5,115

Winchester, CT Homes

Section Image
  • 9 Loomis St, Winsted, CT 06098

    $144,000 Sold May 29, 2025

    9 Loomis St, Winsted, CT 06098

    • 3 Beds
    • 2 Baths
    • 1,768 Sq Ft
    • Built 1910

    Last Sold Summary

    • 28% Below List Price
    • $81/SF
    • 18 Days On Market

    Current Estimated Value $151,214

    Last Listing Agent Kristen Duchene Litchfield County Real Estate

    9 Loomis St, Winsted, CT 06098
    • 3 Brookside Ave, Winsted, CT 06098

      Est $232,952 Not Listed For Sale

      3 Brookside Ave, Winsted, CT 06098

      • 6 Beds
      • 2,421 Sq Ft
      • Built 1900
      3 Brookside Ave, Winsted, CT 06098

      Last Sold Summary

      • 37% Above List Price
      • $70/SF
      • 78 Days On Market

      Last Sold Price $170,000

      Last Listing Agent Jayson Kemp Five Stars Realty

  • /2

    $299,900

    • Land
    • 34 Acres
    • $8,821 per Acre

    00 Ramsgate Ln, Barkhamsted, CT 06063

    30 +/- acres in ideal location in Barkhamsted bordering American Legion State Forest in the rear. Minutes from historic Riverton Center and world-renowned fly fishing. Many outdoor activities close by including hiking, biking, tubing, skiing, boating and many more. Land is ideal for almost any application, subdividing, recreation, horses, etc. Land will be subdivided upon contract and prior to

    Heidi Picard-Ramsay Berkshire Hathaway NE Prop.

    00 Ramsgate Ln, Barkhamsted, CT 06063
  • 131 Willow St, Winsted, CT 06098

    $293,000 Sold Oct 30, 2025

    131 Willow St, Winsted, CT 06098

    • 6 Beds
    • 2 Baths
    • 2,160 Sq Ft
    • Built 1900

    Last Sold Summary

    • 2% Below List Price
    • $136/SF
    • 83 Days On Market

    Last Listing Agent Amanda Balaski Northwest CT Realty

    131 Willow St, Winsted, CT 06098
    • 111 Riverton Rd Unit 66, Winsted, CT 06098

      Est $198,847 Not Listed For Sale

      111 Riverton Rd Unit 66, Winsted, CT 06098

      • 2 Beds
      • 1.5 Baths
      • 1,204 Sq Ft
      • Built 1987
      111 Riverton Rd Unit 66, Winsted, CT 06098

      Last Sold Summary

      • 11% Above List Price
      • $149/SF
      • 0 Days On Market

      Last Sold Price $179,900

      Last Listing Agent Amy Sartirana Northwest CT Realty

  • /27

    $375,000 Pending

    • 3 Beds
    • 3,660 Sq Ft

    57 Main St, Winsted, CT 06098

    Wonderful multiuse property on Main St. in Winsted. Currently used as a cleaners on the first floor and residential unit on the second floor. Multiple possibilities for this building which is in a prime location. Potential to take over the current business and rent or live in second floor, covert to multifamily or start a new business venture. This property is also listed as commercial with MLS

    Stacy LaQuerre Regall Realty, LLC

    57 Main St, Winsted, CT 06098
  • 17 Adams St, Winsted, CT 06098

    $315,000 Sold Sep 29, 2025

    17 Adams St, Winsted, CT 06098

    • 3 Beds
    • 1.5 Baths
    • 1,747 Sq Ft
    • Built 1900

    Last Sold Summary

    • 5% Above List Price
    • $180/SF
    • 85 Days On Market

    Current Estimated Value $314,065

    Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

    17 Adams St, Winsted, CT 06098
    • 45 Beach St, Winsted, CT 06098

      Est $251,270 Not Listed For Sale

      45 Beach St, Winsted, CT 06098

      • 4 Beds
      • 2 Baths
      • 2,076 Sq Ft
      • Built 1900
      45 Beach St, Winsted, CT 06098

