Winchester, CT Homes

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  $399,000 Open Fri 5:30PM - 6:30PM

  • 4 Beds
  • 1.5 Baths
  • 2,239 Sq Ft

  51 Pratt St, Winsted, CT 06098

  This stunning Renovated home is perfectly situated in the beautiful town of Winsted could be yours! Just a leisurely walk from the beautiful Highland Lake. Offering more than 2,200 square feet of thoughtfully designed living space, this home blends timeless charm with modern updates. The bright and spacious kitchen opens effortlessly into a welcoming dining area and a cozy yet expansive living

  Arlene Gonzalez The Gonzalez Property Group

  51 Pratt St, Winsted, CT 06098
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  /15

  $1,275 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,512 Sq Ft
  • House for Rent

  111 Rockwell St Unit 2, Winsted, CT 06098

  Bright and peaceful 2-bedroom, 1-bath second-floor apartment featuring a charming kitchen and a private deck. Conveniently located near downtown with off-street parking for one vehicle.

  Colin Murray Dorrance Realty

  111 Rockwell St Unit 2, Winsted, CT 06098
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  $2,200,000 Sold Oct 21, 2025

  • 4,327 Sq Ft
  • $508/SF
  • 28 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1795

  381 Smith Hill Rd, Colebrook, CT 06021

  Welcome to Stones Throw Farm. A rare and magical estate tucked on over 23 rolling, pastoral acres in the heart of Colebrook, a true New England country retreat where timeless beauty and refined simplicity come together in perfect harmony. Set along a quiet country road, this idyllic sanctuary offers an extraordinary lifestyle steeped in elegance, comfort, and the gentle rhythms of nature. At the

  Elvia Gignoux William Pitt Sotheby's Int'l

  381 Smith Hill Rd, Colebrook, CT 06021
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  Est $118,354 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft

  11 Gibbs St Unit 4, Winsted, CT 06098

  11 Gibbs St Unit 4, Winsted, CT 06098
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  $419,000

  • 3 Beds
  • 3 Baths
  • 2,747 Sq Ft

  117 South Rd, Winsted, CT 06098

  Nestled in a peaceful rural setting of Winchester Center, this charming home offers a perfect blend of rustic character and modern convenience. The property is located on over 3.3 acres of land and is adjacent to a scenic pond. Inside you will find a three bedroom two bath home with an additional in law apartment with one full bath and one bedroom and its own private entrance. The home also

  Christina Niziolek William Raveis Real Estate

  117 South Rd, Winsted, CT 06098
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  $1,175 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,512 Sq Ft
  • House for Rent

  111 Rockwell St Unit 1st Floor, Winsted, CT 06098

  Quiet & Charming 2-Bedroom - Hardwood Floors, Natural Light & Private Entrance Set on a spacious corner lot in a peaceful Winsted neighborhood, this first-floor 2-bed, 1-bath unit offers comfortable living with a functional layout and great natural light throughout. The well-appointed kitchen features ample cabinet storage, a cozy island for prep or seating, and included appliances. The living

  Colin Murray Dorrance Realty

  111 Rockwell St Unit 1st Floor, Winsted, CT 06098
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  $190,000 Sold Oct 20, 2025

  • 1,156 Sq Ft
  • $164/SF
  • 2 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1987

  111 Torringford St Unit 25, Winsted, CT 06098

  Two bedrooms, two baths plus an office - play room... New boiler and hot water heater in 2022. New carpeting. Full basement and garage. Additional photos will be added soon. Owner/Broker.

  Ron Rudek Connecticut Realty, LLC

  111 Torringford St Unit 25, Winsted, CT 06098
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  Est $395,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,872 Sq Ft

  111 Mundry Rd, Torrington, CT 06790

  111 Mundry Rd, Torrington, CT 06790
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  $439,900 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,892 Sq Ft

  819 E Wakefield Blvd, Winsted, CT 06098

  Perched directly across the street from Highland Lake's 3rd Bay, this charming 1,900 sq. ft. Cape offers sweeping lake views and the enjoyment of a permanent right-of-way to access the water. The home features 7 rooms, including 3 bedrooms and 1.5 baths, and has been thoughtfully maintained with important updates: new propane heating and hot water systems (2022), a new roof on both the house and

  David Sartirana Northwest CT Realty

  819 E Wakefield Blvd, Winsted, CT 06098
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  $2,200 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Townhouse for Rent

  188 E Lake St, Winsted, CT 06098

  Welcome to our beautiful lakeside apartment! 2 bedroom/1 Bath. Situated on the picturesque shores of Highland Lake, this fully renovated and furnished apartment offers stunning views and serenity. The apartment features a spacious living area, a fully equipped kitchen, huge primary bedroom with lake views, dedicated office space and in unit laundry. Whether you are looking for a peaceful retreat

