Hill Dr, Chester, CT 06412

      Last Sold Summary

      • 14% Above List Price
      • $255/SF
      • 5 Days On Market
      • Last Sold Price $675,000
      • Oct 30, 2023

      Last Listing Agent Mark Capsalors Select Realty Associates, LLC

  • 31 Parkers Point Rd, Chester, CT 06412

    $3,100,000

    Sold Jun 10, 2025

    31 Parkers Point Rd, Chester, CT 06412

    • 3 Beds
    • 3.5 Baths
    • 4,727 Sq Ft
    • Built 2010

    Last Sold Summary

    • 11% Below List Price
    • $656/SF
    • 27 Days On Market

    Current Estimated Value $3,154,501

    Last Listing Agent Colette Harron William Pitt Sotheby's Int'l

    31 Parkers Point Rd, Chester, CT 06412
    • 2 Sypher Rd, Chester, CT 06412

      Est $519,512

      Not Listed For Sale

      2 Sypher Rd, Chester, CT 06412

      • 4 Beds
      • 2.5 Baths
      • 2,278 Sq Ft
      • Built 1970
      2 Sypher Rd, Chester, CT 06412

      Last Sold Summary

      • 15% Above List Price
      • $198/SF
      • 66 Days On Market
      • Last Sold Price $450,000
      • Jan 24, 2025

      Last Listing Agent Stacey Wyeth William Pitt

  • 9 Hickory Hill Dr, Chester, CT 06412

    $750,000

    Sold Feb 20, 2026

    9 Hickory Hill Dr, Chester, CT 06412

    • 3 Beds
    • 2.5 Baths
    • 2,888 Sq Ft
    • Built 1985

    Last Sold Summary

    • 6% Below List Price
    • $260/SF
    • 101 Days On Market

    Current Estimated Value $758,040

    Last Listing Agent Kathy Schellens William Pitt Sotheby's Int'l

    9 Hickory Hill Dr, Chester, CT 06412
    • 42 Railroad Ave, Chester, CT 06412

      Est $505,268

      Not Listed For Sale

      42 Railroad Ave, Chester, CT 06412

      • 4 Beds
      • 2 Baths
      • 2,092 Sq Ft
      • Built 1954
      42 Railroad Ave, Chester, CT 06412

      Last Sold Summary

      • 10% Above List Price
      • $220/SF
      • 117 Days On Market
      • Last Sold Price $460,000
      • Sep 26, 2024

      Last Listing Agent George Sznaj DB Associates of CT, LLC

  • 131 Middlesex Ave, Chester, CT 06412

    $530,000

    Sold Feb 26, 2026

    131 Middlesex Ave, Chester, CT 06412

    • 3 Beds
    • 2.5 Baths
    • 1,664 Sq Ft
    • Built 1930

    Last Sold Summary

    • 18% Below List Price
    • $319/SF
    • 158 Days On Market

    Current Estimated Value $539,849

    Last Listing Agent Claudia O'Connell William Raveis Real Estate

    131 Middlesex Ave, Chester, CT 06412
    • 16 Middlesex Ave, Chester, CT 06412

      Est $496,355

      Not Listed For Sale

      16 Middlesex Ave, Chester, CT 06412

      • 3 Beds
      • 2 Baths
      • 1,963 Sq Ft
      • Built 1945
      16 Middlesex Ave, Chester, CT 06412

      Last Sold Summary

      • 3% Above List Price
      • $245/SF
      • 59 Days On Market
      • Last Sold Price $480,000
      • May 03, 2024

      Last Listing Agent Chloe White KW Legacy Partners

  • 79 Cedar Lake Rd, Chester, CT 06412

    $875,000

    Sold Jul 25, 2025

    79 Cedar Lake Rd, Chester, CT 06412

    • 4 Beds
    • 3 Baths
    • 3,206 Sq Ft
    • Built 2004

    Last Sold Summary

    • 8% Below List Price
    • $273/SF
    • 83 Days On Market

    Current Estimated Value $891,806

    Last Listing Agent Bill Heenan William Raveis Real Estate

    79 Cedar Lake Rd, Chester, CT 06412
    • 8 Hickory Hill Dr, Chester, CT 06412

      Est $584,201

      Not Listed For Sale

      8 Hickory Hill Dr, Chester, CT 06412

      • 3 Beds
      • 2 Baths
      • 1,740 Sq Ft
      • Built 1984
      8 Hickory Hill Dr, Chester, CT 06412

