4,852

Winsted, CT Homes

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  • 7 Stadler Heights, Winsted, CT 06098
    7 Stadler Heights, Winsted, CT 06098
    7 Stadler Heights, Winsted, CT 06098
    /8

    $389,000

    • Land
    • 20.87 Acres
    • $18,639 per Acre

    7 Stadler Heights, Winsted, CT 06098

    Welcome, You be the first, to come and conquer this land here in Winchester, Connecticut. There are 20.87 acres of virgin land. Come and build, do what you do best, you can have Peace and Privacy!!! There are no sidewalks, no streets that drive through. You are 40 minutes from multiple private schools. 16 minutes from Charlotte Hungerford Hospital. 1 hour from Tweed Airport New Haven. 39 minutes

    Hector Ortiz KW Legacy Partners

    7 Stadler Heights, Winsted, CT 06098
  • 62 Fruit St Unit 64, Winsted, CT 06098

    $326,000

    Sold Oct 31, 2025

    62 Fruit St Unit 64, Winsted, CT 06098

    • 6 Beds
    • 2 Baths
    • 3,078 Sq Ft
    • Built 1902

    Last Sold Summary

    • $106/SF
    • 13 Days On Market

    Current Estimated Value $297,466

    Last Listing Agent Antonio De La Cruz Eagle Eye Realty PLLC

    62 Fruit St Unit 64, Winsted, CT 06098
  • 405 N Main St, Winsted, CT 06098
    405 N Main St, Winsted, CT 06098
    405 N Main St, Winsted, CT 06098
    /40

    $349,900

    Pending
    • 3 Beds
    • 1.5 Baths
    • 1,466 Sq Ft

    405 N Main St, Winsted, CT 06098

    Move right into this absolutely charming Colonial with incredible curb appeal & pride of ownership throughout! Lovingly maintained & impeccably clean, this true dollhouse is set on .31 acres in the scenic, beautiful Litchfield Hills & just minutes to Northwestern Community College, the town green, shopping, restaurants, walking trails, biking, & endless outdoor recreation. From the moment you

    Nancy Reardon Berkshire Hathaway NE Prop.

    405 N Main St, Winsted, CT 06098
  • 226 E Wakefield Blvd, Winsted, CT 06098

    $380,000

    Sold Sep 17, 2025

    226 E Wakefield Blvd, Winsted, CT 06098

    • 3 Beds
    • 1.5 Baths
    • 1,196 Sq Ft
    • Built 1974

    Last Sold Summary

    • 3% Above List Price
    • $318/SF
    • 38 Days On Market

    Current Estimated Value $378,003

    Last Listing Agent Pascale Nejaime William Pitt Sotheby's Int'l

    226 E Wakefield Blvd, Winsted, CT 06098
  • 736 W Wakefield Blvd, Winsted, CT 06098
    736 W Wakefield Blvd, Winsted, CT 06098
    736 W Wakefield Blvd, Winsted, CT 06098
    /24

    $544,000

    Under Contract
    • 1 Bed
    • 1.5 Baths
    • 1,308 Sq Ft

    736 W Wakefield Blvd, Winsted, CT 06098

    Welcome to "WatersEdge" a Seasonal Cottage perched on a landscaped hillside overlooking Third Bay of beautiful Highland Lake. Views Views Views! Highland is a fully recreational lake. On the main floor of the cottage you will find one bedroom, a bath with shower, a spacious family room with a stone fireplace, and an efficient kitchen with storage. The lower walk-out level can be accessed by the

    Ed Richman Lakefront Living Realty, LLC

    736 W Wakefield Blvd, Winsted, CT 06098
  • 343 W Wakefield Blvd, Winsted, CT 06098

    $236,434

    Sold Aug 25, 2025

    343 W Wakefield Blvd, Winsted, CT 06098

    • 2 Beds
    • 1 Bath
    • 674 Sq Ft
    • Built 1923

    Last Sold Summary

    • 15% Below List Price
    • $351/SF
    • 40 Days On Market

    Current Estimated Value $262,964

    Last Listing Agent Patrick Precourt Meridian Realty Group LLC

    343 W Wakefield Blvd, Winsted, CT 06098
  • 71-73 Wheeler St, Winchester, CT 06098
    71-73 Wheeler St, Winchester, CT 06098
    71-73 Wheeler St, Winchester, CT 06098
    /17

    $450,000

    Under Contract
    • 8 Beds
    • 4 Baths
    • 2,000 Sq Ft

    71-73 Wheeler St, Winchester, CT 06098

    A positive income even if you live in one of the units. Two 2 family homes(4 units total) on one parcel. Good parking. Large lot. Residential setting. Second floor of back house has a private deck, back yard and woods, yet is convenient to downtown. Highest and best offers must be submitted by 6/12/26 at 12pm.

