1,669

Chester, CT Homes

Section Image
    • 22 Waterhouse Ln, Chester, CT 06412

      Est $942,426

      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

      • 69 Days On Market

      Last Listing Agent Craig Milton Re/Max Valley Shore

  • 25 Goose Hill Rd, Chester, CT 06412
    25 Goose Hill Rd, Chester, CT 06412
    25 Goose Hill Rd, Chester, CT 06412
    /24

    $385,000

    Pending
    • 2 Beds
    • 1.5 Baths
    • 1,454 Sq Ft

    25 Goose Hill Rd, Chester, CT 06412

    Multiple offers - Seller requests highest and best, Monday, 7/27 by 5PM. No escalation clauses. Fantastic Opportunity in the Heart of Chester! Discover the potential of this charming 2 Bedroom, 1.5 bath ranch, perfectly situated within walking distance to downtown Chester. The highlight of this home is a newer, heated sunroom boasting wood floors, cathedral ceilings and an abundance of natural

    Janet Mashia William Pitt Sotheby's Int'l

    25 Goose Hill Rd, Chester, CT 06412
  • 28 S Wig Hill Rd, Chester, CT 06412

    $580,000

    Sold Dec 10, 2025

    28 S Wig Hill Rd, Chester, CT 06412

    • 2 Beds
    • 3 Baths
    • 3,091 Sq Ft
    • Built 1770

    Last Sold Summary

    • 10% Below List Price
    • $188/SF
    • 138 Days On Market

    Last Listing Agent Andrew O'Reilly Seaport Real Estate Services

    28 S Wig Hill Rd, Chester, CT 06412
    • 19 Hickory Hill Dr, Chester, CT 06412

      Est $781,815

      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

      • 5 Days On Market

      Last Listing Agent Mark Capsalors Select Realty Associates, LLC

  • 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 $565,224

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

    23 Spring St, Chester, CT 06412
    • 2 Sypher Rd, Chester, CT 06412

      Est $536,252

      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

      • 66 Days On Market

      Last Listing Agent Stacey Wyeth William Pitt Sotheby's Int'l

  • 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 $383,293

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

    50 Bokum Rd, Chester, CT 06412
    • 42 Railroad Ave, Chester, CT 06412

      Est $443,781

      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

      • 117 Days On Market

      Last Listing Agent George Sznaj DB Associates of CT, LLC

  • 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 $765,903

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

    9 Hickory Hill Dr, Chester, CT 06412
    • 16 Middlesex Ave, Chester, CT 06412

      Est $516,810

      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

      • 59 Days On Market

      Last Listing Agent Chloe White KW Legacy Partners

  • 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 $537,227

    Last Listing Agent Claudia O'Connell William Raveis Real Estate

    131 Middlesex Ave, Chester, CT 06412
    • 15 Gilbert Hill Rd, Chester, CT 06412

      Est $1,011,816

      Not Listed For Sale

      15 Gilbert Hill Rd, Chester, CT 06412

      • 4 Beds
      • 3 Baths
      • 3,054 Sq Ft
      • Built 1950
      15 Gilbert Hill Rd, Chester, CT 06412

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Angela Ruel Berkshire Hathaway NE Prop.

