5,004

Winchester, CT Homes

Section Image
  • 162 Spencer Hill Rd, Winsted, CT 06098

    $650,000

    Sold Jun 12, 2026

    162 Spencer Hill Rd, Winsted, CT 06098

    • 3 Beds
    • 2.5 Baths
    • 2,144 Sq Ft
    • Built 2000

    Last Sold Summary

    • 4% Above List Price
    • $303/SF
    • 9 Days On Market

    Current Estimated Value $631,137

    Last Listing Agent Kelly Sullivan Sullivan Real Estate Inc

    162 Spencer Hill Rd, Winsted, CT 06098
    • 80 John St, Winsted, CT 06098

      Est $358,183

      Not Listed For Sale

      80 John St, Winsted, CT 06098

      • 2 Beds
      • 2 Baths
      • 1,514 Sq Ft
      • Built 1875
      80 John St, Winsted, CT 06098

      Last Sold Summary

      • 81 Days On Market

      Last Listing Agent Katie Breitkreutz Dave Jones Realty, LLC

  • 106A Pinney St, Colebrook, CT 06021

    $550,000

    Sold Apr 02, 2026

    106A Pinney St, Colebrook, CT 06021

    • 3 Beds
    • 2 Baths
    • 1,745 Sq Ft
    • Built 1997

    Last Sold Summary

    • 2% Below List Price
    • $315/SF
    • 158 Days On Market

    Current Estimated Value $563,910

    Last Listing Agent Kelly Sullivan Sullivan Real Estate Inc

    106A Pinney St, Colebrook, CT 06021
    • 224 Smith Hill Rd, Winsted, CT 06098

      Est $333,470

      Not Listed For Sale

      224 Smith Hill Rd, Winsted, CT 06098

      • 3 Beds
      • 1.5 Baths
      • 1,178 Sq Ft
      • Built 1971
      224 Smith Hill Rd, Winsted, CT 06098

      Last Sold Summary

      • 49 Days On Market

      Last Listing Agent Fern Nadolny Farmingbury Real Estate Inc

  • 174 Wallens St Unit B6, Winsted, CT 06098

    $250,000

    Sold Jan 23, 2026

    174 Wallens St Unit B6, Winsted, CT 06098

    • 2 Beds
    • 2 Baths
    • 1,352 Sq Ft
    • Built 2008

    Last Sold Summary

    • 2% Above List Price
    • $185/SF
    • 4 Days On Market

    Last Listing Agent David Sartirana Northwest CT Realty

    174 Wallens St Unit B6, Winsted, CT 06098
    • 180 Shore Dr, Winsted, CT 06098

      Est $710,778

      Not Listed For Sale

      180 Shore Dr, Winsted, CT 06098

      • 3 Beds
      • 2 Baths
      • 1,131 Sq Ft
      • Built 1978
      180 Shore Dr, Winsted, CT 06098

      Last Sold Summary

      • 74 Days On Market

      Last Listing Agent David Sartirana Northwest CT Realty

  • 43 Wallens St, Winsted, CT 06098

    $250,000

    Sold Mar 01, 2026

    43 Wallens St, Winsted, CT 06098

    • 4 Beds
    • 2 Baths
    • 1,971 Sq Ft
    • Built 1900

    Last Sold Summary

    • 9% Below List Price
    • $127/SF
    • 5 Days On Market

    Current Estimated Value $265,798

    Last Listing Agent Kristen Duchene Litchfield County Real Estate

    43 Wallens St, Winsted, CT 06098
    • 71 Ridge St, Winsted, CT 06098

      Est $279,144

      Not Listed For Sale

      71 Ridge St, Winsted, CT 06098

      • 3 Beds
      • 1 Bath
      • 1,044 Sq Ft
      • Built 1958
      71 Ridge St, Winsted, CT 06098

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent David Sartirana Northwest CT Realty

  • 548 E Wakefield Blvd, Winsted, CT 06098

    $425,000

    Sold Oct 28, 2025

    548 E Wakefield Blvd, Winsted, CT 06098

    • 2 Beds
    • 1 Bath
    • 512 Sq Ft
    • Built 1936

    Last Sold Summary

    • 8% Above List Price
    • $830/SF
    • 60 Days On Market

    Current Estimated Value $470,407

    Last Listing Agent Amy Rio Better Homes and Gardens Real Estate Executive Real Estate

    548 E Wakefield Blvd, Winsted, CT 06098
    • 88 Munro Place, Winsted, CT 06098

      Est $373,890

      Not Listed For Sale

      88 Munro Place, Winsted, CT 06098

      • 4 Beds
      • 2 Baths
      • 2,800 Sq Ft
      • Built 1898
      88 Munro Place, Winsted, CT 06098

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Melanie LeRoy William Raveis Real Estate

  • 435 W Wakefield Blvd, Winsted, CT 06098

    $1,215,000

    Sold Sep 10, 2025

    435 W Wakefield Blvd, Winsted, CT 06098

    • 8 Beds
    • 4.5 Baths
    • 5,231 Sq Ft
    • Built 1930

    Last Sold Summary

    • 29% Below List Price
    • $232/SF
    • 347 Days On Market

    Current Estimated Value $1,317,297

    Last Listing Agent Heidi Picard-Ramsay Berkshire Hathaway NE Prop.

