Winchester, CT Homes

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  /33

  $275,000

  Under Contract

  • 4 Beds
  • 1.5 Baths
  • 1,416 Sq Ft

  57 Bridge St, Winsted, CT 06098

  Step into the charm of this 1880 Colonial, featuring 4 bedrooms and 1.5 baths, just a short walk to the shops, dining, and conveniences of downtown. The main level offers a spacious eat-in kitchen, inviting living room, and a versatile bonus room that could serve as a home office or, with a little creativity, an additional bedroom, along with a half bath for added convenience. Upstairs includes

  

  David Sartirana

  Northwest CT Realty

  (860) 909-8624

  57 Bridge St, Winsted, CT 06098
• Explore Winchester

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  /6

  $1,295 Per Month

  • 1 Bed
  • 1 Bath
  • 2,031 Sq Ft
  • House for Rent

  25 Lake St, Winsted, CT 06098

  Totally renovated one bedroom apartment with a new bathroom and new flooring throughout. Washer/dryer can be added for an additional $75 per month. Pets considered. Easy access to to shopping, restaurants, and college. First month and two months security and minimum credit score required.

  

  Amanda Balaski

  Northwest CT Realty

  (860) 891-6046

  25 Lake 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 $374,510

  Last Listing Agent SHARON GILSON Northwest CT Realty

  147 Smith Hill Rd, Winsted, CT 06098
• 

  Est $369,541

  Not Listed For Sale

  244 Colebrook Rd, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 1,531 Sq Ft
  • Built 1964

  244 Colebrook Rd, Winsted, CT 06098

  Last Sold Summary

  • 2% Below List Price
  • $248/SF
  • 90 Days On Market

  • Last Sold Price $379,000
  • May 09, 2025

  Last Listing Agent Carol York For Sale By Owner Connecticut
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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

  Better Homes and Gardens Real Estate Executive Real Estate

  (860) 452-3957

  77 Hubbard St, 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

  (860) 744-5205

  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 $928,176

  Last Listing Agent Keith Meyer Northwest CT Realty

  43 E Lake St, Winsted, CT 06098
• 

  Est $190,273

  Not Listed For Sale

  154 Wallens St, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • Built 1905

  154 Wallens St, Winsted, CT 06098

  Last Sold Summary

  • $103/SF
  • 20 Days On Market

  • Last Sold Price $190,000
  • May 15, 2025

  Last Listing Agent Adam Devine Dorrance Realty
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  /35

  $339,900

  • 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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  /16

  $1,400 Per Month

  • 2 Beds
  • 1 Bath
  • 3,591 Sq Ft
  • House for Rent

  165 Elm St Unit 3, Winsted, CT 06098

  Fully renovated 2 bedroom apt. New kitchen with soft close hard wood cabinetry. Airy, spacious and light filled living room with vaulted ceilings. Both bedrooms with hardwood flooring throughout... washer/dryer hookups in unit are provided. One months rent and one month security is required. Available for immediate occupancy. Off street parking space. Winsted is a dynamic town just a 12 minute

  

  Matthew Egan

  Regency Real Estate, LLC

  (860) 453-5206

  165 Elm St Unit 3, 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 $468,414

  Last Listing Agent Mark Porriello RE/MAX Right Choice

  288 Torringford St, Winsted, CT 06098
• 

  Est $320,534

  Not Listed For Sale

  47 Moore Ave, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 1,509 Sq Ft
  • Built 1964

  47 Moore Ave, Winsted, CT 06098

  Last Sold Summary

  • $212/SF
  • 29 Days On Market

  • Last Sold Price $320,000
  • May 16, 2025

  Last Listing Agent Suzie Larson Turning Point Realty, LLC
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  /15

  $499,000

  Under Contract

  • 4 Beds
  • 2.5 Baths
  • 3,556 Sq Ft

  5 Stadler Heights, Winsted, CT 06098

  Spacious and full of potential, this 10-room home offers 4 bedrooms and 2.5 baths with plenty of room for everyone. Priced below current market value, this property presents a fantastic opportunity for buyers willing to make some cosmetic updates and build instant equity. Set in a quiet country location within a private development known for its large lots and peaceful surroundings, the home

  

  David Sartirana

  Northwest CT Realty

  (860) 467-0358

  5 Stadler Heights, Winsted, CT 06098
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  /20

  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

  (959) 335-6388

  

