4,844

Winsted, CT Homes

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

    $199,900

    • Land
    • 5,227 Sq Ft
    • $1,665,833 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
  • 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 $249,521

    Last Listing Agent Rob Rosa Berkshire Hathaway NE Prop.

    94 Holabird Ave, Winsted, CT 06098
    • 234 Oak St, Winsted, CT 06098

      Est $259,500

      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

      • 10% Above List Price
      • $180/SF
      • 29 Days On Market
      • Last Sold Price $235,000
      • Dec 27, 2023

      Last Listing Agent Timothy McGrane Berkshire Hathaway Home Services

  • 258 Perch Rock Trail, Winsted, CT 06098
    258 Perch Rock Trail, Winsted, CT 06098
    258 Perch Rock Trail, Winsted, CT 06098
    /39

    $795,000

    Pending
    • 4 Beds
    • 2 Baths
    • 1,373 Sq Ft

    258 Perch Rock Trail, Winsted, CT 06098

    Turn-key direct waterfront gem on Highland Lake! Perfectly positioned on the desirable east side of the lake, this beautifully maintained Cape offers abundant sunshine, gorgeous sunsets, & stunning water views. The updated kitchen features a breakfast bar, generous cabinet space, & opens to the dining room & inviting great room with hardwood floors & a gas fireplace. Enjoy lake views from the

    Nancy Reardon Berkshire Hathaway NE Prop.

    258 Perch Rock Trail, Winsted, CT 06098
  • 389 Colebrook River Rd, Winsted, CT 06098

    $319,900

    Sold Aug 29, 2025

    389 Colebrook River Rd, Winsted, CT 06098

    • 2 Beds
    • 1.5 Baths
    • 1,034 Sq Ft
    • Built 1950

    Last Sold Summary

    • $309/SF
    • 57 Days On Market

    Last Listing Agent David Sartirana Northwest CT Realty

    389 Colebrook River Rd, Winsted, CT 06098
    • 24 Union St, Winsted, CT 06098

      Est $291,372

      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

      • 17% Above List Price
      • $97/SF
      • 47 Days On Market
      • Last Sold Price $250,000
      • Apr 25, 2024

      Last Listing Agent Farzaneh RE/MAX

  • 350 Walnut St, Winsted, CT 06098
    350 Walnut St, Winsted, CT 06098
    350 Walnut St, Winsted, CT 06098
    /25

    $285,000

    $5K PRICE INCREASE Pending
    • 2 Beds
    • 1 Bath
    • 720 Sq Ft

    350 Walnut St, Winsted, CT 06098

    Fully remodeled from top to bottom, 350 Walnut St offers the perfect blend of modern updates, efficient living, and outdoor space. This move-in-ready 2-bedroom, 1-bath ranch has been beautifully reimagined with a fresh, stylish feel and all the major improvements already done for you. Inside, you will find a brand-new kitchen with quartz countertops and stainless-steel appliances, a fully updated

    Vincent Miller Hudson Home Services LLC

    350 Walnut St, 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 $383,550

    Last Listing Agent Mary Mary LeBlanc Realty

    41 Lovely St, 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
      • Dec 07, 2023

      Last Listing Agent Kirk Coates Luxe Estates, Inc

  • 149 E Mountain Ave, Winsted, CT 06098
    149 E Mountain Ave, Winsted, CT 06098
    149 E Mountain Ave, Winsted, CT 06098
    /38

    $274,900

    Pending
    • 2 Beds
    • 1 Bath
    • 993 Sq Ft

    149 E Mountain Ave, Winsted, CT 06098

    Welcome to this beautifully updated single-level home offering the ease of one-floor living. This charming property features two spacious bedrooms and an updated full bathroom, along with a generously sized living room perfect for relaxing or entertaining. The renovated kitchen boasts modern finishes and stainless steel appliances, providing both style and functionality. A heated sunroom adds

    Kevin Eagan Berkshire Hathaway NE Prop.

    149 E Mountain Ave, 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 $374,467

    Last Listing Agent Lana Van Valkenburgh Vision Real Estate

    166 Torringford St, Winsted, CT 06098
    • 42 Upland Rd, Winsted, CT 06098

      Est $249,975

      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

      • 20% Above List Price
      • $169/SF
      • 71 Days On Market
      • Last Sold Price $209,000
      • Jul 11, 2024

      Last Listing Agent Glenn Kohrs Coldwell Banker Realty

  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /26

    $239,000

    Under Contract
    • 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
  • 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
    • 125 E Mountain Ave, Winsted, CT 06098

      Est $311,320

      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
      • Mar 18, 2024

      Last Listing Agent David Sartirana Northwest CT Realty

  • 118 South Rd, Winsted, CT 06098
    118 South Rd, Winsted, CT 06098
    118 South Rd, Winsted, CT 06098
    /36

    $419,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 2,240 Sq Ft

    118 South Rd, Winsted, CT 06098

    Tucked away in a peaceful country setting just minutes from Winchester Center, this well-maintained 4-bedroom Colonial offers space, comfort, and timeless charm. Proudly owned by just one owner, this home reflects true pride of ownership throughout, with thoughtfully updated mechanicals and the added peace of mind of a whole-house generator. The inviting main level features a spacious family room

    Becky Grieco Berkshire Hathaway NE Prop.

