Winchester, CT Homes

• 

  $375,000 Sold Feb 19, 2025

  220 Gilbert Ave, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 2,176 Sq Ft
  • Built 1900

  Last Sold Summary

  • 6% Below List Price
  • $172/SF
  • 77 Days On Market

  Current Estimated Value $362,017

  Last Listing Agent Linda Muraski Century 21 Classic Homes

  220 Gilbert Ave, Winsted, CT 06098
• 

  Est $202,034 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 734 Sq Ft

  110 E Mountain Ave, Winsted, CT 06098

  110 E Mountain Ave, Winsted, CT 06098
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  /15

  $175,000 Under Contract

  • 2 Beds
  • 1.5 Baths
  • 992 Sq Ft

  45 Riveredge Dr Unit 45, Winsted, CT 06098

  If you know the complex, you know it is a nicely secluded, pleasant place to live. The unit offers a nice private rear patio area. It is a lovely location by the Still River, yet close to town and offers easy access the region via highway and train from NYC to Waterbury. l Two-hour drive to NYC or Boston if traffic is kind. 45 minutes to Tanglewood, 40 to Hartford. The interior does not need a

  John Herman The Buyer's Representative LLC

  45 Riveredge Dr Unit 45, Winsted, CT 06098
• 

  $500,000 Sold Jan 31, 2025

  368 Sandy Brook Rd, Colebrook, CT 06021

  • 3 Beds
  • 1.5 Baths
  • 2,532 Sq Ft
  • Built 1830

  Last Sold Summary

  • 4% Below List Price
  • $197/SF
  • 11 Days On Market

  Current Estimated Value $525,232

  Last Listing Agent Nick Palazzo Century 21 Clemens Group

  368 Sandy Brook Rd, Colebrook, CT 06021
• 

  Est $299,697 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,582 Sq Ft

  24 Union St, Winsted, CT 06098

  24 Union St, Winsted, CT 06098
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  /27

  $375,000

  • 3 Beds
  • 3,660 Sq Ft

  57 Main St, Winsted, CT 06098

  Wonderful multiuse property on Main St. in Winsted. Currently used as a cleaners on the first floor and residential unit on the second floor. Multiple possibilities for this building which is in a prime location. Potential to take over the current business and rent or live in second floor, covert to multifamily or start a new business venture. This property is also listed as commercial with MLS

  Stacy LaQuerre Regall Realty, LLC

  57 Main St, Winsted, CT 06098
• 

  $862,500 Sold Jul 23, 2025

  112 Shore Dr, Winsted, CT 06098

  • 3 Beds
  • 3 Baths
  • 2,113 Sq Ft
  • Built 1955

  Last Sold Summary

  • 11% Below List Price
  • $408/SF
  • 61 Days On Market

  Current Estimated Value $874,836

  Last Listing Agent Nancy Reardon Berkshire Hathaway NE Prop.

  112 Shore Dr, Winsted, CT 06098
• 

  Est $235,284 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 1,334 Sq Ft

  174 Wallens St Unit C7, Winsted, CT 06098

  174 Wallens St Unit C7, Winsted, CT 06098
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  /16

  $279,999

  • 3 Beds
  • 2 Baths
  • 1,652 Sq Ft

  118 Meadow St, Winsted, CT 06098

  This charming historic home, built in 1860, blends timeless character with thoughtful updates. Featuring 3-4 bedrooms, this property offers flexible living space to meet your needs. The beautifully remodeled upstairs bathroom is a standout feature, offering modern comfort within this classic home. Enjoy your LARGE eat-in kitchen with laundry hook ups and plenty of natural lighting and ample

  Ashley Henry The Washington Agency

  118 Meadow St, Winsted, CT 06098
• 

  $410,000 Sold Apr 24, 2025

  52 Lakeview Rd, Winsted, CT 06098

  • 4 Beds
  • 3.5 Baths
  • 2,313 Sq Ft
  • Built 1971

  Last Sold Summary

  • 5% Below List Price
  • $177/SF
  • 28 Days On Market

  Current Estimated Value $428,779

  Last Listing Agent David Sartirana Northwest CT Realty

  52 Lakeview Rd, Winsted, CT 06098
• 

  Est $242,617 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,236 Sq Ft

  42 Upland Rd, Winsted, CT 06098

  42 Upland Rd, Winsted, CT 06098
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  /37

  $500,000 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 3,416 Sq Ft

  440 Platt Hill Rd, Winsted, CT 06098

  Distinctive Country Estate with Two Homes on 9.6 Rolling Acres Set amid 9.6 picturesque country acres, this unique property offers two homes and endless potential. The stone and stucco main residence features eight spacious rooms, including four bedrooms and four fireplaces, blending classic character with old-world charm. Rolling open land and mature trees surround the home, providing an ideal