    435 W Wakefield Blvd, Winsted, CT 06098
    • 157 Newfield Rd, Winsted, CT 06098

      Est $324,577

      Not Listed For Sale

      157 Newfield Rd, Winsted, CT 06098

      • 1 Bed
      • 1 Bath
      • 1,345 Sq Ft
      • Built 1785
      157 Newfield Rd, Winsted, CT 06098

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Michelina Marchlinski The Washington Agency

  • 258 Perch Rock Trail, Winsted, CT 06098

    $925,000

    Sold Jun 04, 2026

    258 Perch Rock Trail, Winsted, CT 06098

    • 4 Beds
    • 2 Baths
    • 1,373 Sq Ft
    • Built 1922

    Last Sold Summary

    • 16% Above List Price
    • $674/SF
    • 6 Days On Market

    Current Estimated Value $903,142

    Last Listing Agent Nancy Reardon Berkshire Hathaway NE Prop.

    258 Perch Rock Trail, Winsted, CT 06098
    • 8 Colony Dr, Winsted, CT 06098

      Est $315,567

      Not Listed For Sale

      8 Colony Dr, Winsted, CT 06098

      • 2 Beds
      • 3 Baths
      • 1,408 Sq Ft
      • Built 1965
      8 Colony Dr, Winsted, CT 06098

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent David Taylor Elyse Harney Real Estate

  • 42 Maloney Ct, Winsted, CT 06098

    $240,000

    Sold Sep 09, 2025

    42 Maloney Ct, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft
    • Built 1956

    Last Sold Summary

    • 4% Below List Price
    • $238/SF
    • 6 Days On Market

    Current Estimated Value $245,912

    Last Listing Agent James Walsh James Walsh

    42 Maloney Ct, Winsted, CT 06098
    • 18 Upland Rd, Winsted, CT 06098

      Est $292,155

      Not Listed For Sale

      18 Upland Rd, Winsted, CT 06098

      • 5 Beds
      • 2 Baths
      • 2,338 Sq Ft
      • Built 1886
      18 Upland Rd, Winsted, CT 06098

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Linda Ganem Borla & Associates Real Estate

  • 157 Elm St, Winsted, CT 06098

    $330,000

    Sold Mar 10, 2026

    157 Elm St, Winsted, CT 06098

    • 6 Beds
    • 2.5 Baths
    • 2,376 Sq Ft
    • Built 1900

    Last Sold Summary

    • 3% Below List Price
    • $139/SF
    • 65 Days On Market

    Current Estimated Value $332,526

    Last Listing Agent Doreen Gagnon Coldwell Banker Realty

    157 Elm St, Winsted, CT 06098
    • 103 Meadow St Unit 105, Winsted, CT 06098

      Not Listed For Sale

      103 Meadow St Unit 105, Winsted, CT 06098

      • 6 Beds
      • 3.5 Baths
      • 3,762 Sq Ft
      • Built 1886
      103 Meadow St Unit 105, Winsted, CT 06098

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Christine Hunter Hunter Real Estate, LLC

  • 111 Riverton Rd Unit 37, Winsted, CT 06098

    $198,000

    Sold Oct 28, 2025

    111 Riverton Rd Unit 37, Winsted, CT 06098

    • 2 Beds
    • 1.5 Baths
    • 1,204 Sq Ft
    • Built 1987

    Last Sold Summary

    • $164/SF
    • 48 Days On Market

    Current Estimated Value $212,676

    Last Listing Agent Sandra Marchetti The Washington Agency

    111 Riverton Rd Unit 37, Winsted, CT 06098
    • 38 S Main St, Winsted, CT 06098

      Est $240,749

      Not Listed For Sale

      38 S Main St, Winsted, CT 06098

      • 3 Beds
      • 2 Baths
      • 1,520 Sq Ft
      • Built 1900
      38 S Main St, Winsted, CT 06098

