5,132

Winchester, CT Homes

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  • /19

    $469,900

    • 3 Beds
    • 2 Baths
    • 1,768 Sq Ft

    9 Loomis St, Winsted, CT 06098

    Spacious 3 to 4 Bedroom Colonial Style Home on a 0.35 Acre Lot, plus located on a No Through Street. OPEN FLOOR PLAN. Beautifully Remodeled from "TOP TO BOTTOM" for Energy Efficient Living. Redesigned Country Style Kitchen offers Ample Cabinetry and includes New Oven/Range, Microwave, Refrigerator & Dishwasher.. 27' x 12' Living/Dining Combo with Bay/Bow Window that takes in Natural Light on

    Marshall Cohen Cohen Agency

    9 Loomis St, Winsted, CT 06098
  • 126 Williams Ave, Winsted, CT 06098

    $292,000

    Sold Jul 25, 2025

    126 Williams Ave, Winsted, CT 06098

    • 6 Beds
    • 2 Baths
    • 2,225 Sq Ft
    • Built 1890

    Last Sold Summary

    • 2% Above List Price
    • $131/SF
    • 42 Days On Market

    Current Estimated Value $284,692

    Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

    126 Williams Ave, Winsted, CT 06098
    • 19 Cottage St, Winsted, CT 06098

      Est $356,952

      Not Listed For Sale

      19 Cottage St, Winsted, CT 06098

      • 4 Beds
      • 4 Baths
      • 2,674 Sq Ft
      • Built 1890
      19 Cottage St, Winsted, CT 06098

      Last Sold Summary

      • 100 Days On Market

  • /38

    $345,000

    Under Contract
    • 5 Beds
    • 3 Baths
    • 2,602 Sq Ft

    63 Meadow St, Winsted, CT 06098

    Discover 63 Meadow, a turnkey 3-unit asset where thoughtful updates, strong rental performance, and a prime location come together to prove a high confidence investment opportunity. The property offers three well-proportioned units, a two-car attached garage, off-street parking spaces, and shared outdoor area that tenants appreciate. The current owner continued to elevate the building's value and

    Lauren Hill Mark Tavares Realty, LLC

    63 Meadow St, Winsted, CT 06098
  • 674 E Wakefield Blvd, Winsted, CT 06098

    $1,050,000

    Sold Jun 18, 2026

    674 E Wakefield Blvd, Winsted, CT 06098

    • 3 Beds
    • 3 Baths
    • 2,097 Sq Ft
    • Built 1942

    Last Sold Summary

    • 6% Above List Price
    • $501/SF
    • 13 Days On Market

    Current Estimated Value $913,683

    Last Listing Agent Patrick Smith Smith & DeGroat Real Estate

    674 E Wakefield Blvd, Winsted, CT 06098
  • /38

    $749,000

    $20K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,265 Sq Ft

    121 W Wakefield Blvd, Winsted, CT 06098

    Discover unparalleled Highland Lake living with this exceptional 1.00-acre retreat, boasting 50 feet of direct lake frontage and a newly renovated dock/deck. Enjoy breathtaking water views from your sunroom, dining room, and multiple bedrooms within this versatile 4/5 bedroom home. A unique first-floor suite with a separate exterior entrance offers ideal flexibility as a main-floor master or

