Winsted, CT Homes

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  $1,600,000

  Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,129 Sq Ft

  752 Lake Dr, Winsted, CT 06098

  Experience the best of lakefront living with breathtaking views, spectacular sunsets, and exceptional outdoor spaces. This amazing waterfront home features a brand-new 100' x 14' Brazilian hardwood deck, a 35' x 6' stationary Trex and steel dock, and a private cabana-perfect for relaxing, boating, swimming, and entertaining. Soak in panoramic water views from multiple vantage points, including

  

  Pam Famiglietti

  William Raveis Real Estate

  752 Lake Dr, Winsted, CT 06098
• Explore Winsted

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  /17

  $1,400 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,100 Sq Ft
  • House for Rent

  104 Elm St, Winsted, CT 06098

  Spacious two-bedroom, 1.5-bath apartment conveniently located close to downtown. The kitchen features a convenient pantry for additional storage and offers direct access to a covered rear porch-perfect for enjoying your morning coffee or relaxing outdoors. The apartment also offers plenty of storage, including dedicated basement storage space and a walk-up attic with additional room for your

  

  Jeffrey Liskin

  Northwest CT Realty

  104 Elm 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

  Current Estimated Value $396,515

  Last Listing Agent SHARON GILSON Northwest CT Realty

  147 Smith Hill Rd, Winsted, CT 06098
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  Est $341,303

  Not Listed For Sale

  141 Maloney Ct, Winsted, CT 06098

  • 4 Beds
  • 2.5 Baths
  • 1,752 Sq Ft
  • Built 1963

  141 Maloney Ct, Winsted, CT 06098

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Marcy D'Angelo Coldwell Banker Realty
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  $399,900

  • 4 Beds
  • 1.5 Baths
  • 1,944 Sq Ft

  122 Standard Ave, Winsted, CT 06098

  Well-maintained 4-bedroom Colonial tucked away on a quiet dead-end street. This inviting home features a newly renovated eat-in kitchen with updated cabinetry, countertops, and finishes, perfect for everyday living and gathering. The comfortable layout includes a spacious living room and dining area, while four bedrooms offer flexibility for family, guests, or a home office. Enjoy the large yard,

  

  Amanda Balaski

  Northwest CT Realty

  122 Standard Ave, Winsted, CT 06098
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  Starting at $1,500 Plus Fees

  • 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

  Mill at Still River

  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

  Current Estimated Value $991,896

  Last Listing Agent Keith Meyer Northwest CT Realty

  43 E Lake St, Winsted, CT 06098
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  Est $874,955

  Not Listed For Sale

  266 Perch Rock Trail, Winsted, CT 06098

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

  266 Perch Rock Trail, Winsted, CT 06098

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Laurie Murray KW Legacy Partners
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  $349,900

  $20K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 2,722 Sq Ft

  70 Walnut St, Winsted, CT 06098

  Step back in time and experience the timeless elegance of this spacious 2,722 sq. ft. Victorian offering 10 rooms, 5 bedrooms, and 1.5 baths. Rich in original character and architectural detail, this classic home showcases beautiful hardwood floors, impressive natural woodwork, pocket doors, built-ins, decorative moldings, and stunning stained-glass accents that capture the craftsmanship of a

  

  David Sartirana

  Northwest CT Realty

  70 Walnut St, Winsted, CT 06098
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  /4

  $1,495 Per Month

  • 2 Beds
  • 1 Bath
  • 856 Sq Ft
  • House for Rent

  99-101 Elm St, Winsted, CT 06098

  Two bedroom, first floor apartment with laundry hook-up in the unit. Washer/dryer can be added for an additional $100 per month. Close to downtown. Off street parking, pets considered. Gas and electric heat. First month, two months security required. Background and credit check done by listing office.