    118 South Rd, Winsted, CT 06098
  • 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 $361,760

    Last Listing Agent Christine Hunter Hunter Real Estate, LLC

    409 N Main St, Winsted, CT 06098
    • 103 E Mountain Ave, Winsted, CT 06098

      Est $257,413

      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

      • 6% Below List Price
      • $211/SF
      • 29 Days On Market
      • Last Sold Price $275,000
      • Aug 01, 2024

      Last Listing Agent David Merrigan Merrigan & Lefebvre Realty

  • 217 Walnut St, Winsted, CT 06098
    217 Walnut St, Winsted, CT 06098
    217 Walnut St, Winsted, CT 06098
    /34

    $399,000

    Under Contract
    • 5 Beds
    • 4 Baths
    • 2,779 Sq Ft

    217 Walnut St, Winsted, CT 06098

    In-Town Victorian 2-Family - Exceptional Condition & Versatility Rare opportunity to own a beautifully maintained, vinyl-sided Victorian-style side-by-side two-family home in a prime in-town location! This unique property offers incredible flexibility for investors, owner-occupants, or multi-generational living. Each unit features its own private entrance and spacious layout-one side offering a

    David D'Amore Northwest CT Realty

    217 Walnut St, Winsted, CT 06098
  • 15 John St, Winsted, CT 06098

    $288,557

    Sold Oct 29, 2025

    15 John St, Winsted, CT 06098

    • 3 Beds
    • 2 Baths
    • 1,538 Sq Ft
    • Built 1900

    Last Sold Summary

    • 3% Below List Price
    • $188/SF
    • 38 Days On Market

    Current Estimated Value $279,905

    Last Listing Agent Amanda Balaski Northwest CT Realty

    15 John St, Winsted, CT 06098
    • 129 Forest Ave, Winsted, CT 06098

      Est $596,419

      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

      • 11% Below List Price
      • $279/SF
      • 195 Days On Market
      • Last Sold Price $670,000
      • Nov 22, 2024

      Last Listing Agent Daniel Burgio William Raveis Real Estate

  • 57 Main St, Winsted, CT 06098
    57 Main St, Winsted, CT 06098
    57 Main St, Winsted, CT 06098
    /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
  • 30 Rock St, Winsted, CT 06098

    $235,000

    Sold Nov 24, 2025

    30 Rock St, Winsted, CT 06098

    • 4 Beds
    • 2 Baths
    • 2,299 Sq Ft
    • Built 1874

    Last Sold Summary

    • 4% Above List Price
    • $102/SF
    • 8 Days On Market

    Current Estimated Value $236,943

    Last Listing Agent Patrick Precourt Meridian Realty Group LLC

    30 Rock St, Winsted, CT 06098
    • 143 Mountain Rd, Winsted, CT 06098

      Est $318,098

      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

      • 14% Above List Price
      • $223/SF
      • 92 Days On Market
      • Last Sold Price $279,000
      • Jan 16, 2024

      Last Listing Agent Don Sciarretto Berkshire Hathaway Home Services

  • 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
  • 155 Mathew Rd, Winsted, CT 06098

    $314,000

    Sold May 30, 2025

    155 Mathew Rd, Winsted, CT 06098

    • 2 Beds
    • 1.5 Baths
    • 1,536 Sq Ft
    • Built 1979

    Last Sold Summary

    • 3% Below List Price
    • $204/SF
    • 56 Days On Market

    Current Estimated Value $311,106

    Last Listing Agent Austin Brochu Sullivan Real Estate Inc

    155 Mathew Rd, Winsted, CT 06098
    • 11 Orchard St, Winsted, CT 06098

      Est $211,656

      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

      • 29% Above List Price
      • $93/SF
      • 19 Days On Market
      • Last Sold Price $164,000
      • Apr 29, 2024

      Last Listing Agent Jonathan Gineo Silver and Oak Realty

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

    $299,900

    • 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
  • 112 Shore Dr, Winsted, CT 06098

    $862,500

    Sold Jul 23, 2025

    112 Shore Dr, Winsted, CT 06098

    • 3 Beds
    • 3 Baths
    • 2,113 Sq Ft
    • Built 1955

    Last Sold Summary

    • 11% Below List Price
    • $408/SF
    • 61 Days On Market

    Current Estimated Value $869,159

    Last Listing Agent Nancy Reardon Berkshire Hathaway NE Prop.