    Ida Chaplinski The DIY Listing

    71-73 Wheeler St, Winchester, CT 06098
  • 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
  • 00 Main St, Winsted, CT 06098
    00 Main St, Winsted, CT 06098
    00 Main St, Winsted, CT 06098
    /6

    $386,000

    • Land
    • 1.91 Acres
    • $202,094 per Acre

    00 Main St, Winsted, CT 06098

    Exceptional 2+ Acre Development Opportunity - Route 44, Winsted, CT** Rare opportunity to acquire approximately 2+- acres with nearly 700 feet of frontage on Main Street (Route 44), one of Winsted's primary commercial corridors. Located within the Town Gateway Zone, this highly visible parcel offers outstanding flexibility for a variety of development opportunities, including commercial,

    Dan Merrigan Merrigan & Lefebvre Realty

    00 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 $310,769

    Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

    17 Adams St, Winsted, CT 06098
  • 748 Lake Dr, Winsted, CT 06098
    748 Lake Dr, Winsted, CT 06098
    748 Lake Dr, Winsted, CT 06098
    /40

    $1,249,900

    Pending
    • 5 Beds
    • 4 Baths
    • 3,584 Sq Ft

    748 Lake Dr, Winsted, CT 06098

    Rare opportunities like this do not come around often on Highland Lake! Located on the east side of 3rd bay, this unique waterfront property offers beautiful views and magnificent sunsets. This unique waterfront layout offers endless opportunities; from a family compound, multi generational living, guest space or a private lake retreat! Enjoy outdoor living on the massive deck, custom dock, and

    Ryan Horvay Smith & DeGroat Real Estate

    748 Lake Dr, Winsted, CT 06098
  • 257 Wallens Hill Rd, Winsted, CT 06098

    $550,000

    Sold Jul 01, 2026

    257 Wallens Hill Rd, Winsted, CT 06098

    • 3 Beds
    • 2.5 Baths
    • 2,011 Sq Ft
    • Built 1955

    Last Sold Summary

    • 2% Above List Price
    • $273/SF
    • 30 Days On Market

    Current Estimated Value $370,495

    Last Listing Agent Kelly Sullivan Sullivan Real Estate Inc

    257 Wallens Hill Rd, Winsted, CT 06098
    • 14 Hamill Dr, Winsted, CT 06098

      Est $260,615

      Not Listed For Sale

      14 Hamill Dr, Winsted, CT 06098

      • 3 Beds
      • 1.5 Baths
      • 1,888 Sq Ft
      • Built 1973
      14 Hamill Dr, Winsted, CT 06098

      Last Sold Summary

      • 27 Days On Market

  • 115 Old Robertsville Rd, Winsted, CT 06098
    115 Old Robertsville Rd, Winsted, CT 06098
    115 Old Robertsville Rd, Winsted, CT 06098
    /13

    $649,900

    Pending
    • Land
    • 41.23 Acres
    • $15,763 per Acre

    115 Old Robertsville Rd, Winsted, CT 06098

    Development Opportunity! 41.23 Acres with Historic Home & Barn - Subdivision Possible Rare chance to own a prime 41.23-acre parcel in New England with an 1800 Antique Colonial Farmhouse and classic English/New England hybrid barn. The land may be subdividable and is located near the highly desirable Riverwalk Condominiums, making it ideal for new condo development (subject to approvals). The home

    Jared Tedesco Litchfield County Real Estate

    115 Old Robertsville Rd, Winsted, CT 06098
  • 129 E Lake St, Winsted, CT 06098

    $1,475,000

    Sold Jun 09, 2026

    129 E Lake St, Winsted, CT 06098

    • 3 Beds
    • 3.5 Baths
    • 2,699 Sq Ft
    • Built 1910

    Last Sold Summary

    • 1% Below List Price
    • $546/SF
    • 12 Days On Market

    Current Estimated Value $1,438,024

    Last Listing Agent KAREN NEWTON William Pitt Sotheby's Int'l

    129 E Lake St, Winsted, CT 06098
    • 830 Main St, Winsted, CT 06098

      Est $216,196

      Not Listed For Sale

      830 Main St, Winsted, CT 06098

      • 5 Beds
      • 4 Baths
      • 3,115 Sq Ft
      • Built 1900
      830 Main St, Winsted, CT 06098

      Last Sold Summary

      • 14 Days On Market

  • 111 Moore Ave, Winsted, CT 06098
    111 Moore Ave, Winsted, CT 06098
    111 Moore Ave, Winsted, CT 06098
    /26