  

  Amanda Balaski

  Northwest CT Realty

  99-101 Elm St, Winsted, CT 06098
• 

  $365,000

  Sold May 15, 2026

  262 Holabird Ave, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,312 Sq Ft
  • Built 1973

  Last Sold Summary

  • 1% Above List Price
  • $278/SF
  • 11 Days On Market

  Current Estimated Value $364,708

  Last Listing Agent Mary Anne Casey D. Beckley Realty

  262 Holabird Ave, Winsted, CT 06098
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  Est $467,448

  Not Listed For Sale

  50 Lakeview Rd, Winsted, CT 06098

  • 4 Beds
  • 2.5 Baths
  • 2,086 Sq Ft
  • Built 1970

  50 Lakeview Rd, Winsted, CT 06098

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Paula Nelson William Raveis Real Estate
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  $320,000

  Pending

  • 2 Beds
  • 1 Bath
  • 1,128 Sq Ft

  729 W Wakefield Blvd, Winsted, CT 06098

  Lake views that will knock your socks off! Welcome to your own slice of paradise on the shores of Highland Lake, where every day feels like a vacation. Perfectly positioned on one of Connecticut's most sought-after lakes. This home needs some love, but has great bones! Bring your vision and create your dream home!

  

  Annie Q Simard

  LPT Realty

  729 W Wakefield Blvd, Winsted, CT 06098
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  Starting at $1,150 Plus Fees

  • 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

  Gilbert Clock Apartments

  

  13 Wallens St, Winsted, CT 06098
• 

  $185,000

  Sold Jul 22, 2026

  30 Upland Rd, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 1,844 Sq Ft
  • Built 1869

  Last Sold Summary

  • 16% Below List Price
  • $100/SF
  • 48 Days On Market

  Current Estimated Value $221,703

  Last Listing Agent Jeffrey Liskin Northwest CT Realty

  30 Upland Rd, Winsted, CT 06098
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  Est $587,233

  Not Listed For Sale

  144 Marshall St, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,744 Sq Ft
  • Built 1980

  144 Marshall St, Winsted, CT 06098

  Last Sold Summary

  • 51 Days On Market

  Last Listing Agent Monica Palmerie RE/MAX RISE
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  /13

  $398,000

  Pending

  • 5 Beds
  • 3 Baths
  • 2,496 Sq Ft

  26 Elm St, Winchester, CT 06098

  Welcome to 26 Elm Street, a newly renovated and legally converted three-family property in the heart of Winsted. This is a rare opportunity for investors or owner-occupants seeking a move-in-ready, income-producing asset with strong upside potential. Two of the units have been completely renovated, featuring updated interiors that appeal to today's tenants, while the exterior has also been

  

  Annie Q Simard

  LPT Realty

  26 Elm St, Winchester, CT 06098
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  $950

  Total Monthly Price

  • 4 Beds
  • 1 Bath
  • 1,254 Sq Ft
  • House for Rent

  14 Curtice St, Winsted, CT 06098

  14 Curtice 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

  Current Estimated Value $298,097

  Last Listing Agent David Sartirana Northwest CT Realty

  49 Walnut St, Winsted, CT 06098
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  Est $148,030

  Not Listed For Sale

  287 Colebrook Rd, Winsted, CT 06098

  287 Colebrook Rd, Winsted, CT 06098

  Last Sold Summary

  • 180 Days On Market

  Last Listing Agent Adam Towers Berkshire Hathaway NE Prop.
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  /40

  $959,900

  Pending

  • 2 Beds
  • 1.5 Baths
  • 1,472 Sq Ft

  204 E Wakefield Blvd, Winsted, CT 06098

  Exceptional Highland Lake waterfront Colonial rebuilt in 1996 to modern standards and codes, offering quality construction and timeless appeal. Perfectly positioned with 58 feet of direct northwest-facing waterfront, this home is designed to capture breathtaking lake views from nearly every angle. The spacious living/great room features a dramatic fieldstone fireplace and walls of glass with

  