  • 81 Main St, Chester, CT 06412

    $618,000

    Sold Jun 11, 2026

    81 Main St, Chester, CT 06412

    • 2 Beds
    • 2 Baths
    • 1,128 Sq Ft
    • Built 1950

    Last Sold Summary

    • 12% Above List Price
    • $548/SF
    • 4 Days On Market

    Current Estimated Value $602,292

    Last Listing Agent Sue Woods William Pitt Sotheby's Int'l

    81 Main St, Chester, CT 06412
    • 67 W Main St, Chester, CT 06412

      Est $688,047

      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

      • 8 Days On Market

      Last Listing Agent Kyle Hinding Coldwell Banker Realty

  • 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 $284,566

    Last Listing Agent Rachel Welch William Raveis Real Estate

    21 E Liberty St, Chester, CT 06412
    • 17 Kings Hwy, Chester, CT 06412

      Est $782,789

      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

      • 36 Days On Market

      Last Listing Agent Tracee Adams William Raveis Real Estate

  • 19 Castle View Dr, Chester, CT 06412

    $470,000

    Sold Jun 12, 2026

    19 Castle View Dr, Chester, CT 06412

    • 3 Beds
    • 1.5 Baths
    • 1,092 Sq Ft
    • Built 1960

    Last Sold Summary

    • 2% Above List Price
    • $430/SF
    • 13 Days On Market

    Current Estimated Value $433,416

    Last Listing Agent Donna Genovese Great Estates, CT

    19 Castle View Dr, Chester, CT 06412
    • 45 Winthrop Rd, Chester, CT 06412

      Est $546,432

      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

      • 60 Days On Market

      Last Listing Agent Kira Coon William Raveis Real Estate

  • 11 Kings Hwy, Chester, CT 06412

    $225,000

    Sold Jun 10, 2026

    11 Kings Hwy, Chester, CT 06412

    • Land
    • 1.5 Acres
    • $150,000 per Acre

    Last Sold Summary

    • 13% Above List Price
    • 1,286 Days On Market

    Last Listing Agent Rachel Welch William Raveis Real Estate

    11 Kings Hwy, Chester, CT 06412
    • 24 E Liberty St, Chester, CT 06412

      Est $539,335

      Not Listed For Sale

      24 E Liberty St, Chester, CT 06412

      • 4 Beds
      • 2 Baths
      • 1,926 Sq Ft
      • Built 1790
      24 E Liberty St, Chester, CT 06412

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Bonnie Fillion Berkshire Hathaway NE Prop.