  Annie Simard LPT Realty

  188 E Lake St, Winsted, CT 06098
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  $261,000 Sold Oct 17, 2025

  • 604 Sq Ft
  • $432/SF
  • 9 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1940

  115 Laurel Way, Winsted, CT 06098

  Welcome to 115 Laurel Way! Tucked away in a peaceful neighborhood surrounded by nature, this charming well maintained 1-bedroom, 1-bathroom home offers the perfect blend of comfort and serenity. Set on just over half an acre, the property provides ample space for outdoor living. Imagine relaxing by a cozy fire pit, enjoying warm evenings under the stars, or simply soaking in the natural beauty

  Jill Menard Realty One Group Cutting Edge

  115 Laurel Way, Winsted, CT 06098
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  Est $290,226 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,485 Sq Ft

  28 Maloney Ct, Winsted, CT 06098

  28 Maloney Ct, Winsted, CT 06098
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  $380,000 Under Contract

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

  166 Torringford St, Winsted, CT 06098

  Nothing to do but move right in to this meticulous colonial farmhouse nestled in the Litchfield Hills. This unique home combines a tasteful modern style mixed with rustic charm. Inside the fully renovated home offers a sprawling kitchen with ample counter and cabinet space, a breakfast bar with elegant quartz countertops and newer stainless steel appliances. The space is open to the dining area

  Lana Van Valkenburgh Vision Real Estate

  166 Torringford St, Winsted, CT 06098
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  $1,500,000 Sold Oct 14, 2025

  • 2,496 Sq Ft
  • $601/SF
  • 292 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1930

  538 Wheelers Point, Winsted, CT 06098

  Lakefront Historic Architecture meets Modern Styling on private waterfront penninsula with 360' direct lake frontage! Split timber tudor architecture offers unique features - leaded glass, stone flooring, window seats, paneling and mouldings, brick and stone appointments. A stunning kitchen for folks who cook, charming diningroom with bar and window seat overlooking the waterfront, and spacious

  KAREN NEWTON William Pitt Sotheby's Int'l

  538 Wheelers Point, Winsted, CT 06098
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  Est $345,730 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 920 Sq Ft

  103 Shore Dr, Winsted, CT 06098

  103 Shore Dr, Winsted, CT 06098
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  $299,900

  • 5 Beds
  • 2 Baths
  • 2,344 Sq Ft

  49 Walnut St, Winsted, CT 06098

  Well-maintained two-family home situated on a large, level lot in an area of well-cared-for properties. Conveniently located near downtown, schools, Northwestern Connecticut Community College, shopping, and restaurants. The first-floor unit features an eat-in kitchen, dining area, living room, two bedrooms, and a full bath. The second-floor unit offers a spacious kitchen/living area, 2-3

  David Sartirana Northwest CT Realty

  49 Walnut St, Winsted, CT 06098
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  $277,000 Sold Oct 09, 2025

  • 1,492 Sq Ft
  • $186/SF
  • 54 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1800

  12 Cherry St, Winsted, CT 06098

  This Home is Modern day updates Meets Old World Charm...The Updated Kitchen offers granite counter tops, custom cabinetry, tile flooring, and a pantry with Washer/ dryer hookups for convenience.. You'll find a formal dining room with hardwood floors, A main level bedroom, large living room with French doors and open stair case that leads to the upstairs.. Also on the Main level you'll find a

  Susan MCGHEE The Washington Agency

  12 Cherry St, Winsted, CT 06098
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  Est $299,728 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,104 Sq Ft

  139 Boyd St, Winsted, CT 06098

  139 Boyd St, Winsted, CT 06098
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  $229,900

  • 3 Beds
  • 1 Bath
  • 1,044 Sq Ft

  32 Charles St, Winsted, CT 06098

  Charming Cape on a Quiet Dead-End Street Welcome to 32 Charles Street - a cute and cozy 1,044 sq. ft. Cape-style home located just moments from the downtown area. The first floor offers an inviting eat-in kitchen, a comfortable living room, two bedrooms, and a full bath. Upstairs, you'll find one additional bedroom and 1 room providing flexibility for guests, a home office, or hobby space. The

  David Sartirana Northwest CT Realty

  32 Charles St, Winsted, CT 06098
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  $310,000 Sold Oct 03, 2025

  • 1,608 Sq Ft
  • $193/SF
  • 37 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1917

