Winsted, CT Homes

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  $249,900

  • 3 Beds
  • 1 Bath
  • 1,422 Sq Ft

  94 Holabird Ave, Winsted, CT 06098

  Welcome to this charming New England Colonial that blends classic character with comfortable living. Step inside to an inviting, oversized living room featuring beautiful new vinyl flooring-perfect for relaxing, entertaining guests, or gathering with family. The main living level offers two convenient bedrooms and a laundry area, making everyday living easy and practical. Upstairs, you'll find

  

  Rob Rosa

  Berkshire Hathaway NE Prop.

  (860) 492-6499

  94 Holabird Ave, Winsted, CT 06098
• Explore Winsted

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  $2,400 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,860 Sq Ft
  • House for Rent

  101 Norfolk Rd, Winsted, CT 06098

  Raised Ranch rental close to town on 1.33 wooded acres. The lower level features two large rooms with new vinyl plank flooring, fresh paint, and a spacious storage/utility room with laundry. The main floor includes a living room and an updated kitchen with quartz countertops and stainless steel appliances. Sliders lead to a large deck overlooking the private wooded yard. There is a large primary

  

  Amanda Balaski

  Northwest CT Realty

  (860) 845-0664

  101 Norfolk Rd, Winsted, CT 06098
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  $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 $367,196

  Last Listing Agent SHARON GILSON Northwest CT Realty

  147 Smith Hill Rd, Winsted, CT 06098
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  Est $264,762 Not Listed For Sale

  14 Hamill Dr, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,888 Sq Ft
  • Built 1973

  14 Hamill Dr, Winsted, CT 06098

  Last Sold Summary

  • 2% Above List Price
  • $138/SF
  • 27 Days On Market

  Last Sold Price $260,000

  Last Listing Agent Eva Casoria eXp Realty
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  $399,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 2,196 Sq Ft

  35 Glendale Ave, Winsted, CT 06098

  Welcome to this spacious and well-maintained 2,196 sq. ft. one-owner home offering comfortable living in a convenient in-town location. This 3-bedroom, 2-bath residence features an open floor plan on the main living level, highlighted by a large formal living room with fireplace, dining room, expansive family room, and an updated kitchen-perfect for both everyday living and entertaining.

  

  David Sartirana

  Northwest CT Realty

  (860) 864-5659

  35 Glendale Ave, Winsted, CT 06098
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  $165 total monthly price

  • 200 Sq Ft
  • House for Rent

  113 Elm St Unit Left, Winsted, CT 06098

  One of two available storage units. Each unit is 200 square feet and can be used as extra storage or as a garage.

  

  Jeffrey Liskin

  Northwest CT Realty

  (860) 735-3947

  113 Elm St Unit Left, Winsted, CT 06098
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  $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 $927,583

  Last Listing Agent Keith Meyer Northwest CT Realty

  43 E Lake St, Winsted, CT 06098
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  Est $207,823 Not Listed For Sale

  111 Riverton Rd Unit 17, Winsted, CT 06098

  • 2 Beds
  • 1.5 Baths
  • 1,204 Sq Ft
  • Built 1987

  111 Riverton Rd Unit 17, Winsted, CT 06098

  Last Sold Summary

  • 4% Above List Price
  • $166/SF
  • 87 Days On Market

  Last Sold Price $199,900

  Last Listing Agent Joanne Donne The Washington Agency
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  /25

  $279,900 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft

  44 Lewis St, Winsted, CT 06098

  Enjoy years of maintenance-free living in this beautifully maintained 3-bedroom, 2-bath home, ideally situated on a quiet side street just minutes from the beach at Highland Lake and the shops, restaurants, and conveniences of downtown Winsted. Completely remodeled in 2017, this home offers a long list of updates at that time including a new roof, updated baths, remodeled kitchen, all new

  

  David Sartirana

  Northwest CT Realty

  (860) 318-9799

  44 Lewis St, Winsted, CT 06098
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  $165 total monthly price

  • 200 Sq Ft
  • House for Rent

  113 Elm St Unit Right, Winsted, CT 06098

  One of two available storage units. Each unit is 200 square feet and can be used as extra storage or as a garage.

