Winsted, CT Homes

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  /39

  $399,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,969 Sq Ft

  208 Spencer Hill Rd, Winsted, CT 06098

  Discover this beautifully maintained 3-bedroom, 1.5-bath Colonial set on a level one-acre lot less than two miles from town. This home has been thoughtfully updated over the years and is truly move-in ready. Enjoy a spacious living room and family room, each featuring a cozy fireplace-perfect for New England seasons. The updated kitchen offers modern appliances and a bright, comfortable

  

  David Sartirana

  Northwest CT Realty

  (860) 431-6356

  208 Spencer Hill Rd, Winsted, CT 06098
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  Explore Winsted

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  /18

  $1,600 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,890 Sq Ft
  • Townhouse for Rent

  31 Benton St, Winchester, CT 06098

  Adorable Duplex, newly remodeled Kitchen and bath. Harwood floors throughout with a new gas furnace. Deck off kitchen. A must see!

  

  Victoria Stillings

  Coldwell Banker Realty

  (860) 743-1027

  31 Benton St, Winchester, CT 06098
• 

  $362,000 Sold Nov 18, 2025

  147 Smith Hill Rd, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 1,910 Sq Ft
  • Built 1949

  Last Sold Summary

  • 6% Below List Price
  • $190/SF
  • 84 Days On Market

  Last Listing Agent SHARON GILSON Northwest CT Realty

  147 Smith Hill Rd, Winsted, CT 06098
• 

  Not Listed For Sale

  • 8 Beds
  • 5 Baths
  • 5,093 Sq Ft

  247 N Main St, Winsted, CT 06098

  247 N Main St, Winsted, CT 06098
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  /31

  $339,000

  • 6 Beds
  • 2.5 Baths
  • 2,376 Sq Ft

  157 Elm St, Winsted, CT 06098

  Bring your vision to this spacious 6-bedroom, 2.5-bath home full of character and potential. Featuring a newer roof and boiler, this property offers peace of mind while leaving room for your personal touch. Enjoy the classic Victorian details and generous layout, perfect for creating your dream home. Situated on a sidewalk-lined street just steps from downtown eateries, a local brewery, and

  

  Doreen Gagnon

  Coldwell Banker Realty

  (860) 590-8606

  157 Elm St, Winsted, CT 06098
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  /34

  $1,500 - $1,800 per month plus fees

  Mill at Still River

  1 - 2 Beds

  101 Whiting St, Winsted, CT 06098

  By far the best place to live in Winsted, Connecticut. Turn of the century construction, every unit overlooks the beautiful Still River, our 700-1000 square-foot one and two bedroom interiors are bright and charming and feature exposed wood beams, 10-foot ceilings, oversized industrial windows, and exposed brick walls. We deliver nature at your door. Our community amenities include same-floor

  101 Whiting St, Winsted, CT 06098
• 

  $920,000 Sold Nov 17, 2025

  43 E Lake St, Winsted, CT 06098

  • 4 Beds
  • 3 Baths
  • 2,131 Sq Ft
  • Built 2002

  Last Sold Summary

  • 3% Below List Price
  • $432/SF
  • 56 Days On Market

  Last Listing Agent Keith Meyer Northwest CT Realty

  43 E Lake St, Winsted, CT 06098
• 

  Not Listed For Sale

  • 8 Beds
  • 8 Baths
  • 3,963 Sq Ft

  155 Gilbert Ave, Winchester Center, CT 06098

  155 Gilbert Ave, Winchester Center, CT 06098
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  /34

  $299,900 Pending

  • 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

  (860) 374-7309

  49 Walnut St, Winsted, CT 06098
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  /17

  $1,800 total monthly price

  • 3 Beds
  • 1.5 Baths
  • 1,557 Sq Ft
  • Townhouse for Rent

  830 Main St, Winsted, CT 06098

  Fabulous opportunity for the growing family to rent a 3 bedroom duplex with a 1st floor office or study. Completely renovated. Large Walk-up attic is finished as a primary bedroom. This large 1/2 house has 1.5 baths, formal living room and formal dining. 1/2 bath has a stackable washer and dryer in the unit. Pets allowed (40lbs max) with approval. One month security. Credit and background checks