  36 Whiting St, Winsted, CT 06098

  Newly updated 3 bedroom 2.5 bath colonial with large front porch overlooking the Mad River. Close to downtown and town center green. This home has an updated kitchen with new quartz counters, new furnace and hot water heater along with beautifully refinished hard wood floors through out the first floor. New carpet on second floor bedrooms and the primary bedroom has its own full bathroom. The

  Brandon Riley eXp Realty

  36 Whiting St, Winsted, CT 06098
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  Est $259,507 Not Listed For Sale

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

  174 Wallens St Unit D3, Winsted, CT 06098

  174 Wallens St Unit D3, Winsted, CT 06098
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  $750,000

  • 4 Beds
  • 2 Baths
  • 5,389 Sq Ft

  436 Main St, Winsted, CT 06098

  One-of-a-Kind opportunity with 4 apartments plus a turnkey, award-winning restaurant in the heart of Litchfield County, perfectly situated in a high-traffic location. The well-established business offers 2,177 sq. ft. of warm, inviting atmosphere with 65 indoor seats and 35 outdoor seats-ideal for both casual dining and special occasions. Has a cafe license (liquor) but no bar. With a 10-year

  Tony Goia The Washington Agency

  436 Main St, Winsted, CT 06098
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  $320,000 Sold Sep 30, 2025

  • 960 Sq Ft
  • $333/SF
  • 34 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1965

  128 Danbury Quarter Rd, Winsted, CT 06098

  First-time homebuyers and downsizers take notice!. Some improvements have been done in this cozy Ranch boasting a metal roof and well-maintained mechanics. What an incredible opportunity to pick your colors and let the cosmetic upgrades take shape. A 1-car detached garage and space for a garden or outbuilding are possible on this 2.5-acre country parcel. An As-Is sale is preferred.

  Kim Trumbull William Raveis Real Estate

  128 Danbury Quarter Rd, Winsted, CT 06098
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  Est $238,522 Not Listed For Sale

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

  174 Wallens St Unit D2, Winsted, CT 06098

  174 Wallens St Unit D2, Winsted, CT 06098
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  $309,900

  • 2 Beds
  • 1 Bath
  • 702 Sq Ft

  156 Lincoln Ave, Winsted, CT 06098

  Welcome to your cozy cottage retreat in beautiful Highland Lake Community. Views of the lake from deck, public beach right around the corner. Step inside to a large mudroom, open living room, updated kitchen, 2 bedrooms, 1 full bath & laundry all on one level. New flooring and paint throughout. New roof, HW heater only 4 years old, vinyl siding, large yard with fire pit and shed. Year round lake

  Mary Mary LeBlanc Realty

  156 Lincoln Ave, Winsted, CT 06098
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  $315,000 Sold Sep 29, 2025

  • 1,747 Sq Ft
  • $180/SF
  • 85 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1900

  17 Adams St, Winsted, CT 06098

  Nestled in the charming New England town of Winsted, this classic three-bedroom, two-bathroom home at 17 Adams Street offers a blend of traditional charm and comfortable living. The property boasts a welcoming exterior with a distinguished facade, a covered front porch, and a well-maintained lawn, all framed by mature trees that provide a sense of privacy and tranquility. A convenient driveway

  Michelle Grant Coldwell Banker Premier Real Estate

  17 Adams St, Winsted, CT 06098
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  Est $240,771 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 1,334 Sq Ft

  174 Wallens St Unit D1, Winsted, CT 06098

  174 Wallens St Unit D1, Winsted, CT 06098
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  $279,999

  • 3 Beds
  • 2.5 Baths
  • 1,542 Sq Ft

  73 Norfolk Rd, Winsted, CT 06098

  New to the market! Check out this upgraded colonial home with 3 bedrooms and 2.5 baths located on a 2.6-acre wooded lot with a patio, shed and paths for walking and quadding. Enjoy entertaining in the open layout with an eat in kitchen and new cabinets. Relax in the cozy living room with hard wood floors, a fireplace and a sliding glass door to the back deck. Keep in mind the formal dining room

  Lisa Hilliard Litchfield Hills Real Estate

  73 Norfolk Rd, Winsted, CT 06098
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  $270,000 Sold Sep 25, 2025

  • 1,058 Sq Ft
  • $255/SF
  • 25 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  22 Stanton Ave, Winsted, CT 06098

  Welcome to this well-maintained 3-bedroom, 1-bathroom home located on a quiet street in the heart of Winsted. Offering 1,058 square feet of comfortable living space, this home features beautiful hardwood floors throughout and a practical layout ideal for everyday living. The kitchen includes a gas range, and the home is equipped with efficient natural gas heating and hot water, helping to keep