  

  Jeffrey Liskin

  Northwest CT Realty

  (860) 809-5763

  113 Elm St Unit Right, Winsted, CT 06098
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  $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 $473,102

  Last Listing Agent Mark Porriello RE/MAX Right Choice

  288 Torringford St, Winsted, CT 06098
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  Est $276,037 Not Listed For Sale

  86 Maple St, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 1,428 Sq Ft
  • Built 1880

  86 Maple St, Winsted, CT 06098

  Last Sold Summary

  • 3% Above List Price
  • $188/SF
  • 128 Days On Market

  Last Sold Price $268,000

  Last Listing Agent Chris LaCava Coldwell Banker Realty
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  $24,900

  • Land
  • 0.44 Acre
  • $56,591 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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  $1,695 total monthly price

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

  131-133 Willow St, Winchester, 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) 981-0563

  131-133 Willow St, Winchester, CT 06098
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  $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 $311,269

  Last Listing Agent David Sartirana Northwest CT Realty

  49 Walnut St, Winsted, CT 06098
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  Est $54,402 Not Listed For Sale

  287 Colebrook Rd, Winsted, CT 06098

  287 Colebrook Rd, Winsted, CT 06098

  Last Sold Summary

  • 9% Above List Price
  • $1/SF
  • 180 Days On Market

  Last Sold Price $50,000

  Last Listing Agent Adam Towers Berkshire Hathaway Home Services
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  $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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  $1,500 total monthly price

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

  244 Walnut St, Winsted, CT 06098

  Bright first-floor 2-bedroom, 1-bath apartment available at 244 Walnut St in Winsted, CT. This well-maintained unit features all new windows that provide plenty of natural light and improved energy efficiency, along with natural gas heat for affordable utilities. Conveniently located in a quiet residential area close to downtown Winsted, shopping, and local amenities. Comfortable first-floor

  

  William Kallberg

  Berkshire Hathaway NE Prop.

  (860) 730-1457

  244 Walnut St, Winsted, CT 06098
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  $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 $343,810

  Last Listing Agent Meagan Albert Tier 1 Real Estate

  171 Wallens St, Winchester, CT 06098
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  Est $46,759 Not Listed For Sale

  90 Reaching Hill Rd, Winsted, CT 06098

  90 Reaching Hill Rd, Winsted, CT 06098

  Last Sold Summary

  • 23% Above List Price
  • 184 Days On Market

  Last Sold Price $38,000

  Last Listing Agent Christopher Gueniat Northwest CT Realty
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  $469,000

  • 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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  $1,495 total monthly price

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

  112 Rockwell St Unit 1, Winsted, CT 06098

  Bright and sunny, first floor, 2 bedroom apartment. Washer/dryer in the unit. Large, private porch. Pets considered. Off street parking. Minimum credit score required. Credit and background check done by listing office. required. Two months security, if applicable.

  

  Amanda Balaski

  Northwest CT Realty

  (860) 609-3853

  112 Rockwell St Unit 1, Winsted, CT 06098
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  $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

  Current Estimated Value $283,131

  Last Listing Agent Michael J Flaherty Jr Sullivan Real Estate Inc

  39 Orchard St, Winsted, CT 06098
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  Est $120,303 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

  • 29% Above List Price
  • $163/SF
  • 62 Days On Market

  Last Sold Price $93,000

  Last Listing Agent Amanda Cole Carol Cole Real Estate, LLC
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  $23,900 Pending

  • 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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  /10

  $1,450 total monthly price

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

  79 Chestnut St, Winsted, CT 06098

  Located at 79 Chestnut Street, this third-floor apartment offers 2 bedrooms and 1 full bathroom with approximately 750 sq ft of living space in a multi-family building built in 1915. The unit features a comfortable layout with a living room, kitchen, and two bedrooms, along with thermopane windows and natural gas baseboard heating. A washer/dryer hookup is conveniently located inside the unit,

  

  William Kallberg

  Berkshire Hathaway NE Prop.