  David Sartirana

  Northwest CT Realty

  204 E Wakefield Blvd, Winsted, CT 06098
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  /9

  $1,500 Per Month

  • 2 Beds
  • 2 Baths
  • 950 Sq Ft
  • Property for Rent

  936 Main St Unit 14, Winchester, CT 06098

  Recently purchased and re-built manufactured home community in Winsted in final stages of being completed. The entrance to the property is being worked on now with 3 new homes to be put in front. Beautiful free standing ranch style homes, 2 bedroom, 2 baths with attached closed porch available. There are 2 houses available at this time for the same price. The other is larger with 2 bedrooms and

  Michael Block Building Blocks LLC

  936 Main St Unit 14, Winchester, CT 06098
• 

  $341,000

  Sold Jul 10, 2026

  188 Glendale Ave, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,118 Sq Ft
  • Built 1966

  Last Sold Summary

  • 5% Above List Price
  • $305/SF
  • 10 Days On Market

  Current Estimated Value $321,272

  Last Listing Agent Mary Anne Casey D. Beckley Realty

  188 Glendale Ave, Winsted, CT 06098
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  Est $112,907

  Not Listed For Sale

  11 Gibbs St Unit 9, Winsted, CT 06098

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft
  • Built 1985

  11 Gibbs St Unit 9, Winsted, CT 06098

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent David Sartirana Northwest CT Realty
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  $299,000

  Under Contract

  • 4 Beds
  • 2 Baths
  • 2,270 Sq Ft

  64 Wheeler St, Winsted, CT 06098

  Excellent opportunity for investors! This well-maintained Victorian-style two-family home offers the perfect blend of character, functionality, and income potential. Each spacious unit features 5 rooms, 2 bedrooms, and 1 full bath, with beautiful hardwood flooring throughout and separate, efficient natural gas heating systems. The upper-level apartment also includes a charming enclosed porch,

  

  David Sartirana

  Northwest CT Realty

  64 Wheeler St, Winsted, CT 06098
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  /6

  $1,495

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 1,045 Sq Ft
  • Condo for Rent

  I 9 Nanni Dr Unit L-09, Winchester, CT 06098

  Nestled in the Hills of Litchfield County, our Large Town Homes Offer:• Updated eat in kitchen with dishwasher and modern flooring. • Spacious bedrooms with new six panel doors and sliders.• Remodeled Bathroom.• Private Entrances with Slider to backyard • Over 1000 square feet of living space with heat and hot water included.Please come see why at Litchfield

  I 9 Nanni Dr Unit L-09, Winchester, CT 06098
• 

  $370,000

  Sold Mar 25, 2026

  171 Wallens St, Winchester, CT 06098

  • 2 Beds
  • 2 Baths
  • 1,274 Sq Ft
  • Built 1957

  Last Sold Summary

  • 3% Above List Price
  • $290/SF
  • 23 Days On Market

  Current Estimated Value $365,710

  Last Listing Agent Meagan Albert Tier 1 Real Estate

  171 Wallens St, Winchester, CT 06098
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  Est $123,659

  Not Listed For Sale

  11 Gibbs St Unit 7, Winsted, CT 06098

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft
  • Built 1984

  11 Gibbs St Unit 7, Winsted, CT 06098

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent David Sartirana Northwest CT Realty
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  $324,900

  • 4 Beds
  • 2 Baths
  • 3,044 Sq Ft

  50 High St, Winsted, CT 06098

  Well-maintained two-family home offering spacious apartments, separate utilities, and a convenient location within walking distance to downtown amenities. The first-floor apartment features approximately 1,620 sq. ft. with a kitchen, living room, dining room, full bath, and 2-3 bedrooms. The second-floor apartment offers approximately 1,424 sq. ft. with a similar layout including a kitchen,

  

  David Sartirana

  Northwest CT Realty

  50 High St, Winsted, CT 06098
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  $1,195 Per Month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • House for Rent

  267 Rockwell St Unit 1st fl, Winsted, CT 06098

  Ground level 1 bedroom 1 bath unit. Walking distance to Highland Lake. Laundry hookups in the unit. No Pets No Smoking, Credit, background, eviction checks, 1st month rent, 2 months security deposit.

