5,004

Winchester, CT Homes

Section Image
  • -00 Colebrook Rd, Colebrook, CT 06021
    -00 Colebrook Rd, Colebrook, CT 06021
    -00 Colebrook Rd, Colebrook, CT 06021
    /3

    $79,900

    • Land
    • 1.32 Acres
    • $60,530 per Acre

    -00 Colebrook Rd, Colebrook, CT 06021

    Set in the quiet beauty of Colebrook, this 1.32-acre approved building lot offers an excellent opportunity to bring your new home plans to life. Much of the early groundwork has already been completed, including a perc test, survey, driveway plan, septic design, and approvals for up to a 4-bedroom home, helping streamline the path from concept to construction. The lot has been cleared, offering a

    Steve Howey Coldwell Banker Realty

    -00 Colebrook Rd, Colebrook, CT 06021
  • 68 Wetmore Ave, Winsted, CT 06098

    $387,500

    Sold Jul 21, 2026

    68 Wetmore Ave, Winsted, CT 06098

    • 6 Beds
    • 2.5 Baths
    • 2,555 Sq Ft
    • Built 1900

    Last Sold Summary

    • 11% Above List Price
    • $152/SF
    • 60 Days On Market

    Current Estimated Value $308,864

    Last Listing Agent Alex King Lock and Key Realty, Inc

    68 Wetmore Ave, Winsted, CT 06098
    • 111 Riverton Rd Unit 66, Winsted, CT 06098

      Est $204,559

      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

      • 0 Days On Market

      Last Listing Agent Amy Sartirana Northwest CT Realty

  • 469 Platt Hill Rd, Winsted, CT 06098
    469 Platt Hill Rd, Winsted, CT 06098
    469 Platt Hill Rd, Winsted, CT 06098
    /40

    $895,000

    • 4 Beds
    • 2 Baths
    • 3,088 Sq Ft

    469 Platt Hill Rd, Winsted, CT 06098

    HOME-LAND -BARN. A TRUE NEW ENGLAND CLASSIC PROPERTY IN A POST CARD SETTING! For the Discerning Customer, whether You're an ANTIQUARIAN, HORSE & ANIMAL LOVER, or just seeking for a PEACEFUL & TRANQUIL LOCATION, this LITCHFIELD COUNTY HOME could possibly fit your Criteria. Stately 1789 , 11 Room 3,088 Sq. Ft. Colonial expresses Love, Warmth & Care. From the Solid Beams, Chestnut Wide-Board Floors,

    Marshall Cohen Cohen Agency

    469 Platt Hill Rd, Winsted, CT 06098
  • 111 Torringford St Unit 33, Winsted, CT 06098

    $204,000

    Sold Jun 15, 2026

    111 Torringford St Unit 33, Winsted, CT 06098

    • 2 Beds
    • 2 Baths
    • 1,102 Sq Ft
    • Built 1987

    Last Sold Summary

    • 7% Above List Price
    • $185/SF
    • 32 Days On Market

    Current Estimated Value $199,820

    Last Listing Agent Ryan Horvay Smith & DeGroat Real Estate

    111 Torringford St Unit 33, Winsted, CT 06098
    • 45 Beach St, Winsted, CT 06098

      Est $247,408

      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

      • 97 Days On Market

      Last Listing Agent Michael Barnes Coldwell Banker Realty

  • 0 Ashley Rd Unit Lot 6, Winchester, CT
    0 Ashley Rd Unit Lot 6, Winchester, CT
    0 Ashley Rd Unit Lot 6, Winchester, CT
    /19

    $150,000

    • Land
    • 6.18 Acres
    • $24,272 per Acre

    0 Ashley Rd Unit Lot 6, Winchester, CT

    Build Your Dream Retreat in Litchfield County! Escape the noise and pace of the city and discover 6.18 private wooded acres nestled in the scenic hills of Winchester, Connecticut. This approved 4-bedroom building lot offers the perfect opportunity to create a custom home or weekend retreat surrounded by nature, all within an easy drive of New York City and The Berkshires. Located just 200 yards