  Christine Hunter Hunter Real Estate, LLC

  830 Main St, Winsted, CT 06098
• 

  $460,000 Sold Jun 20, 2025

  288 Torringford St, Winsted, CT 06098

  • 4 Beds
  • 3 Baths
  • 3,021 Sq Ft
  • Built 1875

  Last Sold Summary

  • 14% Below List Price
  • $152/SF
  • 128 Days On Market

  Current Estimated Value $481,172

  Last Listing Agent Mark Porriello RE/MAX Right Choice

  288 Torringford St, Winsted, CT 06098
• 

  Est $361,923 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,606 Sq Ft

  283 Colebrook Rd, Winsted, CT 06098

  283 Colebrook Rd, Winsted, CT 06098
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  /2

  $23,900

  • Land
  • 0.15 Acre
  • $159,333 per Acre

  48 Bridge St, Winsted, CT 06098

  Nestled just steps from downtown, this .15-acre lot offers a fantastic opportunity in a highly convenient location. The property is fairly level and provides easy access to shopping, restaurants, The Gilson Theater, and Little Red Barn Brewery. With city water and sewer available, this lot is ready for your vision. Whether you're looking to build or invest, this prime spot puts you right in the

  

  David Sartirana

  Northwest CT Realty

  (860) 453-5624

  48 Bridge St, Winsted, CT 06098
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  /23

  $1,150 - $1,550 per month plus fees

  Gilbert Clock Apartments

  Studio - 2 Beds

  13 Wallens St, Winsted, CT 06098

  At Gilbert Clock Apartments , our designer-inspired amenities set us apart from the competition. We pride ourselves on providing top-quality apartments outfitted with the everyday amenities you expect as well as luxury amenities to delight your senses and enhance your modern life. Indulge your culinary instincts in your state-of-the-art kitchen, furnished with Beautiful and energy-efficient

  13 Wallens St, Winsted, CT 06098
• 

  $208,900 Sold Jul 18, 2025

  39 Orchard St, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Built 1875

  Last Sold Summary

  • 9% Below List Price
  • $174/SF
  • 131 Days On Market

  Last Listing Agent Michael J Flaherty Jr Sullivan Real Estate Inc

  39 Orchard St, Winsted, CT 06098
• 

  Est $55,108 Not Listed For Sale

  287 Colebrook Rd, Winsted, CT 06098

  287 Colebrook Rd, Winsted, CT 06098
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  /8

  $299,900 Pending

  • 6 Beds
  • 2 Baths
  • 2,699 Sq Ft

  77 Hubbard St, Winsted, CT 06098

  Discover this versatile two-family residence offering a blend of modern updates and timeless charm. Each unit boasts three bedrooms and a full bath, providing ample space and comfort for tenants or multi-generational living. The first-floor unit has been beautifully renovated, featuring a brand-new kitchen with stylish finishes, updated bath, gleaming hardwood floors, and plush new carpet in the

  

  Amy Rio

  Executive Real Estate Inc.

  (860) 452-3957

  77 Hubbard St, Winsted, CT 06098
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  /32

  $1,700 total monthly price

  • 2 Beds
  • 1 Bath
  • 3,303 Sq Ft
  • House for Rent

  135 Elm St Unit 1, Winsted, CT 06098

  Extra large, first floor, 2 bedroom apartment with beautiful hardwood floors and finishes. Huge, eat-in kitchen with all appliances and washer and dryer for added convenience. Located in a beautiful neighborhood nearby schools, medical facilities, restaurants, shopping and outdoor recreation. Route 8 is also close by for easy commute.