    112 Shore Dr, Winsted, CT 06098
    • 303 E Wakefield Blvd, Winsted, CT 06098

      Est $274,885

      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

      • $286/SF
      • 21 Days On Market
      • Last Sold Price $275,000
      • Nov 06, 2024

      Last Listing Agent Tammy Schaller William Raveis Real Estate

  • 184 Smith Hill Rd, Winsted, CT 06098
    184 Smith Hill Rd, Winsted, CT 06098
    184 Smith Hill Rd, Winsted, CT 06098
    /37

    $765,000

    • 3 Beds
    • 2.5 Baths
    • 4,387 Sq Ft

    184 Smith Hill Rd, Winsted, CT 06098

    Beautiful Private Brick/Clapboard Tudor set back on 8.46 private acres (which includes an extra 2+ acre abutting lot). New Hand Split Cedar Shingled Roof and new rebuilt brick chimney set off this custom elegant home. All warm cherry wood floors and special custom moldings throughout the home add charm. Classy center island Kit with new subzero, granite counters & bow window-Fireplaced Dining

    Mary New Berkshire Hathaway NE Prop.

    184 Smith Hill Rd, Winsted, CT 06098
  • 128 Danbury Quarter Rd, Winsted, CT 06098

    $320,000

    Sold Sep 30, 2025

    128 Danbury Quarter Rd, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1965

    Last Sold Summary

    • 8% Above List Price
    • $333/SF
    • 34 Days On Market

    Current Estimated Value $320,797

    Last Listing Agent Kim Trumbull William Raveis Real Estate

    128 Danbury Quarter Rd, Winsted, CT 06098
    • 151 Hinsdale Ave, Winsted, CT 06098

      Est $262,765

      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

      • 19% Above List Price
      • $135/SF
      • 154 Days On Market
      • Last Sold Price $220,000
      • Sep 11, 2023

      Last Listing Agent Sarah Isabella Glenstone Real Estate LLC

  • 431 W Wakefield Blvd, Winsted, CT 06098
    431 W Wakefield Blvd, Winsted, CT 06098
    431 W Wakefield Blvd, Winsted, CT 06098
    /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
  • 14 Pratt St, Winsted, CT 06098

    $167,900

    Sold Nov 14, 2025

    14 Pratt St, Winsted, CT 06098

    • 3 Beds
    • 1.5 Baths
    • 1,340 Sq Ft
    • Built 1900

    Last Sold Summary

    • 16% Below List Price
    • $125/SF
    • 24 Days On Market

    Last Listing Agent Amy Sartirana Northwest CT Realty

    14 Pratt St, Winsted, CT 06098
    • 111 Riverton Rd Unit 83, Winsted, CT 06098

      Est $197,401

      Not Listed For Sale

      111 Riverton Rd Unit 83, Winsted, CT 06098

      • 2 Beds
      • 1.5 Baths
      • 1,204 Sq Ft
      • Built 1987
      111 Riverton Rd Unit 83, Winsted, CT 06098

      Last Sold Summary

      • 1% Below List Price
      • $166/SF
      • 65 Days On Market
      • Last Sold Price $200,000
      • Dec 13, 2024

      Last Listing Agent David Sartirana Northwest CT Realty

  • 150 Oak St, Winsted, CT 06098
    150 Oak St, Winsted, CT 06098
    150 Oak St, Winsted, CT 06098
    /19

    $579,000

    • 11 Beds
    • 5.5 Baths
    • 5,233 Sq Ft

    150 Oak St, Winsted, CT 06098

    150 Oak St. is a fully rented, rare, charming 1920's 5-family apartment home located in a beautiful residential neighborhood in Winsted/Winchester, CT. Old World charm with original woodwork, high ceilings, mostly hardwood floors, and hallways connecting the spacious rooms in 4 of the units -which feature 2 bedrooms and a dining room. The 5th floor is a 3 bedroom, 1 1/2 bath unit with electric

    Pamela Silvestri Turning Point Realty, LLC

    150 Oak St, Winsted, CT 06098
  • 10 Meeting House Rd, Winsted, CT 06063

    $255,000

    Sold Jun 24, 2025

    10 Meeting House Rd, Winsted, CT 06063

    • 3 Beds
    • 2 Baths
    • 1,524 Sq Ft
    • Built 1970

    Last Sold Summary

    • 31% Above List Price
    • $167/SF
    • 5 Days On Market

    Current Estimated Value $439,523

    Last Listing Agent Scott Holmes William Pitt Sotheby's Int'l

    10 Meeting House Rd, Winsted, CT 06063
    • 16 Alexandria Dr, Winsted, CT 06063

      Est $523,636

      Not Listed For Sale

      16 Alexandria Dr, Winsted, CT 06063

      • 4 Beds
      • 2.5 Baths
      • 2,364 Sq Ft
      • Built 1989
      16 Alexandria Dr, Winsted, CT 06063

      Last Sold Summary

      • 25% Above List Price
      • $177/SF
      • 17 Days On Market
      • Last Sold Price $418,000
      • Sep 01, 2023

      Last Listing Agent Gina Beiser Executive Real Estate

  • 63 Meadow St, Winsted, CT 06098
    63 Meadow St, Winsted, CT 06098
    63 Meadow St, Winsted, CT 06098
    /35

    $345,000

    • 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

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Connecticut Litchfield County Winsted

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