  (860) 981-0377

  79 Chestnut St, Winsted, CT 06098
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  $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 $230,049

  Last Listing Agent David Sartirana Northwest CT Realty

  32 Charles St, Winsted, CT 06098
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  Est $119,748 Not Listed For Sale

  11 Gibbs St Unit 4, Winsted, CT 06098

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

  11 Gibbs St Unit 4, Winsted, CT 06098

  Last Sold Summary

  • 50% Above List Price
  • $140/SF
  • 8 Days On Market

  Last Sold Price $80,000

  Last Listing Agent Susan Belmonte Coldwell Banker Realty
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  $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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  /7

  $1,195 total monthly price

  • 1 Bed
  • 1 Bath
  • 1,400 Sq Ft
  • House for Rent

  112 Rockwell St Unit LL, Winsted, CT 06098

  Private 1bedroom apartment with its own porch and yard, plus in-unit washer/dryer. Pets considered. Conveniently located near the center of town and Highland Lake. First month's rent plus two months' security deposit required. Credit and background check performed by the listing office.

  

  Amanda Balaski

  Northwest CT Realty

  (860) 321-4592

  112 Rockwell St Unit LL, Winsted, CT 06098
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  $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 $285,713

  Last Listing Agent Margaret Alexson Elyse Harney Real Estate

  174 Boyd St, Winsted, CT 06098
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  Est $286,580 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

  • 6% Above List Price
  • $182/SF
  • 59 Days On Market

  Last Sold Price $270,000

  Last Listing Agent Beth Cantor Coldwell Banker
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  $339,900 Coming Soon

  • 2 Beds
  • 1 Bath
  • 975 Sq Ft

  621 Wynne Rd, Winsted, CT 06098

  Tucked away on a private road in the sought-after Highland Lake district, this impeccably maintained Ranch offers the perfect blend of privacy, simplicity, and natural beauty. Built in 1995 and set on a .59-acre lot, the home is surrounded by over 500 acres of preserved land, creating a peaceful, nature-filled setting that is increasingly hard to find. Inside, the home features 975 square feet of

  

  David Sartirana

  Northwest CT Realty

  (860) 385-6622

  621 Wynne Rd, 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
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  $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 $296,089

  Last Listing Agent Alison Malkin Essentia Realty

  331 Colebrook Rd, Winsted, CT 06098
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  Est $345,368 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

  • 5% Above List Price
  • $359/SF
  • 19 Days On Market

  Last Sold Price $330,000

  Last Listing Agent Kathryn Ekstrom Haynes Real Estate Services
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  $370,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,715 Sq Ft

  351 Platt Hill Rd, Winsted, CT 06098

  Summer is coming-be ready for it at 351 Platt Hill Road! Tucked away in a scenic setting yet only 1 mile from Highland Lake, this 3-bedroom, 2-bath home is the perfect year-round retreat or weekend getaway. Leave the stairs behind and enjoy true one-level living. The floor plan is designed for easy flow, featuring a primary suite and two additional bedrooms on the main floor. The surprise factor

  Valerie Nash KW Legacy Partners

  351 Platt Hill Rd, Winsted, CT 06098
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  $800 total monthly price

  • 1 Bath
  • 4,668 Sq Ft
  • House for Rent

  440 Main St Unit C, Winchester, CT 06098

  Two room Studio apartment set in town. Convenient to stores, restaurants and medical facility.

  Linda Ganem Borla & Associates Real Estate

  440 Main St Unit C, Winchester, CT 06098
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  $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 $164,532

  Last Listing Agent Erin Ruwet Century 21 AllPoints Realty

  37 Riveredge Dr Unit 37, Winsted, CT 06098
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  Est $285,790 Not Listed For Sale

  139 Boyd St, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 2,104 Sq Ft
  • Built 1885

  139 Boyd St, Winsted, CT 06098

  Last Sold Summary

  • 22% Above List Price
  • $112/SF
  • 29 Days On Market

  Last Sold Price $235,000

  Last Listing Agent Mary Mary LeBlanc Realty

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