      Last Sold Summary

      • 56% Above List Price
      • $78/SF
      • 97 Days On Market

      Last Sold Price $161,500

      Last Listing Agent Michael Barnes Coldwell Banker Realty

  • /31

    $269,999 Pending

    • 3 Beds
    • 2 Baths
    • 1,652 Sq Ft

    118 Meadow St, Winsted, CT 06098

    This charming historic home, built in 1860, blends timeless character with thoughtful updates. Featuring 3-4 bedrooms, this property offers flexible living space to meet your needs. The beautifully remodeled upstairs bathroom is a standout feature, offering modern comfort within this classic home. Enjoy your LARGE eat-in kitchen with laundry hook ups and plenty of natural lighting and ample

    Ashley Henry The Washington Agency

    118 Meadow St, Winsted, CT 06098
  • 0 Platt Hill Rd Unit 24079213, Winsted, CT 06098

    $85,000 Sold Mar 27, 2025

    0 Platt Hill Rd Unit 24079213, Winsted, CT 06098

    • Land
    • 3.06 Acres
    • $27,742 per Acre

    Last Sold Summary

    • 21% Above List Price
    • 5 Days On Market

    Last Listing Agent Nadia Corvo Northwest CT Realty

    0 Platt Hill Rd Unit 24079213, Winsted, CT 06098
    • 193 Spencer Hill Rd, Winsted, CT 06098

      Est $421,983 Not Listed For Sale

      193 Spencer Hill Rd, Winsted, CT 06098

      • 4 Beds
      • 2.5 Baths
      • 2,313 Sq Ft
      • Built 2012
      193 Spencer Hill Rd, Winsted, CT 06098

      Last Sold Summary

      • 46% Above List Price
      • $125/SF
      • 57 Days On Market

      Last Sold Price $290,000

      Last Listing Agent Victor Santana Santana Realty Group LLC

  • /23

    $274,900 Under Contract

    • 3 Beds
    • 1.5 Baths
    • 1,267 Sq Ft

    9 Central Ave, Winsted, CT 06098

    Welcome to this adorable, solidly built Cape in the heart of Winchester, Connecticut-where home is more than just a place, it's a way of life. Nestled in the scenic Litchfield Hills, Winchester is a community full of character, rich history, and strong local businesses, offering a wonderful quality of life. From excellent schools and charming downtown shops to beautiful lakes and outdoor

    Suzie Larson Turning Point Realty, LLC

    9 Central Ave, Winsted, CT 06098
  • 325 E Wakefield Blvd, Winsted, CT 06098

    $270,000 Sold Mar 31, 2025

    325 E Wakefield Blvd, Winsted, CT 06098

    • 2 Beds
    • 1.5 Baths
    • 1,192 Sq Ft
    • Built 1930

    Last Sold Summary

    • 4% Above List Price
    • $227/SF
    • 39 Days On Market

    Current Estimated Value $286,927

    Last Listing Agent Brigitte Richter William Pitt Sotheby's Int'l

    325 E Wakefield Blvd, Winsted, CT 06098
    • 160 Hinsdale Ave, Winsted, CT 06098

      Est $344,333 Not Listed For Sale

      160 Hinsdale Ave, Winsted, CT 06098

      • 4 Beds
      • 1.5 Baths
      • 2,379 Sq Ft
      • Built 1930
      160 Hinsdale Ave, Winsted, CT 06098

      Last Sold Summary

      • 2% Below List Price
      • $147/SF
      • 46 Days On Market

      Last Sold Price $350,000

      Last Listing Agent Laura Krzewski Realtor Bolanos & Associates LLC

  • /36

    $1,850,000

    • 9 Beds
    • 5.5 Baths
    • 7,000 Sq Ft

    431 W Wakefield Blvd, Winsted, CT 06098

    Live the Highland Lake Dream - 431 W. Wakefield Blvd, Winchester, CT Summer is just around the corner - and in Winsted, resort living never ends. Recently named one of the most desirable towns to live in, with the breathtaking Highland Lake at its heart, Winchester offers the perfect blend of beauty and lifestyle. This waterfront estate at 431 W. Wakefield Blvd isn't just a home - it's your

    Lisa Ogren Berkshire Hathaway NE Prop.