  • 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 $1,058,607

    Last Listing Agent Rachel Welch William Raveis Real Estate

    95 Cedar Swamp Rd, Chester, CT 06412
    • 187 Middlesex Ave, Chester, CT 06412

      Est $309,174

      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

      • 58 Days On Market

      Last Listing Agent Team DAnna Statewide Premier Prop. LLC

  • 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 $639,728

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

    1 Ferry Rd, Chester, CT 06412
    • 6 Hickory Hill Dr, Chester, CT 06412

      Est $528,873

      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

      • 1 Day On Market

      Last Listing Agent Robert Clermont Clermont Real Estate

  • 59 Wig Hill Rd, Chester, CT 06412

    $695,000

    Sold Jul 02, 2026

    59 Wig Hill Rd, Chester, CT 06412

    • 5 Beds
    • 2.5 Baths
    • 3,862 Sq Ft
    • Built 1977

    Last Sold Summary

    • 4% Below List Price
    • $180/SF
    • 43 Days On Market

    Current Estimated Value $759,746

    Last Listing Agent Joseph Kelly William Pitt Sotheby's Int'l

    59 Wig Hill Rd, Chester, CT 06412
    • 3 Cross Rd, Chester, CT 06412

      Est $461,786

      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

      • 48 Days On Market

      Last Listing Agent Courtney Ciscato RE/MAX One

  • 1 Kirtland Ave, Chester, CT 06412

    $452,000

    Sold Aug 25, 2026

    1 Kirtland Ave, Chester, CT 06412

    • 3 Beds
    • 1.5 Baths
    • 1,198 Sq Ft
    • Built 1968

    Last Sold Summary

    • 3% Above List Price
    • $377/SF
    • 44 Days On Market

    Current Estimated Value $433,443

    Last Listing Agent Craig Milton Re/Max Valley Shore

    1 Kirtland Ave, Chester, CT 06412
    • 49 Parkers Point Rd, Chester, CT 06412

      Est $2,311,038

      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

      • 29 Days On Market

      Last Listing Agent Tammy Tinnerello William Pitt Sotheby's Int'l

  • 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 $993,177

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

    7 Old Depot 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

      • 136 Days On Market

      Last Listing Agent Michael Marsden Compass Connecticut, LLC

  • 12 Meadow Ln, Chester, CT 06412

    $515,000

    Sold Jul 27, 2026

    12 Meadow Ln, Chester, CT 06412

    • 3 Beds
    • 3 Baths
    • 2,971 Sq Ft
    • Built 1984

    Last Sold Summary

    • 2% Below List Price
    • $173/SF
    • 31 Days On Market

    Current Estimated Value $539,857

    Last Listing Agent Kelly Puorro Puorro Realty Group

    12 Meadow Ln, Chester, CT 06412
    • 56 Castle View Dr, Chester, CT 06412

      Est $510,837

      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

      • 40 Days On Market

      Last Listing Agent Sharon Linder Berkshire Hathaway NE Prop.

  • 275 W Main St, Chester, CT 06412

    $495,000

    Sold Jun 05, 2026

    275 W Main St, Chester, CT 06412

    • 4 Beds
    • 2 Baths
    • 1,906 Sq Ft
    • Built 1971

    Last Sold Summary

    • 2% Above List Price
    • $260/SF
    • 6 Days On Market

    Current Estimated Value $500,163

    Last Listing Agent Kelly Puorro Puorro Realty Group

    275 W Main St, Chester, CT 06412
    • 25 Gilbert Hill Rd, Chester, CT 06412

      Est $1,154,763

      Not Listed For Sale

      25 Gilbert Hill Rd, Chester, CT 06412

      • 4 Beds
      • 4.5 Baths
      • 3,351 Sq Ft
      • Built 1987
      25 Gilbert Hill Rd, Chester, CT 06412

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Robin Linares William Pitt Sotheby's Int'l

  • 22 Goose Hill Rd, Chester, CT 06412

    $500,000

    Sold Sep 02, 2026

    22 Goose Hill Rd, Chester, CT 06412

    • 3 Beds
    • 3 Baths
    • 1,714 Sq Ft
    • Built 1970

    Last Sold Summary

    • 11% Above List Price
    • $292/SF
    • 47 Days On Market

    Current Estimated Value $455,340

    Last Listing Agent Kelly Puorro Puorro Realty Group

    22 Goose Hill Rd, Chester, CT 06412
    • 30 Middlesex Ave, Chester, CT 06412

      Est $420,452

      Not Listed For Sale

      30 Middlesex Ave, Chester, CT 06412

      • 2 Beds
      • 1.5 Baths
      • 1,362 Sq Ft
      • Built 1922
      30 Middlesex Ave, Chester, CT 06412

      Last Sold Summary

      • 73 Days On Market

      Last Listing Agent Agota Perry-Hill William Raveis Real Estate

  • 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 $1,256,709

    Last Listing Agent Mary Poola William Raveis Real Estate

    47 Ferry Rd, Chester, CT 06412
    • 28 Goose Hill Rd, Chester, CT 06412

      Est $667,017

      Not Listed For Sale

      28 Goose Hill Rd, Chester, CT 06412

      • 3 Beds
      • 3 Baths
      • 2,398 Sq Ft
      • Built 1870
      28 Goose Hill Rd, Chester, CT 06412

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Cheryl Bergeron-Lucca LPT Realty - IConn Team

  • 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 $780,696

    Last Listing Agent Deborah Rowe William Raveis Real Estate

    35 Maple St, Chester, CT 06412
    • 39 Castle View Dr, Chester, CT 06412

      Est $517,737

      Not Listed For Sale

      39 Castle View Dr, Chester, CT 06412

      • 3 Beds
      • 3.5 Baths
      • 2,208 Sq Ft
      • Built 2013
      39 Castle View Dr, Chester, CT 06412

      Last Sold Summary

      • 95 Days On Market

      Last Listing Agent Gene Pica RE/MAX Alliance

Showing Results 41 - 80, Page 2 of 18

Connecticut Middlesex County

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