      Last Sold Summary

      • 8% Above List Price
      • $310/SF
      • 1 Day On Market
      • Last Sold Price $540,000
      • Jul 12, 2023

      Last Listing Agent Laurie Mazzeo William Pitt

  • 21 E Liberty St, Chester, CT 06412

    $252,500

    Sold Nov 17, 2025

    21 E Liberty St, Chester, CT 06412

    • 2 Beds
    • 1 Bath
    • 1,012 Sq Ft
    • Built 1954

    Last Sold Summary

    • 28% Below List Price
    • $250/SF
    • 26 Days On Market

    Current Estimated Value $290,882

    Last Listing Agent Rachel Welch William Raveis Real Estate

    21 E Liberty St, Chester, CT 06412
    • 67 W Main St, Chester, CT 06412

      Est $657,453

      Not Listed For Sale

      67 W Main St, Chester, CT 06412

      • 3 Beds
      • 1.5 Baths
      • 1,916 Sq Ft
      • Built 1917
      67 W Main St, Chester, CT 06412

      Last Sold Summary

      • 3% Above List Price
      • $333/SF
      • 8 Days On Market
      • Last Sold Price $637,500
      • Jan 31, 2025

      Last Listing Agent Kyle Hinding Coldwell Banker Realty

  • 95 Cedar Swamp Rd, Chester, CT 06412

    $1,017,000

    Sold Oct 20, 2025

    95 Cedar Swamp Rd, Chester, CT 06412

    • 4 Beds
    • 3.5 Baths
    • 4,341 Sq Ft
    • Built 1999

    Last Sold Summary

    • $234/SF
    • 53 Days On Market

    Current Estimated Value $1,063,368

    Last Listing Agent Rachel Welch William Raveis Real Estate

    95 Cedar Swamp Rd, Chester, CT 06412
    • 17 Kings Hwy, Chester, CT 06412

      Est $784,080

      Not Listed For Sale

      17 Kings Hwy, Chester, CT 06412

      • 4 Beds
      • 2.5 Baths
      • 2,428 Sq Ft
      • Built 1988
      17 Kings Hwy, Chester, CT 06412

      Last Sold Summary

      • 17% Above List Price
      • $276/SF
      • 36 Days On Market
      • Last Sold Price $670,000
      • Jan 24, 2024

      Last Listing Agent Tracee Adams William Raveis Real Estate

  • 1 Ferry Rd, Chester, CT 06412

    $635,000

    Sold Apr 30, 2026

    1 Ferry Rd, Chester, CT 06412

    • 3 Beds
    • 3 Baths
    • 2,752 Sq Ft
    • Built 1790

    Last Sold Summary

    • 7% Below List Price
    • $231/SF
    • 86 Days On Market

    Current Estimated Value $649,808

    Last Listing Agent Jennifer D'Amato Real Broker CT, LLC

    1 Ferry Rd, Chester, CT 06412
    • 45 Winthrop Rd, Chester, CT 06412

      Est $553,144

      Not Listed For Sale

      45 Winthrop Rd, Chester, CT 06412

      • 4 Beds
      • 3 Baths
      • 1,972 Sq Ft
      • Built 1985
      45 Winthrop Rd, Chester, CT 06412

      Last Sold Summary

      • 32% Above List Price
      • $212/SF
      • 60 Days On Market
      • Last Sold Price $419,000
      • Jul 30, 2024

      Last Listing Agent Kira Coon William Raveis Real Estate

  • 67 Maple St, Chester, CT 06412

    $575,000

    Sold May 29, 2025

    67 Maple St, Chester, CT 06412

    • 3 Beds
    • 2.5 Baths
    • 1,803 Sq Ft
    • Built 2005

    Last Sold Summary

    • 10% Above List Price
    • $319/SF
    • 44 Days On Market

    Current Estimated Value $619,625

    Last Listing Agent Laura Cariati William Raveis Real Estate

    67 Maple St, Chester, CT 06412
    • 24 Deep Hollow Rd, Chester, CT 06412

      Est $530,683

      Not Listed For Sale

      24 Deep Hollow Rd, Chester, CT 06412

      • 4 Beds
      • 2 Baths
      • 1,927 Sq Ft
      • Built 1929
      24 Deep Hollow Rd, Chester, CT 06412