      Last Sold Summary

      • 104 Days On Market

      Last Listing Agent Stephen Simard Real Broker CT, LLC

  • 107 Peck Rd, Winsted, CT 06098

    $309,250

    Sold Feb 06, 2026

    107 Peck Rd, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1983

    Last Sold Summary

    • 9% Below List Price
    • $322/SF
    • 54 Days On Market

    Current Estimated Value $322,569

    Last Listing Agent Rebecca Doh W. Raveis Lifestyles Realty

    107 Peck Rd, Winsted, CT 06098
    • 206 Walnut St, Winsted, CT 06098

      Est $294,107

      Not Listed For Sale

      206 Walnut St, Winsted, CT 06098

      • 3 Beds
      • 1 Bath
      • 1,100 Sq Ft
      • Built 1990
      206 Walnut St, Winsted, CT 06098

      Last Sold Summary

      • 69 Days On Market

      Last Listing Agent Johanna Stanko Berkshire Hathaway NE Prop.

  • 159 Sandy Brook Rd, Colebrook, CT 06021

    $440,000

    Sold Oct 29, 2025

    159 Sandy Brook Rd, Colebrook, CT 06021

    • 4 Beds
    • 1.5 Baths
    • 1,940 Sq Ft
    • Built 1800

    Last Sold Summary

    • 11% Below List Price
    • $227/SF
    • 73 Days On Market

    Current Estimated Value $452,721

    Last Listing Agent Lenore Mallett William Pitt Sotheby's Int'l

    159 Sandy Brook Rd, Colebrook, CT 06021
    • 114 Oak St, Winsted, CT 06098

      Est $315,349

      Not Listed For Sale

      114 Oak St, Winsted, CT 06098

      • 3 Beds
      • 1.5 Baths
      • 2,192 Sq Ft
      • Built 1900
      114 Oak St, Winsted, CT 06098

      Last Sold Summary

      • 84 Days On Market

      Last Listing Agent David Sartirana Northwest CT Realty

  • 350 Walnut St, Winsted, CT 06098

    $285,000

    Sold Jun 22, 2026

    350 Walnut St, Winsted, CT 06098

    • 2 Beds
    • 1 Bath
    • 720 Sq Ft
    • Built 1950

    Last Sold Summary

    • 2% Above List Price
    • $396/SF
    • 16 Days On Market

    Current Estimated Value $277,501

    Last Listing Agent Vincent Miller Hudson Home Services LLC

    350 Walnut St, Winsted, CT 06098
    • 111 Riverton Rd Unit 9, Winsted, CT 06098

      Est $211,620

      Not Listed For Sale

      111 Riverton Rd Unit 9, Winsted, CT 06098

      • 2 Beds
      • 1.5 Baths
      • 1,204 Sq Ft
      • Built 1987
      111 Riverton Rd Unit 9, Winsted, CT 06098

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Kathleen Miller CT Home Pro, LLC

  • 351 Platt Hill Rd, Winsted, CT 06098

    $370,000

    Sold Apr 17, 2026

    351 Platt Hill Rd, Winsted, CT 06098

    • 3 Beds
    • 2 Baths
    • 1,715 Sq Ft
    • Built 1960

    Last Sold Summary

    • $216/SF
    • 33 Days On Market

    Current Estimated Value $374,382

    Last Listing Agent Valerie Nash KW Legacy Partners

    351 Platt Hill Rd, Winsted, CT 06098
    • 150 Meadow St, Winsted, CT 06098

      Est $283,399

      Not Listed For Sale

      150 Meadow St, Winsted, CT 06098

      • 4 Beds
      • 2 Baths
      • 2,094 Sq Ft
      • Built 1860
      150 Meadow St, Winsted, CT 06098

      Last Sold Summary

      • 80 Days On Market

      Last Listing Agent David Sartirana Northwest CT Realty

  • 179 Gilbert Ave, Winsted, CT 06098

    $275,000

    Sold Sep 13, 2025

    179 Gilbert Ave, Winsted, CT 06098

    • 3 Beds
    • 2 Baths
    • 1,744 Sq Ft
    • Built 1981

    Last Sold Summary

    • 6% Above List Price
    • $158/SF
    • 46 Days On Market

    Current Estimated Value $294,993

    Last Listing Agent David Sartirana Northwest CT Realty

    179 Gilbert Ave, Winsted, CT 06098
    • 121 Highview Dr, Winsted, CT 06098

      Est $358,501

      Not Listed For Sale

      121 Highview Dr, Winsted, CT 06098

      • 4 Beds
      • 3 Baths
      • 2,148 Sq Ft
      • Built 1974
      121 Highview Dr, Winsted, CT 06098

      Last Sold Summary

      • 73 Days On Market

      Last Listing Agent David Sartirana Northwest CT Realty

  • 149 E Mountain Ave, Winsted, CT 06098

    $290,000

    Sold Jun 30, 2026

    149 E Mountain Ave, Winsted, CT 06098

    • 2 Beds
    • 1 Bath
    • 993 Sq Ft
    • Built 1948

    Last Sold Summary

    • 5% Above List Price
    • $292/SF
    • 2 Days On Market

    Current Estimated Value $269,456

    Last Listing Agent John Lepore Berkshire Hathaway NE Prop.