  Jeffrey Liskin Northwest CT Realty

  22 Stanton Ave, Winsted, CT 06098
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  Est $284,322 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,946 Sq Ft

  174 Wallens St Unit C3, Winsted, CT 06098

  174 Wallens St Unit C3, Winsted, CT 06098
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  /21

  $879,990

  • Land
  • 131.5 Acres
  • $6,692 per Acre

  000000 Norfolk Rd, Winchester, CT 06098

  Rare Multi-Parcel Land Opportunity - 5 Parcels, Endless Possibilities Discover this exceptional assemblage of five contiguous parcels spanning the scenic towns of Winchester and Colebrook in Connecticut's pristine Litchfield County. This remarkable offering combines the best of both worlds with a captivating mixture of open fields and mature forest, creating a diverse landscape that's as

  John Harney William Pitt Sotheby's Int'l

  000000 Norfolk Rd, Winchester, CT 06098
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  $330,000 Sold Sep 24, 2025

  • 1,287 Sq Ft
  • $256/SF
  • 118 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1953

  50 Manchester Heights, Winsted, CT 06098

  Charming Country Cape with Cottagecore appeal on just over an acre of land and situated on a culd-de-sac. Located off the beaten path in the quiet hills of Winchester, this storybook Cape-style home offers the perfect blend of rustic charm and modern comfort. Convenient to Route 8 and just minutes to town amenities. Enjoy the natural beauty surrounding the property while relaxing on the deck and

  Lisa Bredice Coldwell Banker Realty

  50 Manchester Heights, Winsted, CT 06098
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  Est $300,993 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,040 Sq Ft

  17 Colony Dr, Winsted, CT 06098

  17 Colony Dr, Winsted, CT 06098
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  $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

  Hector Ortiz KW Legacy Partners

  7 Stadler Heights, Winsted, CT 06098
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  $180,000 Sold Sep 23, 2025

  • 976 Sq Ft
  • $184/SF
  • 68 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1973

  1 Hamill Dr, Winsted, CT 06098

  INVESTORS, CASH BUYERS Great opportunity! Good bones! Good location! Good opportunity! Every room in this home needs your touch! Great opportunity to build sweat equity if your handy and can do some of the work yourself! The yard also needs work. Present homeowner envisioned bringing in some fill to grade the yard back behind the home. Right now it drops off and so only a little around the house

  Nancy Bard Bard Real Estate, LLC

  1 Hamill Dr, Winsted, CT 06098
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  Est $660,390 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,318 Sq Ft

  715 W Wakefield Blvd, Winsted, CT 06098

  715 W Wakefield Blvd, Winsted, CT 06098
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  $749,999

  • 5 Beds
  • 2.5 Baths
  • 2,950 Sq Ft

  151 Losaw Rd, Winsted, CT 06098

  This property is your personal sanctuary, complete with private trails for hiking your own land. Feel worlds away while being less than 2 miles to town amenities in this like-new retreat nestled on an expansive 11.59-acre lot. The eat-in-kitchen is well-equipped with ample cooking space, seamlessly connected to the formal dining room and open to living space, and leads out to the large deck with

  Breanna Goebel Compass Connecticut, LLC

  151 Losaw Rd, Winsted, CT 06098
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  $380,000 Sold Sep 17, 2025

  • 1,196 Sq Ft
  • $318/SF
  • 38 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1974

  226 E Wakefield Blvd, Winsted, CT 06098

  Welcome to your dream retreat on beautiful Highland Lake-a fully renovated gem offering the perfect blend of charm, comfort & modern updates. This lovingly maintained 3-bedroom, 1.5-bath home has been thoughtfully refreshed from top to bottom, making it truly move-in ready. Step inside to discover fresh paint throughout, newly installed floors, and beautifully updated bathrooms. The spacious

  Pascale Nejaime William Pitt Sotheby's Int'l

  226 E Wakefield Blvd, Winsted, CT 06098
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  Est $265,929 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  159 Pratt St, Winsted, CT 06098

  159 Pratt St, Winsted, CT 06098
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  $450,000

  • Land
  • 160 Acres
  • $2,812 per Acre

  430 Smith Hill Rd, Colebrook, CT 06021

  A rare opportunity to create your own private retreat in the peaceful foothills of Colebrook. Includes 18.7 acres of buildable land with the possibility to subdivide into two parcels, giving you options for your dream home or future investment. Tucked well off the beaten path, the setting is surrounded by natural beauty, offering unmatched privacy and a sense of seclusion. With selective

  Rodney Motta Berkshire Hathaway NE Prop.

  430 Smith Hill Rd, Colebrook, CT 06021

Showing Results 41 - 80, Page 2 of 18