    431 W Wakefield Blvd, Winsted, CT 06098
  • 22 Curtice St, Winsted, CT 06098

    $243,000 Sold Nov 17, 2025

    22 Curtice St, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 1,334 Sq Ft
    • Built 1900

    Last Sold Summary

    • $182/SF
    • 33 Days On Market

    Current Estimated Value $244,150

    Last Listing Agent Terence Dominick Exceptional Real Estate LLC

    22 Curtice St, Winsted, CT 06098
    • 234 Oak St, Winsted, CT 06098

      Est $251,790 Not Listed For Sale

      234 Oak St, Winsted, CT 06098

      • 3 Beds
      • 2 Baths
      • 1,302 Sq Ft
      • Built 1890
      234 Oak St, Winsted, CT 06098

      Last Sold Summary

      • 7% Above List Price
      • $180/SF
      • 29 Days On Market

      Last Sold Price $235,000

      Last Listing Agent Timothy McGrane Berkshire Hathaway Home Services

  • /9

    $850,000

    • Land
    • 116.5 Acres
    • $7,296 per Acre

    82 Riverton Rd, Colebrook, CT 06021

    Escape to Your Own 116 acres of Paradise in Colebrook, CT! Discover 116 +/- acres of picturesque land nestled along Riverton Road in the heart of scenic Colebrook, Connecticut. This extraordinary property offers a rare opportunity to own a vast expanse of rural beauty, complete with two serene ponds, winding old logging roads, and a mix of standing hardwoods and softwoods that create a lush,

    Suzie Larson Turning Point Realty, LLC

    82 Riverton Rd, Colebrook, CT 06021
  • 115 Laurel Way, Winsted, CT 06098

    $261,000 Sold Oct 17, 2025

    115 Laurel Way, Winsted, CT 06098

    • 1 Bed
    • 1 Bath
    • 604 Sq Ft
    • Built 1940

    Last Sold Summary

    • 4% Above List Price
    • $432/SF
    • 9 Days On Market

    Current Estimated Value $250,380

    Last Listing Agent Jill Menard Realty One Group Cutting Edge

    115 Laurel Way, Winsted, CT 06098
    • 110 E Mountain Ave, Winsted, CT 06098

      Est $199,633 Not Listed For Sale

      110 E Mountain Ave, Winsted, CT 06098

      • 2 Beds
      • 1 Bath
      • 734 Sq Ft
      • Built 1945
      110 E Mountain Ave, Winsted, CT 06098

      Last Sold Summary

      • 60% Above List Price
      • $170/SF
      • 36 Days On Market

      Last Sold Price $125,000

      Last Listing Agent David D'Amore Northwest CT Realty

  • 174 Wallens St Unit D3, Winsted, CT 06098

    $260,000 Sold Sep 05, 2025

    174 Wallens St Unit D3, Winsted, CT 06098

    • 2 Beds
    • 2 Baths
    • 1,352 Sq Ft
    • Built 2005

    Last Sold Summary

    • 6% Above List Price
    • $192/SF
    • 1 Day On Market

    Last Listing Agent Mary New Berkshire Hathaway NE Prop.

    174 Wallens St Unit D3, Winsted, CT 06098
    • 24 Union St, Winsted, CT 06098

      Est $266,094 Not Listed For Sale

      24 Union St, Winsted, CT 06098

      • 4 Beds
      • 2 Baths
      • 2,582 Sq Ft
      • Built 1895
      24 Union St, Winsted, CT 06098

      Last Sold Summary

      • 6% Above List Price
      • $97/SF
      • 47 Days On Market

      Last Sold Price $250,000

      Last Listing Agent Farzaneh RE/MAX

  • 111 Riverton Rd Unit 61, Winsted, CT 06098

    $194,900 Sold Dec 08, 2025

    111 Riverton Rd Unit 61, Winsted, CT 06098

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

    Last Sold Summary

    • 5% Below List Price
    • $162/SF
    • 61 Days On Market

    Current Estimated Value $197,374

    Last Listing Agent Bethany Lydem Stone Crest Realty LLC

    111 Riverton Rd Unit 61, Winsted, CT 06098
    • 174 Wallens St Unit C7, Winsted, CT 06098

      Not Listed For Sale

      174 Wallens St Unit C7, Winsted, CT 06098

      • 1 Bed
      • 2 Baths
      • 1,334 Sq Ft
      • Built 2005
      174 Wallens St Unit C7, Winsted, CT 06098