  David D'Amore Northwest CT Realty

  440 Platt Hill Rd, Winsted, CT 06098
• 

  $320,000 Sold Sep 30, 2025

  128 Danbury Quarter Rd, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1965

  Last Sold Summary

  • 8% Above List Price
  • $333/SF
  • 34 Days On Market

  Last Listing Agent Kim Trumbull William Raveis Real Estate

  128 Danbury Quarter Rd, Winsted, CT 06098
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  Est $322,925 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,622 Sq Ft

  125 E Mountain Ave, Winsted, CT 06098

  125 E Mountain Ave, Winsted, CT 06098
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  $850,000

  • Land
  • 116.5 Acres
  • $7,296 per Acre

  82 Riverton Rd, Colebrook, CT 06021

  Escape to Your Own 116 acres of Paradise in Colebrook, CT! Discover 116 +/- acres of picturesque land nestled along Riverton Road in the heart of scenic Colebrook, Connecticut. This extraordinary property offers a rare opportunity to own a vast expanse of rural beauty, complete with two serene ponds, winding old logging roads, and a mix of standing hardwoods and softwoods that create a lush,

  Suzie Larson Turning Point Realty, LLC

  82 Riverton Rd, Colebrook, CT 06021
• 

  $167,900 Sold Nov 14, 2025

  14 Pratt St, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,340 Sq Ft
  • Built 1900

  Last Sold Summary

  • 16% Below List Price
  • $125/SF
  • 24 Days On Market

  Last Listing Agent Amy Sartirana Northwest CT Realty

  14 Pratt St, Winsted, CT 06098
• 

  Est $206,557 Not Listed For Sale

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

  111 Riverton Rd Unit 35, Winsted, CT 06098

  111 Riverton Rd Unit 35, Winsted, CT 06098
• 

  $320,000 Sold May 16, 2025

  47 Moore Ave, Winsted, CT 06098

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

  Last Sold Summary

  • 8% Above List Price
  • $212/SF
  • 29 Days On Market

  Current Estimated Value $326,150

  Last Listing Agent Suzie Larson Turning Point Realty, LLC

  47 Moore Ave, Winsted, CT 06098
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  Est $282,193 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,304 Sq Ft

  103 E Mountain Ave, Winsted, CT 06098

  103 E Mountain Ave, Winsted, CT 06098
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  $146,000 Sold Feb 10, 2025

  35 Riveredge Dr Unit 35, Winsted, CT 06098

  • 2 Beds
  • 1.5 Baths
  • 992 Sq Ft
  • Built 1986

  Last Sold Summary

  • 6% Below List Price
  • $147/SF
  • 3 Days On Market

  Current Estimated Value $157,333

  Last Listing Agent Maria Smith KW Legacy Partners

  35 Riveredge Dr Unit 35, Winsted, CT 06098
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  Est $672,900 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  129 Forest Ave, Winsted, CT 06098

  129 Forest Ave, Winsted, CT 06098
• 

  $439,900 Sold Dec 04, 2025

  819 E Wakefield Blvd, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,892 Sq Ft
  • Built 1920

  Last Sold Summary

  • 12% Below List Price
  • $233/SF
  • 72 Days On Market

  Last Listing Agent David Sartirana Northwest CT Realty

  819 E Wakefield Blvd, Winsted, CT 06098
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  Est $383,409 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,249 Sq Ft

  143 Mountain Rd, Winsted, CT 06098

  143 Mountain Rd, Winsted, CT 06098
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  $155,000 Sold Jan 09, 2025

  20 Riveredge Dr Unit 20, Winsted, CT 06098

  • 2 Beds
  • 1.5 Baths
  • 992 Sq Ft
  • Built 1986

  Last Sold Summary

  • $156/SF
  • 1 Day On Market

  Current Estimated Value $164,418

  Last Listing Agent Maria Smith KW Legacy Partners

  20 Riveredge Dr Unit 20, Winsted, CT 06098
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  Est $243,118 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,759 Sq Ft