  Diane Carroll The Washington Agency

  267 Rockwell St Unit 1st fl, Winsted, CT 06098
• 

  $691,000

  Sold May 21, 2026

  156 Shore Dr, Winsted, CT 06098

  • 5 Beds
  • 1.5 Baths
  • 1,258 Sq Ft
  • Built 1930

  Last Sold Summary

  • 12% Below List Price
  • $549/SF
  • 31 Days On Market

  Current Estimated Value $705,666

  Last Listing Agent Bryan Palladino Showcase Realty, Inc.

  156 Shore Dr, Winsted, CT 06098
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  Est $107,377

  Not Listed For Sale

  11 Gibbs St Unit 6, Winsted, CT 06098

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft
  • Built 1985

  11 Gibbs St Unit 6, Winsted, CT 06098

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent Amanda Cole Carol Cole Real Estate, LLC
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  /2

  $29,900

  Pending

  • Land
  • 5,662 Sq Ft
  • $230,000 per Acre

  17 Birdsall St, Winsted, CT 06098

  Rare opportunity to build in a convenient in-town location! This level 0.13-acre vacant lot is within walking distance of downtown shopping, dining, and services, while also offering easy access to Highland Lake's public beach, boat launch, and recreational opportunities. This property offers an excellent combination of location and potential. Public water and public sewer are available in the

  

  David Sartirana

  Northwest CT Realty

  17 Birdsall St, Winsted, CT 06098
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  /37

  $5,000 Per Month

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

  880 W Wakefield Blvd, Winsted, CT 06098

  Available Seasonal 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.

  Matt Crossen Coldwell Banker Realty

  880 W Wakefield Blvd, 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

  Current Estimated Value $251,884

  Last Listing Agent David Sartirana Northwest CT Realty

  32 Charles St, Winsted, CT 06098
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  Est $309,830

  Not Listed For Sale

  28 Maloney Ct, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,485 Sq Ft
  • Built 1940

  28 Maloney Ct, Winsted, CT 06098

  Last Sold Summary

  • 59 Days On Market

  Last Listing Agent Beth Cantor Coldwell Banker Realty
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  /2

  $29,000

  Pending

  • Land
  • 5,227 Sq Ft
  • $241,667 per Acre

  82-84 Rockwell St, Winchester, CT 06098

  Rare opportunity to build in a convenient in-town location! This level 0.12-acre vacant lot is within walking distance of downtown shopping, dining, and services, while also offering easy access to Highland Lake's public beach, boat launch, and recreational opportunities. This property offers an excellent combination of location and potential. Public water and public sewer are available in the

  

  David Sartirana

  Northwest CT Realty

  82-84 Rockwell St, Winchester, CT 06098
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  $1,500 Per Month

  • 2 Beds
  • 1.5 Baths
  • 950 Sq Ft
  • Property for Rent

  936 Main St Unit 12, Winchester, CT 06098

  Recently purchased and re-built manufactured home community in Winsted in final stages of being completed. Beautiful free standing ranch style homes, 2 bedroom with 1 bath and 2 baths available as well as an attached entrance enclosed porch. This is a small manufactured home community. Come see these homes. You can't rent a single-family house as nice as these for the price. As each house has

  Michael Block Building Blocks LLC

  936 Main St Unit 12, Winchester, 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

  Current Estimated Value $319,014

  Last Listing Agent Alison Malkin Essentia Realty

  331 Colebrook Rd, Winsted, CT 06098
• 

  Est $367,038

  Not Listed For Sale

  103 Shore Dr, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 920 Sq Ft
  • Built 1942

  103 Shore Dr, Winsted, CT 06098

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Kathryn Ekstrom Haynes Real Estate Services

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