    Elizabeth Stockwell Coldwell Banker Realty

    121 W Wakefield Blvd, Winsted, CT 06098
  • 160 Walnut St, Winsted, CT 06098

    $320,000

    Sold Oct 21, 2025

    160 Walnut St, Winsted, CT 06098

    • 3 Beds
    • 1.5 Baths
    • 1,674 Sq Ft
    • Built 1950

    Last Sold Summary

    • 11% Above List Price
    • $191/SF
    • 11 Days On Market

    Current Estimated Value $319,011

    Last Listing Agent Jeremy Beamer Eagle Eye Realty PLLC

    160 Walnut St, Winsted, CT 06098
  • 44 Lewis St, Winsted, CT 06098

    $335,000

    Sold Apr 07, 2026

    44 Lewis St, Winsted, CT 06098

    • 3 Beds
    • 2 Baths
    • 1,604 Sq Ft
    • Built 1980

    Last Sold Summary

    • 20% Above List Price
    • $209/SF
    • 48 Days On Market

    Current Estimated Value $320,961

    Last Listing Agent David Sartirana Northwest CT Realty

    44 Lewis St, Winsted, CT 06098
  • 111 Riverton Rd Unit 90, Winsted, CT 06098

    $171,000

    Sold Dec 30, 2025

    111 Riverton Rd Unit 90, Winsted, CT 06098

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

    Last Sold Summary

    • 14% Below List Price
    • $142/SF
    • 73 Days On Market

    Current Estimated Value $178,684

    Last Listing Agent David Sartirana Northwest CT Realty

    111 Riverton Rd Unit 90, Winsted, CT 06098
  • 107 Birdsall St, Winsted, CT 06098

    $210,000

    Sold Jul 02, 2026

    107 Birdsall St, Winsted, CT 06098

    • 4 Beds
    • 2 Baths
    • 1,874 Sq Ft
    • Built 1879

    Last Sold Summary

    • 16% Below List Price
    • $112/SF
    • 153 Days On Market

    Current Estimated Value $243,964

    Last Listing Agent Jesica Beaulieu Dave Jones Realty, LLC

    107 Birdsall St, Winsted, CT 06098
  • 29 Walnut St, Winsted, CT 06098

    $321,000

    Sold Aug 25, 2025

    29 Walnut St, Winsted, CT 06098

    • 3 Beds
    • 5 Baths
    • 2,623 Sq Ft
    • Built 1900

    Last Sold Summary

    • 4% Above List Price
    • $122/SF
    • 7 Days On Market

    Current Estimated Value $329,370

    Last Listing Agent Rosemary Scanlon Coldwell Banker Realty

    29 Walnut St, Winsted, CT 06098
    • 27 Benton St, Winsted, CT 06098

      Est $264,343

      Not Listed For Sale

      27 Benton St, Winsted, CT 06098

      • 2 Beds
      • 1.5 Baths
      • 1,109 Sq Ft
      • Built 1962
      27 Benton St, Winsted, CT 06098

      Last Sold Summary

      • 107 Days On Market

  • 208 Spencer Hill Rd, Winsted, CT 06098

    $385,000

    Sold Jan 22, 2026

    208 Spencer Hill Rd, Winsted, CT 06098

    • 3 Beds
    • 1.5 Baths
    • 1,969 Sq Ft
    • Built 1945

    Last Sold Summary

    • 4% Below List Price
    • $196/SF
    • 13 Days On Market

    Current Estimated Value $386,785

    Last Listing Agent David Sartirana Northwest CT Realty

    208 Spencer Hill Rd, Winsted, CT 06098
  • 123 Old North Rd, Winsted, CT 06098

    $475,000

    Sold May 22, 2026

    123 Old North Rd, Winsted, CT 06098

    • 3 Beds
    • 2 Baths
    • 1,781 Sq Ft
    • Built 1987

    Last Sold Summary

    • 12% Above List Price
    • $267/SF
    • 2 Days On Market

    Current Estimated Value $427,178

    Last Listing Agent Rick Berkenstock CENTURY 21 AllPoints Realty

    123 Old North Rd, Winsted, CT 06098
    • 98 Meadow St, Winsted, CT 06098

      Est $265,353

      Not Listed For Sale

      98 Meadow St, Winsted, CT 06098

      • 4 Beds
      • 2 Baths
      • 2,006 Sq Ft
      • Built 1870
      98 Meadow St, Winsted, CT 06098