  Susanne Vasquez Coldwell Banker Realty

  135 Elm St Unit 1, Winsted, CT 06098
• 

  $225,000 Sold Dec 10, 2025

  32 Charles St, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,044 Sq Ft
  • Built 1953

  Last Sold Summary

  • 2% Below List Price
  • $216/SF
  • 41 Days On Market

  Last Listing Agent David Sartirana Northwest CT Realty

  32 Charles St, Winsted, CT 06098
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  Est $46,959 Not Listed For Sale

  90 Reaching Hill Rd, Winsted, CT 06098

  90 Reaching Hill Rd, Winsted, CT 06098
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  /22

  $179,900 Pending

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

  111 Riverton Rd Unit 90, Winsted, CT 06098

  Discover the ease of condo living with the charm of a riverside retreat at Riverwalk Condos. This beautifully cared-for 2-bedroom, 1.5-bath home offers an inviting layout designed for comfort and relaxation. The spacious living room with its warm fireplace opens to a private deck overlooking the Still River-an ideal spot to unwind at the end of the day or entertain with a view. The kitchen also

  

  David Sartirana

  Northwest CT Realty

  (860) 615-2545

  111 Riverton Rd Unit 90, Winsted, CT 06098
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  /12

  $1,495 per month plus fees

  Litchfield Heights

  2 Beds

  15 Mountain View Terrace, Winsted, CT 06098

  Litchfield Heights Apartments is nestled quietly in the greenery of the Berkshires. We are situated close to the border of Massachusetts with easy access from Routes 8 & 44. We offer generously sized 1 bedroom flats, and 2 or 3 bedroom Townhouse. Enjoy the ease of maintenance free living when you make Litchfield Heights Apartments your home. Call Litchfield Heights Apartments today for further

  15 Mountain View Terrace, Winsted, CT 06098
• 

  $280,000 Sold Jun 16, 2025

  174 Boyd St, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,424 Sq Ft
  • Built 1900

  Last Sold Summary

  • 8% Below List Price
  • $197/SF
  • 110 Days On Market

  Current Estimated Value $280,686

  Last Listing Agent Margaret Alexson Elyse Harney Real Estate

  174 Boyd St, Winsted, CT 06098
• 

  Est $117,714 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft

  11 Gibbs St Unit 6, Winsted, CT 06098

  11 Gibbs St Unit 6, Winsted, CT 06098
• 

  /2

  $29,000

  • Land
  • 0.44 Acre
  • $65,909 per Acre

  124 Rockwell St, Winsted, CT 06098

  124 Rockwell St. - Versatile .44-Acre Lot Near Downtown This .44-acre lot offers a prime location close to downtown with city water and sewer available in the street. The previous home sat at street level, while the majority of the lot slopes below, creating a unique landscape with plenty of potential. With a little imagination and the right site contractor, this property presents endless

  

  David Sartirana

  Northwest CT Realty

  (860) 891-6121

  124 Rockwell St, Winsted, CT 06098
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  /10

  $1,500 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,199 Sq Ft
  • House for Rent

  22 Upson Ave, Winsted, CT 06098

  Beautiful First-Floor Apartment with Classic Charm and Modern Updates! This spacious first-floor apartment features gleaming hardwood floors, fresh paint, and an updated kitchen. Enjoy the high ceilings and beautiful woodwork that add character and warmth throughout. Conveniently located close to downtown, offering easy access to shopping, dining, and commuting routes.

  Kelly Sullivan Sullivan Real Estate Inc

  22 Upson Ave, Winsted, CT 06098
• 

  $300,000 Sold Nov 07, 2025

  331 Colebrook Rd, Winsted, CT 06098

  • 2 Beds
  • 1.5 Baths
  • 1,323 Sq Ft
  • Built 1940

  Last Sold Summary

  • 7% Above List Price
  • $227/SF
  • 25 Days On Market

  Last Listing Agent Alison Malkin Essentia Realty

  331 Colebrook Rd, Winsted, CT 06098
• 

  Est $122,370 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
• 

  /2

  $29,000

  • Land
  • 1.88 Acres
  • $15,426 per Acre

  52 White St, Winsted, CT 06098

  Discover the possibilities with this 1.8-acre parcel located on a peaceful in-town street. The property offers a convenient location close to town amenities while maintaining a quiet, private setting. Public water and sewer are available in the street, though not currently connected to the property. While the land is developable, the seller will retain easements for drainage and access to

  

  David Sartirana

  Northwest CT Realty

  (860) 856-5386

  52 White St, Winsted, CT 06098
• 

  /2

  $1,050 per month plus fees

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Condo for Rent

  12 Beach St Unit 7, Winsted, CT 06098

  Property Id: 1615805Total 8 - 1 BED ROOM UNITS in the building CLOSE to Route 8 & WINSTED Mainstreet, on-site parking, coin operated laundry, REAR BALCONY.