      Last Sold Summary

      • 9% Above List Price
      • $252/SF
      • 1 Day On Market
      • Last Sold Price $485,000
      • Jun 30, 2023

      Last Listing Agent Lisa Golebiewski Coldwell Banker Realty

  • 7 Old Depot Rd, Chester, CT 06412

    $975,000

    Sold Nov 17, 2025

    7 Old Depot Rd, Chester, CT 06412

    • 4 Beds
    • 2.5 Baths
    • 3,149 Sq Ft
    • Built 1908

    Last Sold Summary

    • 25% Below List Price
    • $310/SF
    • 236 Days On Market

    Current Estimated Value $982,840

    Last Listing Agent Colette Harron William Pitt Sotheby's Int'l

    7 Old Depot Rd, Chester, CT 06412
    • 53 Main St, Deep River, CT 06417

      Est $408,061

      Not Listed For Sale

      53 Main St, Deep River, CT 06417

      • 6 Beds
      • 2 Baths
      • 2,638 Sq Ft
      • Built 1750
      53 Main St, Deep River, CT 06417

      Last Sold Summary

      • 7% Above List Price
      • $144/SF
      • 12 Days On Market
      • Last Sold Price $380,000
      • May 30, 2023

      Last Listing Agent Craig Milton RE/MAX

  • 47 Ferry Rd, Chester, CT 06412

    $1,275,000

    Sold Dec 12, 2025

    47 Ferry Rd, Chester, CT 06412

    • 3 Beds
    • 3 Baths
    • 2,664 Sq Ft
    • Built 1939

    Last Sold Summary

    • 16% Above List Price
    • $479/SF
    • 9 Days On Market

    Current Estimated Value $1,211,814

    Last Listing Agent Mary Poola William Raveis Real Estate

    47 Ferry Rd, Chester, CT 06412
    • 187 Middlesex Ave, Chester, CT 06412

      Est $296,685

      Not Listed For Sale

      187 Middlesex Ave, Chester, CT 06412

      • 3 Beds
      • 1 Bath
      • 1,194 Sq Ft
      • Built 1965
      187 Middlesex Ave, Chester, CT 06412

      Last Sold Summary

      • 32% Above List Price
      • $188/SF
      • 58 Days On Market
      • Last Sold Price $225,000
      • Oct 25, 2024

      Last Listing Agent Team DAnna Statewide Premier Prop. LLC

  • 35 Maple St, Chester, CT 06412

    $780,000

    Sold Jan 15, 2026

    35 Maple St, Chester, CT 06412

    • 3 Beds
    • 2 Baths
    • 1,772 Sq Ft
    • Built 1765

    Last Sold Summary

    • 2% Below List Price
    • $440/SF
    • 52 Days On Market

    Current Estimated Value $781,372

    Last Listing Agent Deborah Rowe William Raveis Real Estate

    35 Maple St, Chester, CT 06412
    • 6 Hickory Hill Dr, Chester, CT 06412

      Est $508,416

      Not Listed For Sale

      6 Hickory Hill Dr, Chester, CT 06412

      • 3 Beds
      • 2 Baths
      • 1,821 Sq Ft
      • Built 1964
      6 Hickory Hill Dr, Chester, CT 06412

      Last Sold Summary

      • 36% Above List Price
      • $206/SF
      • 1 Day On Market
      • Last Sold Price $375,000
      • Dec 21, 2023

      Last Listing Agent Robert Clermont Clermont Real Estate

  • 226 Middlesex Ave, Chester, CT 06412

    $695,000

    Sold May 15, 2026

    226 Middlesex Ave, Chester, CT 06412

    • 4 Beds
    • 2.5 Baths
    • 2,029 Sq Ft
    • Built 1976

    Last Sold Summary

    • $343/SF
    • 30 Days On Market

    Current Estimated Value $590,969

    Last Listing Agent Peg Mitchel Coldwell Banker Realty

    226 Middlesex Ave, Chester, CT 06412
    • 3 Cross Rd, Chester, CT 06412

      Est $446,185

      Not Listed For Sale

      3 Cross Rd, Chester, CT 06412

      • 3 Beds
      • 2 Baths
      • 1,440 Sq Ft
      • Built 1966
      3 Cross Rd, Chester, CT 06412

      Last Sold Summary

      • 27% Above List Price
      • $243/SF
      • 48 Days On Market
      • Last Sold Price $350,000
      • Apr 23, 2024