  13 Wallens 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 $308,184

  Last Listing Agent David Sartirana Northwest CT Realty

  49 Walnut St, Winsted, CT 06098
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  Not Listed For Sale

  104 Norfolk Rd, Winsted, CT 06098

  • 2 Beds
  • 1 Bath
  • 980 Sq Ft
  • Built 1930

  104 Norfolk Rd, Winsted, CT 06098

  Last Sold Summary

  • 1,662% Above List Price
  • $8/SF
  • 44 Days On Market

  • Last Sold Price $8,000
  • May 16, 2025

  Last Listing Agent David Sartirana Northwest CT Realty
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  /25

  $349,900

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,898 Sq Ft

  102 Wallens St, Winsted, CT 06098

  This move-in-ready Colonial-style home blends classic charm with modern updates. Featuring a remodeled kitchen with a large center island, cherry cabinets, granite countertops, stainless steel appliances, and a wine fridge. The main level also offers a dining room with refinished hardwood floors, a living room, and a flexible family room. Upstairs includes three bedrooms and a full bath, with a

  

  Amanda Balaski

  Northwest CT Realty

  (860) 544-5816

  102 Wallens St, Winsted, CT 06098
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  $2,500 Per Month

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

  188 E Lake St, Winsted, CT 06098

  Welcome to our beautiful lakeside apartment, perfect for professionals seeking a home away from home for long or short term rentals. Situated on the picturesque shores of Highland Lake, this fully renovated and furnished apartment offers stunning views and serenity that will make you never want to leave. The modern design and elegant decor create a welcoming and comfortable environment for our

  

  Annie Q Simard

  LPT Realty

  (860) 356-3877

  188 E Lake St, Winsted, 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 $338,216

  Last Listing Agent Meagan Albert Tier 1 Real Estate

  171 Wallens St, Winchester, CT 06098
• 

  Est $377,299

  Not Listed For Sale

  126 Newfield Rd, Winchester, CT 06098

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1952

  126 Newfield Rd, Winchester, CT 06098

  Last Sold Summary

  • 5% Above List Price
  • $257/SF
  • 1 Day On Market

  • Last Sold Price $360,000
  • May 22, 2023

  Last Listing Agent Heidi Picard-Ramsay Berkshire Hathaway Home Services
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  /33

  $329,900

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,582 Sq Ft

  9 Colony Dr, Winsted, CT 06098

  Welcome to 9 Colony Dr, a charming 3-bedroom, 2 full bath Cape offering a versatile and comfortable layout suited for today's lifestyle. The main level features a bright living room, a convenient first-floor bedroom, a full bath, and a modern kitchen with dining area perfect for everyday living and entertaining. The upper level offers two modestly sized bedrooms along with an additional full

  

  David Sartirana

  Northwest CT Realty

  (860) 467-1887

  9 Colony Dr, Winsted, CT 06098
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  /7

  $1,095 Plus Fees

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

  92 Oakdale Ave Unit 3, Winchester, CT 06098

  Property Id: 2510661WINSTEDOne Bedroom "Garden Style" apartment. Set on 2.5 beautiful country acres. Private & secluded in quiet residential neighborhood.Living room with glass slider leading to lovely private deck and stone walls. Nature at its best.Cute Kitchen with striking tiled back-splash and tiled floor with range and refrigerator.Tiled

  (860) 782-6375

  92 Oakdale Ave Unit 3, Winchester, 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

  Current Estimated Value $285,129

  Last Listing Agent Michael J Flaherty Jr Sullivan Real Estate Inc

  39 Orchard St, Winsted, CT 06098
• 

  Est $111,049

  Not Listed For Sale

  287 Colebrook Rd, Winsted, CT 06098

  287 Colebrook Rd, Winsted, CT 06098

  Last Sold Summary

  • 122% Above List Price
  • $1/SF
  • 180 Days On Market

  • Last Sold Price $50,000
  • Oct 25, 2024

  Last Listing Agent Adam Towers Berkshire Hathaway Home Services
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  /2

  $24,900

  $4K PRICE DROP

  • Land
  • 19,166 Sq Ft
  • $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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  /5

  $1,000 Per Month

  • 2 Beds
  • 1 Bath
  • 4,668 Sq Ft
  • Apartment for Rent

  440 Main St Unit B, Winchester, CT 06098

  Second Floor two Bedroom room apartment set in town. Convenient to stores, restaurants and medical facility.

