Winchester, CT Homes

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  /31

  $339,000 Pending

  • 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
• Explore Winchester

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  /2

  $1,695 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,059 Sq Ft
  • House for Rent

  139 N Main St, Winsted, CT 06098

  Large 3 bedroom apartment with sun porch. Eat-in kitchen, dining room, living room and attic storage. Washer/dryer can be added for an additional $75 per month. No off street parking. Close to town, walk to NCCC. Pets considered. Credit and background check required.

  

  Amanda Balaski

  Northwest CT Realty

  (959) 207-8517

  139 N Main St, Winsted, 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
• 

  Est $391,716 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,674 Sq Ft

  19 Cottage St, Winsted, CT 06098

  19 Cottage St, Winsted, CT 06098
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  /37

  $499,999

  • 5 Beds
  • 4 Baths
  • 5,016 Sq Ft

  55 Walnut St, Winsted, CT 06098

  Timeless Victorian with Endless Possibilities.Step into a piece of history with this stunning Victorian property, a landmark in the community and home to The Maloney Funeral Home since the early 1900's. Nestled in the TCR Zone, this versatile building offers a wealth of potential. The TCR Zone allows for accessory residential uses, community centers, family day care homes, single-family

  

  David Sartirana

  Northwest CT Realty

  (860) 390-5071

  55 Walnut St, Winsted, CT 06098
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  /4

  $1,695 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Townhouse for Rent

  131 Willow St, Winsted, CT 06098

  Bright and sunny 3-bedroom duplex, ideally located close to town. This spacious home features a large eat-in kitchen, a separate dining room, and a cozy living room. Enjoy the convenience of gas heat, with washer/dryer hook-up available in the basement, or can be provided for an extra $75 per month. Minimum credit score of 700. Pets considered, and a background and credit check are required.

  

  Amanda Balaski

  Northwest CT Realty

  (860) 772-0491

  131 Willow 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
• 

  Est $345,261 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,602 Sq Ft

  63 Meadow St, Winsted, CT 06098

  63 Meadow St, 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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  /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
• 

  $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 $469,470

  Last Listing Agent Mark Porriello RE/MAX Right Choice

  288 Torringford St, Winsted, CT 06098
• 

  Est $508,497 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,532 Sq Ft

  368 Sandy Brook Rd, Colebrook, CT 06021

  368 Sandy Brook Rd, Colebrook, CT 06021
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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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  $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
• 

  $305,000 Sold Dec 22, 2025

  49 Walnut St, Winsted, CT 06098

  • 5 Beds
  • 2 Baths
  • 2,344 Sq Ft
  • Built 1824

  Last Sold Summary

  • 2% Above List Price
  • $130/SF
  • 6 Days On Market

  Last Listing Agent David Sartirana Northwest CT Realty

  49 Walnut St, Winsted, CT 06098
• 

  Est $464,097 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,933 Sq Ft

  125 Old Rd N, Winchester, CT 06098

  125 Old Rd N, Winchester, CT 06098
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  /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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  $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
• 

  $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
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  Est $376,538 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft

  126 Newfield Rd, Winchester, CT 06098

  126 Newfield Rd, Winchester, CT 06098
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  /2

  $29,000 Pending

  • 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
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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
• 

  $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
• 

  Est $378,420 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,203 Sq Ft

  191 Danbury Quarter Rd, Winchester Center, CT 06098

  191 Danbury Quarter Rd, Winchester Center, CT 06098
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  $499,000 Under Contract

  • 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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  /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
• 

  $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 $285,190

  Last Listing Agent Margaret Alexson Elyse Harney Real Estate

  174 Boyd St, Winsted, CT 06098
• 

  Est $307,806 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,267 Sq Ft

  151 Newfield Rd, Winchester, CT 06098

  151 Newfield Rd, Winchester, CT 06098
• 

  

  /30

  $315,000 Pending

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  107 Peck Rd, Winsted, CT 06098

  Turnkey 3 Bedroom, 1 bathroom home on almost an acre in Winchester. The home is sited up a long driveway in a quiet, wooded setting across from state land. Completely renovated by current owner, top to bottom. Updated kitchen & bath, new roof, new hot water heater, new Trex deck, new pellet stove, new ductless mini splits in living area and primary bedroom and much more! Attached one car garage

  

  Rebecca Doh

  W. Raveis Lifestyles Realty

  (860) 855-0150

  107 Peck Rd, Winsted, CT 06098
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  /10

  $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
• 

  $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 $62,948 Not Listed For Sale

  287 Colebrook Rd, Winsted, CT 06098

  287 Colebrook Rd, Winsted, CT 06098
• 

  /2

  $49,000

  • Land
  • 0.37 Acre
  • $132,432 per Acre

  99 Hubbard St, Winsted, CT 06098

  99 Hubbard St. - Private Lot Near Downtown & Highland Lake. Tucked away at the end of a quiet dead-end street, this .37-acre lot offers both privacy and convenience. While enjoying a peaceful setting, you're still just minutes from downtown with easy access to shopping, dining, and entertainment. Plus, Highland Lake is just a short distance away, providing endless opportunities for boating,

  

  David Sartirana

  Northwest CT Realty

  (860) 946-4468

  99 Hubbard St, 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
• 

  $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 $162,036

  Last Listing Agent Erin Ruwet Century 21 AllPoints Realty

  37 Riveredge Dr Unit 37, Winsted, CT 06098
• 

  Est $46,503 Not Listed For Sale

  90 Reaching Hill Rd, Winsted, CT 06098

  90 Reaching Hill Rd, Winsted, CT 06098
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  /26

  $229,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 1,252 Sq Ft

  18 Curtice St, Winsted, CT 06098

  Move-in ready and thoughtfully updated, this inviting home at 18 Curtice Street offers peace of mind and modern comfort. In 2005, the property was completely stripped to the studs and renovated, including updated plumbing and electrical, roof, kitchen, and baths. The heating system, along with the oil tank, was replaced in 2019. The main living level features a spacious front living room, a large

  

  David Sartirana

  Northwest CT Realty

  (860) 792-3588

  18 Curtice St, 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 $480,538

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

  704 W Wakefield Blvd, Winsted, CT 06098
• 

  Est $782,290 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,860 Sq Ft

  404 Colebrook Rd, Colebrook, CT 06021

  404 Colebrook Rd, Colebrook, CT 06021
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  $739,900 Pending

  • Land
  • 93.38 Acres
  • $7,924 per Acre

  0 Old Robertsville Rd, Winchester, CT 06098

  Nestled along a peaceful country road near the Colebrook and Barkhamsted town lines, this breathtaking 93.38-acre parcel embodies the timeless charm of rural New England. Once part of a cherished family farm, the land offers a harmonious blend of rolling meadows, majestic forests, and the gentle, winding presence of the Still River, which meanders through a substantial portion of the property.

  

  David Sartirana

  Northwest CT Realty

  (860) 650-5076

  0 Old Robertsville Rd, Winchester, CT 06098

Showing Results 1 - 40, Page 1 of 18