      Last Listing Agent Courtney Ciscato RE/MAX

  • 6 Pelton Hill Rd, Chester, CT 06412

    $813,500

    Sold Apr 30, 2026

    6 Pelton Hill Rd, Chester, CT 06412

    • 3 Beds
    • 1.5 Baths
    • 1,982 Sq Ft
    • Built 1865

    Last Sold Summary

    • 10% Above List Price
    • $410/SF
    • 23 Days On Market

    Current Estimated Value $721,338

    Last Listing Agent John Zubretsky Century 21 AllPoints Realty

    6 Pelton Hill Rd, Chester, CT 06412
    • 49 Parkers Point Rd, Chester, CT 06412

      Est $2,211,643

      Not Listed For Sale

      49 Parkers Point Rd, Chester, CT 06412

      • 6 Beds
      • 4.5 Baths
      • 3,968 Sq Ft
      • Built 1987
      49 Parkers Point Rd, Chester, CT 06412

      Last Sold Summary

      • 4% Below List Price
      • $580/SF
      • 29 Days On Market
      • Last Sold Price $2,300,000
      • Nov 20, 2023

      Last Listing Agent Tammy Tinnerello William Pitt

  • 13 Cross Rd, Chester, CT 06412

    $610,000

    Sold Dec 01, 2025

    13 Cross Rd, Chester, CT 06412

    • 3 Beds
    • 2.5 Baths
    • 2,324 Sq Ft
    • Built 2005

    Last Sold Summary

    • 6% Below List Price
    • $262/SF
    • 90 Days On Market

    Current Estimated Value $640,677

    Last Listing Agent Curt Clemens Jr. Century 21 Clemens Group

    13 Cross Rd, Chester, CT 06412
    • 19 W Main St, Chester, CT 06412

      Not Listed For Sale

      19 W Main St, Chester, CT 06412

      • 4 Beds
      • 3.5 Baths
      • 4,205 Sq Ft
      • Built 1999
      19 W Main St, Chester, CT 06412

      Last Sold Summary

      • $324/SF
      • 136 Days On Market
      • Last Sold Price $1,363,500
      • Apr 15, 2025

      Last Listing Agent Michael Marsden Compass Connecticut, LLC

  • 36 Kings Hwy, Chester, CT 06412

    $469,900

    Sold Dec 18, 2025

    36 Kings Hwy, Chester, CT 06412

    • 4 Beds
    • 2 Baths
    • 1,516 Sq Ft
    • Built 1930

    Last Sold Summary

    • $310/SF
    • 37 Days On Market

    Current Estimated Value $475,806

    Last Listing Agent Craig Milton Re/Max Valley Shore

    36 Kings Hwy, Chester, CT 06412
    • 56 Castle View Dr, Chester, CT 06412

      Est $478,418

      Not Listed For Sale

      56 Castle View Dr, Chester, CT 06412

      • 3 Beds
      • 3 Baths
      • 2,268 Sq Ft
      • Built 1963
      56 Castle View Dr, Chester, CT 06412

      Last Sold Summary

      • 11% Above List Price
      • $190/SF
      • 40 Days On Market
      • Last Sold Price $430,000
      • Nov 27, 2024

      Last Listing Agent Sharon Linder Berkshire Hathaway Home Services

  • 8 Butter Jones Rd, Chester, CT 06412

    $715,000

    Sold Mar 06, 2026

    8 Butter Jones Rd, Chester, CT 06412

    • 3 Beds
    • 2.5 Baths
    • 2,139 Sq Ft
    • Built 1984

    Last Sold Summary

    • 10% Below List Price
    • $334/SF
    • 175 Days On Market

    Current Estimated Value $696,300

    Last Listing Agent Amy Graham William Pitt Sotheby's Int'l

    8 Butter Jones Rd, Chester, CT 06412
    • 21 Baker Rd, Chester, CT 06412

      Est $701,501

      Not Listed For Sale

      21 Baker Rd, Chester, CT 06412

      • 3 Beds
      • 3.5 Baths
      • 3,178 Sq Ft
      • Built 1991
      21 Baker Rd, Chester, CT 06412

      Last Sold Summary

      • 38% Above List Price
      • $160/SF
      • 8 Days On Market
      • Last Sold Price $510,000
      • Jun 06, 2023

      Last Listing Agent Michael Marsden Compass Connecticut, LLC

Showing Results 41 - 80, Page 2 of 18

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