    149 E Mountain Ave, Winsted, CT 06098
    • 208 Coe St, Winsted, CT 06098

      Not Listed For Sale

      208 Coe St, Winsted, CT 06098

      • 5 Beds
      • 5.5 Baths
      • 5,284 Sq Ft
      • Built 1942
      208 Coe St, Winsted, CT 06098

      Last Sold Summary

      • 85 Days On Market

      Last Listing Agent Sharon Chase Coldwell Banker Realty

  • 426 Platt Hill Rd, Winsted, CT 06098

    $660,000

    Sold Aug 14, 2026

    426 Platt Hill Rd, Winsted, CT 06098

    • 3 Beds
    • 2.5 Baths
    • 3,086 Sq Ft
    • Built 1976

    Last Sold Summary

    • 3% Below List Price
    • $214/SF
    • 53 Days On Market

    Current Estimated Value $631,300

    Last Listing Agent Mary Mary LeBlanc Realty

    426 Platt Hill Rd, Winsted, CT 06098
    • 22 Adams St, Winsted, CT 06098

      Est $257,543

      Not Listed For Sale

      22 Adams St, Winsted, CT 06098

      • 3 Beds
      • 1.5 Baths
      • 1,200 Sq Ft
      • Built 1956
      22 Adams St, Winsted, CT 06098

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Christine Hunter Hunter Real Estate, LLC

  • 117 Blue St, Winchester, CT 06790

    $68,000

    Sold May 15, 2026

    117 Blue St, Winchester, CT 06790

    • Land
    • 10,890 Sq Ft
    • $272,000 per Acre

    Last Sold Summary

    • 70% Above List Price
    • 3 Days On Market

    Last Listing Agent Annie Q Simard LPT Realty

    117 Blue St, Winchester, CT 06790
    • 184 Newfield Rd, Winsted, CT 06098

      Not Listed For Sale

      184 Newfield Rd, Winsted, CT 06098

      • 2 Beds
      • 1.5 Baths
      • 1,598 Sq Ft
      • Built 1995
      184 Newfield Rd, Winsted, CT 06098

      Last Sold Summary

      • 97 Days On Market

      Last Listing Agent Heidi Picard-Ramsay Berkshire Hathaway NE Prop.

  • 381 Smith Hill Rd, Colebrook, CT 06021

    $2,200,000

    Sold Oct 21, 2025

    381 Smith Hill Rd, Colebrook, CT 06021

    • 4 Beds
    • 3.5 Baths
    • 4,327 Sq Ft
    • Built 1795

    Last Sold Summary

    • $508/SF
    • 28 Days On Market

    Last Listing Agent Elvia Gignoux William Pitt Sotheby's Int'l

    381 Smith Hill Rd, Colebrook, CT 06021
    • 17 Chestnut St, Winsted, CT 06098

      Est $239,571

      Not Listed For Sale

      17 Chestnut St, Winsted, CT 06098

      • 5 Beds
      • 2 Baths
      • 1,932 Sq Ft
      • Built 1900
      17 Chestnut St, Winsted, CT 06098

      Last Sold Summary

      • 84 Days On Market

      Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

  • 99 Hubbard St, Winsted, CT 06098

    $40,000

    Sold Jul 22, 2026

    99 Hubbard St, Winsted, CT 06098

    • Land
    • 16,117 Sq Ft
    • $108,108 per Acre

    Last Sold Summary

    • 18% Below List Price
    • 471 Days On Market

    Last Listing Agent David Sartirana Northwest CT Realty

    99 Hubbard St, Winsted, CT 06098
    • 39 Baker St, Winsted, CT 06098

      Est $238,606

      Not Listed For Sale

      39 Baker St, Winsted, CT 06098

      • 5 Beds
      • 2 Baths
      • 1,612 Sq Ft
      • Built 1900
      39 Baker St, Winsted, CT 06098

      Last Sold Summary

      • 166 Days On Market

      Last Listing Agent Christine Hunter Hunter Real Estate, LLC

Showing Results 281 - 320, Page 8 of 18

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