    Pascale Nejaime William Pitt Sotheby's Int'l

    0 Ashley Rd Unit Lot 6, Winchester, CT
  • 405 N Main St, Winsted, CT 06098

    $335,000

    Sold Jul 10, 2026

    405 N Main St, Winsted, CT 06098

    • 3 Beds
    • 1.5 Baths
    • 1,466 Sq Ft
    • Built 1890

    Last Sold Summary

    • 4% Below List Price
    • $229/SF
    • 4 Days On Market

    Current Estimated Value $340,615

    Last Listing Agent Nancy Reardon Berkshire Hathaway NE Prop.

    405 N Main St, Winsted, CT 06098
    • 193 Spencer Hill Rd, Winsted, CT 06098

      Est $413,609

      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

      • 57 Days On Market

      Last Listing Agent Victor Santana Santana Realty Group LLC

  • 624 Wynne Rd, Winsted, CT 06098
    624 Wynne Rd, Winsted, CT 06098
    624 Wynne Rd, Winsted, CT 06098
    /24

    $124,900

    $75K PRICE DROP Under Contract
    • Land
    • 5,227 Sq Ft
    • $1,040,833 per Acre

    624 Wynne Rd, Winsted, CT 06098

    Exceptional opportunity to build near one of Northwest Connecticut's most desirable lake communities. Just steps from beautiful Highland Lake, this water-view parcel offers the chance to create your dream home in a setting that combines lake lifestyle, natural beauty, and convenient access to some of Litchfield County's most sought-after destinations. Highland Lake is a true Connecticut gem-a

    AJ Davis Better Homes and Gardens Real Estate Executive Real Estate

    624 Wynne Rd, Winsted, CT 06098
  • 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 $274,542

    Last Listing Agent Jill Menard Realty One Group Cutting Edge

    115 Laurel Way, Winsted, CT 06098
    • 160 Hinsdale Ave, Winsted, CT 06098

      Est $345,102

      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

      • 46 Days On Market

      Last Listing Agent Laura Krzewski Realtor Bolanos & Associates LLC

  • 605 E Wakefield Blvd, Winchester, CT 06098
    605 E Wakefield Blvd, Winchester, CT 06098
    605 E Wakefield Blvd, Winchester, CT 06098
    /6

    $12,500

    Pending
    • Land
    • 10,018 Sq Ft
    • $54,348 per Acre

    605 E Wakefield Blvd, Winchester, CT 06098

    Across from the lake. Lot does not meet the set backs & is unbuildable.

    Diane Gombieski Carl Guild & Associates

    605 E Wakefield Blvd, Winchester, CT 06098
  • 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
    • 234 Oak St, Winsted, CT 06098

      Est $283,190

      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

      • 29 Days On Market

      Last Listing Agent Timothy McGrane Berkshire Hathaway NE Prop.

  • 44 Pine Rd, Colebrook, CT 06021
    44 Pine Rd, Colebrook, CT 06021
    44 Pine Rd, Colebrook, CT 06021
    /40

    $715,000

    $20K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,158 Sq Ft

    44 Pine Rd, Colebrook, CT 06021

    Enjoy exceptional privacy and peaceful country living in this spacious 4 bedroom, 2.5 bath contemporary Cape set atop a long winding driveway surrounded by natural beauty. The open floor plan on the main level offers comfortable living and entertaining spaces, including an updated eat in kitchen with stainless steel appliances, a dining room with a cozy wood burning fireplace, a generous living