    $250,000

    Pending
    • 3 Beds
    • 1 Bath
    • 1,392 Sq Ft

    111 Moore Ave, Winsted, CT 06098

    *Deadline set of Tuesday 6/30 at Noon. Seller reserves the right to take an offer at anytime.* Nestled on a well maintained lot, this charming Cape offers the perfect balance of privacy and convenience. Set just off the beaten path, the property enjoys a peaceful, rural feel while remaining close to shopping, dining, and everyday amenities. Thoughtfully updated over the years, improvements

    Melanie LeRoy William Raveis Real Estate

    111 Moore Ave, Winsted, CT 06098
  • 90 Colony Dr, Winsted, CT 06098

    $325,000

    Sold Jun 10, 2026

    90 Colony Dr, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 1,282 Sq Ft
    • Built 1969

    Last Sold Summary

    • 7% Below List Price
    • $254/SF
    • 64 Days On Market

    Current Estimated Value $333,753

    Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

    90 Colony Dr, Winsted, CT 06098
    • 257 Walnut St, Winsted, CT 06098

      Est $288,751

      Not Listed For Sale

      257 Walnut St, Winsted, CT 06098

      • 3 Beds
      • 1.5 Baths
      • 1,490 Sq Ft
      • Built 1900
      257 Walnut St, Winsted, CT 06098

      Last Sold Summary

      • 21 Days On Market

  • 393 Winchester Rd, Winsted, CT 06098
    393 Winchester Rd, Winsted, CT 06098
    393 Winchester Rd, Winsted, CT 06098
    /5

    $295,000

    • Land
    • 51 Acres
    • $5,784 per Acre

    393 Winchester Rd, Winsted, CT 06098

    WINCHESTER CREST 51 acres of forested gently rolling land sited upland in Winchester Center. There is a former homesite and multiple choices for additional homesites affording complete privacy. There is abundant wildlife, trails, intermittent streams, dense and sparse forest. Perfect for year round home site, weekend retreat or recreational land.

    Tom McGowan Elyse Harney Real Estate

    393 Winchester Rd, 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 $243,963

    Last Listing Agent Terence Dominick Exceptional Real Estate LLC

    22 Curtice St, Winsted, CT 06098
  • 660 E Wakefield Blvd, Winsted, CT 06098
    660 E Wakefield Blvd, Winsted, CT 06098
    660 E Wakefield Blvd, Winsted, CT 06098
    /28

    $749,999

    Pending
    • 2 Beds
    • 2 Baths
    • 1,320 Sq Ft

    660 E Wakefield Blvd, Winsted, CT 06098

    Nestled along the coveted east side of Highland Lake, 660 East Wakefield Blvd offers a rare opportunity to create the waterfront retreat you've always imagined. Bursting with classic lake charm and timeless character, this home is ready for a new owner to make it their own and bring fresh vision to an unforgettable setting. Enjoy excellent water access for swimming, boating, kayaking, and

    Patrick Smith Smith & DeGroat Real Estate

    660 E Wakefield Blvd, 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 $182,963

    Last Listing Agent Ryan Horvay Smith & DeGroat Real Estate

    111 Torringford St Unit 33, Winsted, CT 06098
  • 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
  • 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 $254,930

    Last Listing Agent Jill Menard Realty One Group Cutting Edge

    115 Laurel Way, Winsted, CT 06098
  • 624 Wynne Rd, Winsted, CT 06098
    624 Wynne Rd, Winsted, CT 06098
    624 Wynne Rd, Winsted, CT 06098
    /24

    $174,900

    $25K PRICE DROP
    • Land
    • 5,227 Sq Ft
    • $1,457,500 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
  • 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
    • 45 Beach St, Winsted, CT 06098

      Est $222,383

      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

  • 426 Platt Hill Rd, Winsted, CT 06098
    426 Platt Hill Rd, Winsted, CT 06098
    426 Platt Hill Rd, Winsted, CT 06098
    /39

    $679,900

    • 3 Beds
    • 2.5 Baths
    • 2,806 Sq Ft

    426 Platt Hill Rd, Winsted, CT 06098

    Custom built log Home!This home sits on a 3 acre, private landscaped lot with mountains laurel and a park nearby. This sprawling home with a covered front porch(28x 8)is perfect for relaxing and features over 1100 sq of decking which wraps around the house for entertaining. The Home features a stunning living room with interior balcony, chandeliers, field stone wood fireplace, cathedral ceiling,

    Mary Mary LeBlanc Realty

    426 Platt Hill Rd, Winsted, 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 $194,633

    Last Listing Agent Bethany Lydem Stone Crest Realty LLC

    111 Riverton Rd Unit 61, Winsted, CT 06098
  • 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

Showing Results 81 - 120, Page 3 of 18

Connecticut Litchfield County Winsted

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