      Last Sold Summary

      • 7% Above List Price
      • $165/SF
      • 36 Days On Market

      Last Sold Price $220,000

      Last Listing Agent Kirk Coates Luxe Estates, Inc

  • 279 Pratt St, Winsted, CT 06098

    $290,000 Sold Aug 28, 2025

    279 Pratt St, Winsted, CT 06098

    • 4 Beds
    • 1 Bath
    • 1,978 Sq Ft
    • Built 1880

    Last Sold Summary

    • 24% Below List Price
    • $147/SF
    • 49 Days On Market

    Current Estimated Value $305,222

    Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

    279 Pratt St, Winsted, CT 06098
    • 42 Upland Rd, Winsted, CT 06098

      Est $225,949 Not Listed For Sale

      42 Upland Rd, Winsted, CT 06098

      • 2 Beds
      • 1 Bath
      • 1,236 Sq Ft
      • Built 1891
      42 Upland Rd, Winsted, CT 06098

      Last Sold Summary

      • 8% Above List Price
      • $169/SF
      • 71 Days On Market

      Last Sold Price $209,000

      Last Listing Agent Glenn Kohrs Coldwell Banker Realty

  • 493 N Main St, Winsted, CT 06098

    $275,000 Sold Apr 16, 2025

    493 N Main St, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 1,277 Sq Ft
    • Built 1940

    Last Sold Summary

    • 6% Above List Price
    • $215/SF
    • 114 Days On Market

    Current Estimated Value $284,891

    Last Listing Agent Jessica Sperry Maverick Realty

    493 N Main St, Winsted, CT 06098
    • 125 E Mountain Ave, Winsted, CT 06098

      Est $309,826 Not Listed For Sale

      125 E Mountain Ave, Winsted, CT 06098

      • 3 Beds
      • 2 Baths
      • 1,622 Sq Ft
      • Built 1953
      125 E Mountain Ave, Winsted, CT 06098

      Last Sold Summary

      • 11% Above List Price
      • $173/SF
      • 39 Days On Market

      Last Sold Price $280,000

      Last Listing Agent David Sartirana Northwest CT Realty

  • 102 Hollow Hill Rd, Winsted, CT 06098

    $639,000 Sold Jul 31, 2025

    102 Hollow Hill Rd, Winsted, CT 06098

    • 3 Beds
    • 2.5 Baths
    • 2,692 Sq Ft
    • Built 2004

    Last Sold Summary

    • 8% Above List Price
    • $237/SF
    • 49 Days On Market

    Current Estimated Value $653,199

    Last Listing Agent Dawn Rousseau Showcase Realty, Inc.

    102 Hollow Hill Rd, Winsted, CT 06098
    • 103 E Mountain Ave, Winsted, CT 06098

      Est $279,695 Not Listed For Sale

      103 E Mountain Ave, Winsted, CT 06098

      • 3 Beds
      • 1 Bath
      • 1,304 Sq Ft
      • Built 1955
      103 E Mountain Ave, Winsted, CT 06098

      Last Sold Summary

      • 2% Above List Price
      • $211/SF
      • 29 Days On Market

      Last Sold Price $275,000

      Last Listing Agent David Merrigan Merrigan & Lefebvre Realty

  • 104 Norfolk Rd, Winsted, CT 06098

    $8,000 Sold May 16, 2025

    104 Norfolk Rd, Winsted, CT 06098

    • 2 Beds
    • 1 Bath
    • 980 Sq Ft
    • Built 1930

    Last Sold Summary

    • 79% Below List Price
    • $8/SF
    • 44 Days On Market

    Last Listing Agent David Sartirana Northwest CT Realty

    104 Norfolk Rd, Winsted, CT 06098
    • 129 Forest Ave, Winsted, CT 06098

      Est $626,951 Not Listed For Sale

      129 Forest Ave, Winsted, CT 06098

      • 3 Beds
      • 2.5 Baths
      • 2,400 Sq Ft
      • Built 2007
      129 Forest Ave, Winsted, CT 06098