    Mike Gregor Cohen Agency SiM, LLC

    44 Pine Rd, Colebrook, CT 06021
  • 736 W Wakefield Blvd, Winsted, CT 06098

    $525,000

    Sold Jul 21, 2026

    736 W Wakefield Blvd, Winsted, CT 06098

    • 1 Bed
    • 1.5 Baths
    • 1,308 Sq Ft
    • Built 1913

    Last Sold Summary

    • 3% Below List Price
    • $401/SF
    • 51 Days On Market

    Current Estimated Value $532,927

    Last Listing Agent Ed Richman Lakefront Living Realty, LLC

    736 W Wakefield Blvd, Winsted, CT 06098
    • 284 Gilbert Ave, Winsted, CT 06098

      Est $356,826

      Not Listed For Sale

      284 Gilbert Ave, Winsted, CT 06098

      • 4 Beds
      • 1 Bath
      • 1,849 Sq Ft
      • Built 1956
      284 Gilbert Ave, Winsted, CT 06098

      Last Sold Summary

      • 40 Days On Market

      Last Listing Agent David Sartirana Northwest CT Realty

  • 32 Norfolk Rd, Winchester, CT 06098
    32 Norfolk Rd, Winchester, CT 06098
    /2

    $299,900

    Pending
    • Land
    • 63 Acres
    • $4,760 per Acre

    32 Norfolk Rd, Winchester, CT 06098

    63-Acre Rural Retreat Abutting Algonquin State Forest - A Nature Lover's Dream! Discover the perfect blend of seclusion and accessibility with this 63-acre wooded paradise, directly abutting Algonquin State Forest. Located on a state highway and directly across from a scenic dry dam, this unique parcel provides endless possibilities-whether you're looking to build your dream home, start a hunting

    David D'Amore Northwest CT Realty

    32 Norfolk Rd, Winchester, CT 06098
  • 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 $210,208

    Last Listing Agent Bethany Lydem Stone Crest Realty LLC

    111 Riverton Rd Unit 61, Winsted, CT 06098
    • 24 Union St, Winsted, CT 06098

      Est $296,565

      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

      • 47 Days On Market

      Last Listing Agent Farzaneh RE/MAX Alliance

  • 00 Ramsgate Ln, Barkhamsted, CT 06063
    00 Ramsgate Ln, Barkhamsted, CT 06063
    /2

    $299,899

    • 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
  • 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 $328,051

    Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

    279 Pratt St, Winsted, CT 06098
    • 323 E Wakefield Blvd, Winsted, CT 06098

      Est $418,975

      Not Listed For Sale

      323 E Wakefield Blvd, Winsted, CT 06098

      • 3 Beds
      • 2.5 Baths
      • 1,426 Sq Ft
      • Built 1989
      323 E Wakefield Blvd, Winsted, CT 06098

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Heather Crabtree RE/MAX RISE

  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /26

    $239,000

    • 7 Beds
    • 3 Baths
    • 2,400 Sq Ft

    Unlisted Address

    Brand new to the market. Must see large 2 story Colonial featuring 13 rooms, 7 Bedrooms, 3 Bathrooms, Walk up attic and full basement. Includes a 2 story barn. Convenient location in the heart of town lends itself to easy access to many nearby amenities. As an investment this residence also has great potential to convert to a multi family home or could be renovated for commercial office space.

    Frank J. Berg Broker/Owner Town & Country Real Estate

    Unlisted Address
  • 94 Holabird Ave, Winsted, CT 06098

    $255,000

    Sold May 08, 2026

    94 Holabird Ave, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 1,422 Sq Ft
    • Built 1942

    Last Sold Summary

    • 2% Above List Price
    • $179/SF
    • 47 Days On Market

    Current Estimated Value $255,301

    Last Listing Agent Rob Rosa Berkshire Hathaway NE Prop.