  11 Orchard St, Winsted, CT 06098

  11 Orchard St, Winsted, CT 06098
• 

  $190,000 Sold Oct 20, 2025

  111 Torringford St Unit 25, Winsted, CT 06098

  • 2 Beds
  • 2 Baths
  • 1,156 Sq Ft
  • Built 1987

  Last Sold Summary

  • 6% Above List Price
  • $164/SF
  • 2 Days On Market

  Last Listing Agent Ron Rudek Connecticut Realty, LLC

  111 Torringford St Unit 25, Winsted, CT 06098
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  Est $296,330 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  303 E Wakefield Blvd, Winsted, CT 06098

  303 E Wakefield Blvd, Winsted, CT 06098
• 

  $240,000 Sold Oct 22, 2025

  210 Walnut St, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,056 Sq Ft
  • Built 1988

  Last Sold Summary

  • 7% Above List Price
  • $227/SF
  • 46 Days On Market

  Last Listing Agent Nicole Araujo Trend 2000 Real Estate

  210 Walnut St, Winsted, CT 06098
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  Est $265,056 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,634 Sq Ft

  151 Hinsdale Ave, Winsted, CT 06098

  151 Hinsdale Ave, Winsted, CT 06098
• 

  $950,000 Sold Jun 27, 2025

  355 W Lake St, Winsted, CT 06098

  • 5 Beds
  • 3.5 Baths
  • 3,216 Sq Ft
  • Built 2008

  Last Sold Summary

  • 3% Below List Price
  • $295/SF
  • 55 Days On Market

  Current Estimated Value $859,201

  Last Listing Agent David Sartirana Northwest CT Realty

  355 W Lake St, Winsted, CT 06098
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  Est $213,656 Not Listed For Sale

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

  111 Riverton Rd Unit 83, Winsted, CT 06098

  111 Riverton Rd Unit 83, Winsted, CT 06098
• 

  $860,000 Sold Jun 24, 2025

  399 Colebrook Rd, Colebrook, CT 06021

  • 4 Beds
  • 3 Baths
  • 3,016 Sq Ft
  • Built 1956

  Last Sold Summary

  • 7% Below List Price
  • $285/SF
  • 90 Days On Market

  Current Estimated Value $899,915

  Last Listing Agent David Taylor Elyse Harney Real Estate

  399 Colebrook Rd, Colebrook, CT 06021
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  Est $540,263 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,364 Sq Ft

  16 Alexandria Dr, Winsted, CT 06063

  16 Alexandria Dr, Winsted, CT 06063
• 

  $1,500,000 Sold Oct 14, 2025

  538 Wheelers Point, Winsted, CT 06098

  • 4 Beds
  • 3 Baths
  • 2,496 Sq Ft
  • Built 1930

  Last Sold Summary

  • 20% Below List Price
  • $601/SF
  • 292 Days On Market

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

  538 Wheelers Point, Winsted, CT 06098
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  Est $351,221 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,664 Sq Ft

  5 Hillside Ave, Winsted, CT 06098

  5 Hillside Ave, Winsted, CT 06098
• 

  $225,000 Sold Nov 03, 2025

  130 Stanton Ave, Winsted, CT 06098

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1979

  Last Sold Summary

  • 4% Below List Price
  • $293/SF
  • 115 Days On Market

  Last Listing Agent David D'Amore Northwest CT Realty

  130 Stanton Ave, Winsted, CT 06098
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  Est $248,502 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,380 Sq Ft

  36 S Main St, Winsted, CT 06098

  36 S Main St, Winsted, CT 06098
• 

  $292,000 Sold Jul 25, 2025

  126 Williams Ave, Winsted, CT 06098

  • 6 Beds
  • 2 Baths
  • 2,225 Sq Ft
  • Built 1890

  Last Sold Summary

  • 2% Above List Price
  • $131/SF
  • 42 Days On Market

  Current Estimated Value $282,594

  Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

  126 Williams Ave, Winsted, CT 06098
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  Est $212,673 Not Listed For Sale

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

  111 Riverton Rd Unit 55, Winsted, CT 06098

  111 Riverton Rd Unit 55, Winsted, CT 06098
• 

  $90,000 Sold Apr 25, 2025

  109 Marshall St, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 936 Sq Ft
  • Built 1935

  Last Sold Summary

  • 1% Above List Price
  • $96/SF
  • 18 Days On Market

  Current Estimated Value $109,109

  Last Listing Agent David Sartirana Northwest CT Realty

  109 Marshall St, Winsted, CT 06098

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