  Linda Ganem Borla & Associates Real Estate

  440 Main St Unit B, Winchester, 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 $228,746

  Last Listing Agent David Sartirana Northwest CT Realty

  32 Charles St, Winsted, CT 06098
• 

  Est $45,484

  Not Listed For Sale

  90 Reaching Hill Rd, Winsted, CT 06098

  90 Reaching Hill Rd, Winsted, CT 06098

  Last Sold Summary

  • 20% Above List Price
  • 184 Days On Market

  • Last Sold Price $38,000
  • May 31, 2023

  Last Listing Agent Christopher Gueniat Northwest CT Realty
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  /2

  $40,000

  Pending

  • Land
  • 10,890 Sq Ft
  • $160,000 per Acre

  117 Blue St, Winchester, CT 06790

  Great opportunity for water front "picnic lot" with gorgeous views on Park Pond in Winchester. Cleared upper level would be a great spot for camping. Two docks currently in place but need some work to bring them back function. Fishing, canoeing, kayaking abound in this 82 acre body of water. A place to escape and be in the quiet simplicity of nature.

  

  Annie Q Simard

  LPT Realty

  (860) 351-6176

  117 Blue St, Winchester, CT 06790
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  /13

  $1,365 Per Month

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

  20-22 Allen St Unit 2nd flr rs, Winchester, CT 06098

  Efficient Pet Friendly 1 bedroom (second floor) rental available. Clean and bright. Private rear covered porch, gas range stainless refrigerator stackable washer and dryer provided for convenience. Trash and recycling included, only one off street parking space. Hardwood floors. Close to NWCC, shopping, restaurants, Highland Lake etc. Clean bright quiet and secure building. Gas and heat and hot

  Suzie Larson Turning Point Realty, LLC

  20-22 Allen St Unit 2nd flr rs, Winchester, 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 $276,738

  Last Listing Agent Margaret Alexson Elyse Harney Real Estate

  174 Boyd St, Winsted, CT 06098
• 

  Est $753,616

  Not Listed For Sale

  404 Colebrook Rd, Colebrook, CT 06021

  • 3 Beds
  • 2.5 Baths
  • 3,860 Sq Ft
  • Built 1989

  404 Colebrook Rd, Colebrook, CT 06021

  Last Sold Summary

  • 10% Above List Price
  • $178/SF
  • 22 Days On Market

  • Last Sold Price $687,000
  • Jul 19, 2024

  Last Listing Agent Lori Meyerson Coldwell Banker Realty
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  /2

  $49,000

  • Land
  • 16,117 Sq Ft
  • $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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  /14

  $900 Per Month

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft
  • Apartment for Rent

  277 N Main St Unit 3, Winsted, CT 06098

  Second-floor apartment available in a convenient Winsted location, close to local shops, dining, and everyday amenities. This freshly painted unit offers a bright, open living space with an efficient layout, along with an in-wall A/C unit for added comfort. The kitchen provides ample cabinet storage, and the unit is complemented by a clean, well-maintained bath. Enjoy the convenience of on-site

  Ryan Marconi The Washington Agency

  277 N Main St Unit 3, 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

  Current Estimated Value $299,153

  Last Listing Agent Alison Malkin Essentia Realty

  331 Colebrook Rd, Winsted, CT 06098
• 

  Est $407,429

  Not Listed For Sale

  98 Pinney St, Colebrook, CT 06021

  • 3 Beds
  • 1 Bath
  • 1,294 Sq Ft
  • Built 1940

  98 Pinney St, Colebrook, CT 06021

  Last Sold Summary

  • 2% Above List Price
  • $309/SF
  • 39 Days On Market

  • Last Sold Price $400,000
  • Apr 21, 2025

  Last Listing Agent Tracy Macgowan Elyse Harney Real Estate
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  /37

  $449,000

  $101K PRICE DROP

  • 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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  /10

  $1,300 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
• 

  $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 $481,710

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

  704 W Wakefield Blvd, Winsted, CT 06098
• 

  Est $160,000

  Not Listed For Sale

  14 Pine Rd, Colebrook, CT 06021

  • 4 Beds
  • Built 1998

  14 Pine Rd, Colebrook, CT 06021

  Last Sold Summary

  • 16% Below List Price
  • $54/SF
  • 43 Days On Market

  • Last Sold Price $190,000
  • Dec 23, 2024

  Last Listing Agent LAURA BARTLETT Northwest CT Realty

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