Winchester, CT Homes

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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
• Explore Winchester

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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
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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 $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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  $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
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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
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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 $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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  $49,000

  Pending

  • Land
  • 2 Acres
  • $24,500 per Acre

  18 Pine Rd, Colebrook, CT 06021

  Discover the perfect setting for your dream home on this private 2.0-acre parcel in the scenic hills of Colebrook. Featuring 236 feet of road frontage on quiet Pine Road, this property offers a beautiful building site situated on a gently elevated plateau with desirable southern and western exposures, providing excellent sunlight and the potential for stunning sunset views. Surrounded by nature

  

  David Sartirana

  Northwest CT Realty

  18 Pine Rd, Colebrook, CT 06021
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  $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
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  $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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  $305,000

  $35K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,442 Sq Ft

  103 Cordano Rd, Winsted, CT 06098

  Well-maintained Cape in a desirable rural setting, yet just minutes from shopping, dining, schools, and other everyday conveniences. This 7-room home offers 3 bedrooms and 1.5 baths with a flexible floor plan designed for comfortable living. The main level features a formal living room, dining room, kitchen, family room, primary bedroom, and a full bath w/laundry, providing the convenience of

  

  David Sartirana

  Northwest CT Realty

  103 Cordano Rd, 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
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  $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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  $799,900

  • 2 Beds
  • 1 Bath
  • 1,044 Sq Ft

  804 W Wakefield Blvd, Winsted, CT 06098

  Experience an everyday vacation at 804 W. Wakefield Blvd on beautiful Highland Lake! This exceptional turnkey, year-round waterfront retreat is ideal as a primary residence, weekend escape, vacation home, or income-producing rental. Perfectly positioned on the widest part of Highland Lake's coveted Third Bay, enjoy breathtaking sunrises, panoramic water views, and bald eagles soaring overhead

  

  Pamela Dostilio

  Coldwell Banker Realty

  804 W Wakefield Blvd, Winsted, CT 06098
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  $1,800 Plus Fees

  • 3 Beds
  • 1 Bath
  • 1,260 Sq Ft
  • House for Rent

  335 Taylor Brook Rd, Winchester, CT 06098

  Welcome to your new home in Winsted, Winchester, CT! This charming property offers an inviting atmosphere perfect for comfortable living. Its convenient location places you near several great restaurants, making dining out a breeze. Plus, the Community Health & Wellness Center is just a short 14-minute drive away, ensuring easy access to health services.This property features essential

  335 Taylor Brook Rd, 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 $298,097

  Last Listing Agent David Sartirana Northwest CT Realty

  49 Walnut St, Winsted, CT 06098
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  Est $613,372

  Not Listed For Sale

  97 Taylor Rd, Barkhamsted, CT 06063

  • 4 Beds
  • 3 Baths
  • 3,100 Sq Ft
  • Built 1990

  97 Taylor Rd, Barkhamsted, CT 06063

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Heidi Picard-Ramsay Berkshire Hathaway NE Prop.
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  $429,000

  $121K 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

  55 Walnut St, Winsted, CT 06098
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  /20

  $2,800 Plus Fees

  • 3 Beds
  • 1.5 Baths
  • 1,510 Sq Ft
  • Condo for Rent

  506 Main St, New Hartford, CT 06057

  Open house Monday, August 17th 4-6 pm Historic charm meets modern convenience in this updated 3-bedroom, 1.5 bath duplex located in the heart of New Hartford, CT. Built circa 1900, this spacious 1,510 sq. ft. home offers preserved character with thoughtful updates throughout.Available for immediate occupancy, the home features a spacious kitchen with new roof, dishwasher,

  506 Main St, New Hartford, CT 06057
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  $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 $706,667

  Not Listed For Sale

  711 W Wakefield Blvd, Winchester Center, CT 06098

  • 3 Beds
  • Built 1800

  711 W Wakefield Blvd, Winchester Center, CT 06098

  Last Sold Summary

  • 371 Days On Market

  Last Listing Agent Peter Kores The Washington Agency
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  $45,000

  • Land
  • 17,859 Sq Ft
  • $109,756 per Acre

  32 Hubbard St, Winsted, CT 06098

  Rare opportunity to build in a convenient in-town location! This level 0.41-acre lot is ideally situated close to downtown amenities while offering easy access to Highland Lake's public beach and boat launch. Formerly improved with a three-story Colonial home, the property presents a unique opportunity to redevelop an established homesite. Public water, public sewer, and natural gas are available

  

  David Sartirana

  Northwest CT Realty

  32 Hubbard St, Winsted, 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
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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 $365,710

  Last Listing Agent Meagan Albert Tier 1 Real Estate

  171 Wallens St, Winchester, 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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  $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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  $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
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  $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 $750,391

  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

  • 22 Days On Market

  Last Listing Agent Lori Meyerson Coldwell Banker Realty
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  /2

  $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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  $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
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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 $251,884

  Last Listing Agent David Sartirana Northwest CT Realty

  32 Charles St, Winsted, CT 06098
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  Est $394,343

  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

  • 39 Days On Market

  Last Listing Agent Tracy Macgowan Elyse Harney Real Estate
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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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  /12

  $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
• 

  $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
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  Est $792,708

  Not Listed For Sale

  139 Bunnell St, Colebrook, CT 06021

  • 5 Beds
  • 3.5 Baths
  • 3,427 Sq Ft
  • Built 1792

  139 Bunnell St, Colebrook, CT 06021

  Last Sold Summary

  • 66 Days On Market

  Last Listing Agent Mitzi Muller William Raveis Real Estate

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