  12 Beach St Unit 7, Winsted, CT 06098
• 

  $160,000 Sold May 07, 2025

  37 Riveredge Dr Unit 37, Winsted, CT 06098

  • 2 Beds
  • 1.5 Baths
  • 992 Sq Ft
  • Built 1986

  Last Sold Summary

  • $161/SF
  • 37 Days On Market

  Current Estimated Value $163,423

  Last Listing Agent Erin Ruwet Century 21 AllPoints Realty

  37 Riveredge Dr Unit 37, Winsted, CT 06098
• 

  Est $292,097 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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  /36

  $499,000

  • 3 Beds
  • 2 Baths
  • 2,167 Sq Ft

  197 Spencer Hill Rd, Winsted, CT 06098

  Discover the charm of this spacious contemporary Cape, set on a peaceful one-acre lot in a desirable rural neighborhood. Offering over 3,000 square feet of living space, this well-maintained home provides a flexible layout ideal for today's lifestyle. The main level features a formal living room, dining room, updated kitchen, den, sunroom with fireplace and hot tub, full bath, and convenient

  

  David Sartirana

  Northwest CT Realty

  (860) 419-0914

  197 Spencer Hill Rd, Winsted, CT 06098
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  /37

  $4,000 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft
  • House for Rent

  880 W Wakefield Blvd, Winsted, CT 06098

  Discover lakeside living at its finest with this fully renovated, fully furnished 3 bedroom, sleeps 10, 2 full-baths, family estate set on a half acre of professionally landscaped grounds overlooking picturesque Highland Lake. Located just 0.6 miles from Main Street Winsted and Red Barn Brewing, this property combines serene lakefront living with convenient access to local amenities. Enjoy use of

  Matt Crossen Coldwell Banker Realty

  880 W Wakefield Blvd, Winsted, CT 06098
• 

  $495,000 Sold Jun 09, 2025

  704 W Wakefield Blvd, Winsted, CT 06098

  • 2 Beds
  • 2 Baths
  • 754 Sq Ft
  • Built 1911

  Last Sold Summary

  • 6% Above List Price
  • $656/SF
  • 4 Days On Market

  Current Estimated Value $435,435

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

  704 W Wakefield Blvd, Winsted, CT 06098
• 

  Est $353,683 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 920 Sq Ft

  103 Shore Dr, Winsted, CT 06098

  103 Shore Dr, Winsted, CT 06098
• 

  

  /22

  $245,000 Pending

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

  174 Wallens St Unit B6, Winsted, CT 06098

  Discover effortless, low-maintenance living in this inviting home located in the highly sought-after Clockmaker's Hill 55+ community. The thoughtfully designed open floor plan features 2 bedrooms and 2 full bathrooms, offering seamless flow from the spacious living room-anchored by a cozy gas fireplace-to the dedicated dining area, ideal for hosting friends and family. The sun-filled kitchen

  

  David Sartirana

  Northwest CT Realty

  (860) 507-3542

  174 Wallens St Unit B6, Winsted, CT 06098
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  /29

  $4,000 total monthly price

  • 4 Beds
  • 3.5 Baths
  • 2,265 Sq Ft
  • House for Rent

  121 W Wakefield Blvd, Winsted, CT 06098

  Discover lakeside living at its finest with this renovated 5-bedroom, 4-bath family estate set privately on a full acre overlooking picturesque Highland Lake. Located just 0.7 miles from Main Street Winsted and Red Barn Brewing, this property combines serene lakefront living with convenient access to local amenities. Enjoy use of a private dock and waterfront deck located directly across the

  Elizabeth Stockwell Coldwell Banker Realty

  121 W Wakefield Blvd, Winsted, CT 06098
• 

  $800,000 Sold Aug 04, 2025

  266 Perch Rock Trail, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • Built 1928

  Last Sold Summary

  • 7% Above List Price
  • $538/SF
  • 0 Days On Market

  Current Estimated Value $812,513

  Last Listing Agent Laurie Murray KW Legacy Partners

  266 Perch Rock Trail, Winsted, CT 06098
• 

  Est $305,542 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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