      Last Sold Summary

      • 127 Days On Market

  • 123 Wetmore Ave, Winsted, CT 06098

    $330,000

    Sold Feb 27, 2026

    123 Wetmore Ave, Winsted, CT 06098

    • 4 Beds
    • 2 Baths
    • 2,345 Sq Ft
    • Built 1900

    Last Sold Summary

    • 3% Below List Price
    • $141/SF
    • 37 Days On Market

    Current Estimated Value $326,755

    Last Listing Agent Christine Hunter Hunter Real Estate, LLC

    123 Wetmore Ave, Winsted, CT 06098
  • 34 Hannifin Rd, Winsted, CT 06098

    $110,000

    Sold Jun 19, 2026

    34 Hannifin Rd, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 1,435 Sq Ft
    • Built 1850

    Last Sold Summary

    • 29% Above List Price
    • $77/SF
    • 39 Days On Market

    Current Estimated Value $256,145

    Last Listing Agent Michael Barnes Coldwell Banker Realty

    34 Hannifin Rd, Winsted, CT 06098
  • 10 Crescent St, Winsted, CT 06098

    $280,000

    Sold Jan 07, 2026

    10 Crescent St, Winsted, CT 06098

    • 4 Beds
    • 2 Baths
    • 2,444 Sq Ft
    • Built 1900

    Last Sold Summary

    • 8% Above List Price
    • $115/SF
    • 10 Days On Market

    Current Estimated Value $268,993

    Last Listing Agent Thomas Mele Social & Co Realty

    10 Crescent St, Winsted, CT 06098
    • 39 Finn St, Winsted, CT 06098

      Est $253,431

      Not Listed For Sale

      39 Finn St, Winsted, CT 06098

      • 3 Beds
      • 1 Bath
      • 1,175 Sq Ft
      • Built 1880
      39 Finn St, Winsted, CT 06098

      Last Sold Summary

      • 35 Days On Market

  • 430 Smith Hill Rd, Colebrook, CT 06021

    $425,000

    Sold Feb 26, 2026

    430 Smith Hill Rd, Colebrook, CT 06021

    • Land
    • 160 Acres
    • $2,656 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 188 Days On Market

    Last Listing Agent Rodney Motta Berkshire Hathaway NE Prop.

    430 Smith Hill Rd, Colebrook, CT 06021
  • 711 W Wakefield Blvd, Winchester Center, CT 06098

    $281,000

    Sold Aug 13, 2025

    711 W Wakefield Blvd, Winchester Center, CT 06098

    • Land
    • 26,571 Sq Ft
    • $460,656 per Acre

    Last Sold Summary

    • 12% Below List Price
    • 371 Days On Market

    Current Estimated Value $703,000

    Last Listing Agent Peter Kores The Washington Agency

    711 W Wakefield Blvd, Winchester Center, CT 06098
  • 22 Stanton Ave, Winsted, CT 06098

    $270,000

    Sold Sep 25, 2025

    22 Stanton Ave, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 1,058 Sq Ft
    • Built 1900

    Last Sold Summary

    • 2% Above List Price
    • $255/SF
    • 25 Days On Market

    Current Estimated Value $266,413

    Last Listing Agent Jeffrey Liskin Northwest CT Realty

    22 Stanton Ave, Winsted, CT 06098
  • 21 Riveredge Dr Unit 21, Winsted, CT 06098

    $160,000

    Sold Mar 10, 2026

    21 Riveredge Dr Unit 21, Winsted, CT 06098

    • 2 Beds
    • 1.5 Baths
    • 992 Sq Ft
    • Built 1986

    Last Sold Summary

    • 6% Below List Price
    • $161/SF
    • 19 Days On Market

    Current Estimated Value $160,735

    Last Listing Agent Jennifer Mitchell Northwest CT Realty

    21 Riveredge Dr Unit 21, Winsted, CT 06098
  • 817 E Wakefield Blvd, Winsted, CT 06098

    $231,000

    Sold Feb 20, 2026

    817 E Wakefield Blvd, Winsted, CT 06098

    • 2 Beds
    • 1 Bath
    • 1,051 Sq Ft
    • Built 1930

    Last Sold Summary

    • 3% Above List Price
    • $220/SF
    • 53 Days On Market

    Current Estimated Value $315,000

    Last Listing Agent George Sznaj DB Associates of CT, LLC

    817 E Wakefield Blvd, Winsted, CT 06098
  • 415 N Main St, Winsted, CT 06098

    $172,500

    Sold Aug 25, 2025

    415 N Main St, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 1,446 Sq Ft
    • Built 1900

    Last Sold Summary

    • 11% Below List Price
    • $119/SF
    • 43 Days On Market

    Current Estimated Value $193,203

    Last Listing Agent Jeffrey Liskin Northwest CT Realty

    415 N Main St, Winsted, CT 06098
  • 50 Manchester Heights, Winsted, CT 06098

    $330,000

    Sold Sep 24, 2025

    50 Manchester Heights, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 1,287 Sq Ft
    • Built 1953

    Last Sold Summary

    • 1% Below List Price
    • $256/SF
    • 118 Days On Market

    Current Estimated Value $315,585

    Last Listing Agent Lisa Bredice Coldwell Banker Realty

    50 Manchester Heights, Winsted, CT 06098

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