      Last Sold Summary

      • 6% Below List Price
      • $279/SF
      • 195 Days On Market

      Last Sold Price $670,000

      Last Listing Agent Daniel Burgio William Raveis Real Estate

  • 41 Lovely St, Winsted, CT 06098

    $383,000 Sold Sep 10, 2025

    41 Lovely St, Winsted, CT 06098

    • 5 Beds
    • 2 Baths
    • 2,531 Sq Ft
    • Built 1910

    Last Sold Summary

    • 9% Above List Price
    • $151/SF
    • 39 Days On Market

    Current Estimated Value $379,121

    Last Listing Agent Mary Mary LeBlanc Realty

    41 Lovely St, Winsted, CT 06098
    • 143 Mountain Rd, Winsted, CT 06098

      Est $324,254 Not Listed For Sale

      143 Mountain Rd, Winsted, CT 06098

      • 2 Beds
      • 1 Bath
      • 1,249 Sq Ft
      • Built 1920
      143 Mountain Rd, Winsted, CT 06098

      Last Sold Summary

      • 16% Above List Price
      • $223/SF
      • 92 Days On Market

      Last Sold Price $279,000

      Last Listing Agent Don Sciarretto Berkshire Hathaway Home Services

  • 166 Torringford St, Winsted, CT 06098

    $370,000 Sold Nov 14, 2025

    166 Torringford St, Winsted, CT 06098

    • 3 Beds
    • 2 Baths
    • 2,024 Sq Ft
    • Built 1898

    Last Sold Summary

    • 3% Below List Price
    • $183/SF
    • 77 Days On Market

    Current Estimated Value $376,042

    Last Listing Agent Lana Van Valkenburgh Vision Real Estate

    166 Torringford St, Winsted, CT 06098
    • 11 Orchard St, Winsted, CT 06098

      Est $217,726 Not Listed For Sale

      11 Orchard St, Winsted, CT 06098

      • 3 Beds
      • 1 Bath
      • 1,759 Sq Ft
      • Built 1900
      11 Orchard St, Winsted, CT 06098

      Last Sold Summary

      • 33% Above List Price
      • $93/SF
      • 19 Days On Market

      Last Sold Price $164,000

      Last Listing Agent Jonathan Gineo Silver and Oak Realty

  • 27 Thibault Ave, Winsted, CT 06098

    $389,900 Sold Nov 06, 2025

    27 Thibault Ave, Winsted, CT 06098

    • 8 Beds
    • 5 Baths
    • 7,372 Sq Ft
    • Built 1900

    Last Sold Summary

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

    Last Listing Agent Cathy Macias Northwest CT Realty

    27 Thibault Ave, Winsted, CT 06098
    • 303 E Wakefield Blvd, Winsted, CT 06098

      Est $298,059 Not Listed For Sale

      303 E Wakefield Blvd, Winsted, CT 06098

      • 2 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1986
      303 E Wakefield Blvd, Winsted, CT 06098

      Last Sold Summary

      • 8% Above List Price
      • $286/SF
      • 21 Days On Market

      Last Sold Price $275,000

      Last Listing Agent Tammy Schaller William Raveis Real Estate

  • 409 N Main St, Winsted, CT 06098

    $388,000 Sold Aug 27, 2025

    409 N Main St, Winsted, CT 06098

    • 5 Beds
    • 2 Baths
    • 2,403 Sq Ft
    • Built 1868

    Last Sold Summary

    • $161/SF
    • 70 Days On Market

    Current Estimated Value $378,037

    Last Listing Agent Christine Hunter Hunter Real Estate, LLC

    409 N Main St, Winsted, CT 06098
    • 151 Hinsdale Ave, Winsted, CT 06098

      Est $271,717 Not Listed For Sale

      151 Hinsdale Ave, Winsted, CT 06098

      • 3 Beds
      • 2 Baths
      • 1,634 Sq Ft
      • Built 1948
      151 Hinsdale Ave, Winsted, CT 06098

      Last Sold Summary

      • 24% Above List Price
      • $135/SF
      • 154 Days On Market

      Last Sold Price $220,000

      Last Listing Agent Sarah Isabella Glenstone Real Estate LLC

Showing Results 121 - 160, Page 4 of 18

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