    94 Holabird Ave, 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

      • 36 Days On Market

      Last Listing Agent Kirk Coates Luxe Estates, Inc

  • 119 W Wakefield Blvd, Winsted, CT 06098
    119 W Wakefield Blvd, Winsted, CT 06098
    119 W Wakefield Blvd, Winsted, CT 06098
    /35

    $849,900

    • 4 Beds
    • 2 Baths
    • 1,781 Sq Ft

    119 W Wakefield Blvd, Winsted, CT 06098

    Have you been dreaming of breathtaking lake views and a property that is truly special, unique, and turn-key? This exceptional home includes 50 feet of waterfront access with a boat dock and lift, making it a dream for lake enthusiasts! Nestled across from the tranquil First Bay, this beautifully renovated two-family home can be enjoyed as a single-family retreat or an income-generating

    Mela Veltri Case KW Legacy Partners

    119 W Wakefield Blvd, Winsted, CT 06098
  • 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 $334,049

    Last Listing Agent Mary Mary LeBlanc Realty

    41 Lovely St, Winsted, CT 06098
    • 42 Upland Rd, Winsted, CT 06098

      Est $247,310

      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

      • 71 Days On Market

      Last Listing Agent Glenn Kohrs Coldwell Banker Realty

  • 720 Main St, Winsted, CT 06098
    720 Main St, Winsted, CT 06098
    720 Main St, Winsted, CT 06098
    /24

    $395,000

    • 3 Beds
    • 2 Baths
    • 1,909 Sq Ft

    720 Main St, Winsted, CT 06098

    Where Opportunity Meets Lifestyle! Unlock the potential of this exceptional mixed-use property located in the heart of downtown Winsted. Positioned on a bustling Main Street with excellent exposure and constant pedestrian traffic, this property is an outstanding opportunity for entrepreneurs, investors, or anyone looking to combine business ownership with residential living. The street-level

    Arlene Gonzalez The Gonzalez Property Group

    720 Main St, Winsted, CT 06098
  • 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 $393,501

    Last Listing Agent Lana Van Valkenburgh Vision Real Estate

    166 Torringford St, Winsted, CT 06098
    • 125 E Mountain Ave, Winsted, CT 06098

      Est $337,755

      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

      • 39 Days On Market

      Last Listing Agent David Sartirana Northwest CT Realty

  • 118 Meadow St, Winsted, CT 06098
    118 Meadow St, Winsted, CT 06098
    118 Meadow St, Winsted, CT 06098
    /31

    $269,999

    $20K PRICE DROP 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
  • 878 W Wakefield Blvd, Winsted, CT 06098

    $1,200,000

    Sold Jul 07, 2026

    878 W Wakefield Blvd, Winsted, CT 06098

    • 4 Beds
    • 3 Baths
    • 3,330 Sq Ft
    • Built 1973

    Last Sold Summary

    • 20% Above List Price
    • $360/SF
    • 7 Days On Market

    Current Estimated Value $983,110

    Last Listing Agent Annie Q Simard LPT Realty

    878 W Wakefield Blvd, Winsted, CT 06098
    • 103 E Mountain Ave, Winsted, CT 06098

      Est $295,977

      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

      • 29 Days On Market

      Last Listing Agent David Merrigan Merrigan & Lefebvre Realty

  • 147 E Wakefield Blvd, Winsted, CT 06098
    147 E Wakefield Blvd, Winsted, CT 06098
    147 E Wakefield Blvd, Winsted, CT 06098
    /29

    $269,900

    $30K PRICE DROP Under Contract
    • 2 Beds
    • 1 Bath
    • 702 Sq Ft

    147 E Wakefield Blvd, Winsted, CT 06098

    Come enjoy Highland Lake living just in time for Summer. Relax in this one level living, cozy cottage home with views of the lake from your deck and just a short distance to Resha beach. Enter through a large mudroom to your open living room with large window to let in natural light, updated kitchen, 2 bedrooms, 1 full bath, main level laundry, front and rear deck, large yard & shed. New flooring

    Mary Mary LeBlanc Realty

    147 E Wakefield Blvd, Winsted, CT 06098
  • 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
    • 129 Forest Ave, Winsted, CT 06098

      Est $665,985

      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

      • 195 Days On Market

      Last Listing Agent Daniel Burgio William Raveis Real Estate

  • 431 W Wakefield Blvd, Winsted, CT 06098
    431 W Wakefield Blvd, Winsted, CT 06098
    431 W Wakefield Blvd, Winsted, CT 06098
    /37

    $1,850,000

    Pending
    • 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

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