Winchester, CT Homes

• 

  $144,000 Sold May 29, 2025

  9 Loomis St, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,768 Sq Ft
  • Built 1910

  Last Sold Summary

  • 28% Below List Price
  • $81/SF
  • 18 Days On Market

  Current Estimated Value $151,214

  Last Listing Agent Kristen Duchene Litchfield County Real Estate

  9 Loomis St, Winsted, CT 06098
• 

  Est $232,952 Not Listed For Sale

  3 Brookside Ave, Winsted, CT 06098

  • 6 Beds
  • 2,421 Sq Ft
  • Built 1900

  3 Brookside Ave, Winsted, CT 06098

  Last Sold Summary

  • 37% Above List Price
  • $70/SF
  • 78 Days On Market

  Last Sold Price $170,000

  Last Listing Agent Jayson Kemp Five Stars Realty
• 

  

  /2

  $299,900

  • Land
  • 34 Acres
  • $8,821 per Acre

  00 Ramsgate Ln, Barkhamsted, CT 06063

  30 +/- acres in ideal location in Barkhamsted bordering American Legion State Forest in the rear. Minutes from historic Riverton Center and world-renowned fly fishing. Many outdoor activities close by including hiking, biking, tubing, skiing, boating and many more. Land is ideal for almost any application, subdividing, recreation, horses, etc. Land will be subdivided upon contract and prior to

  Heidi Picard-Ramsay Berkshire Hathaway NE Prop.

  00 Ramsgate Ln, Barkhamsted, CT 06063
• 

  $293,000 Sold Oct 30, 2025

  131 Willow St, Winsted, CT 06098

  • 6 Beds
  • 2 Baths
  • 2,160 Sq Ft
  • Built 1900

  Last Sold Summary

  • 2% Below List Price
  • $136/SF
  • 83 Days On Market

  Last Listing Agent Amanda Balaski Northwest CT Realty

  131 Willow St, Winsted, CT 06098
• 

  Est $198,847 Not Listed For Sale

  111 Riverton Rd Unit 66, Winsted, CT 06098

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

  111 Riverton Rd Unit 66, Winsted, CT 06098

  Last Sold Summary

  • 11% Above List Price
  • $149/SF
  • 0 Days On Market

  Last Sold Price $179,900

  Last Listing Agent Amy Sartirana Northwest CT Realty
• 

  

  /27

  $375,000 Pending

  • 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
• 

  $315,000 Sold Sep 29, 2025

  17 Adams St, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,747 Sq Ft
  • Built 1900

  Last Sold Summary

  • 5% Above List Price
  • $180/SF
  • 85 Days On Market

  Current Estimated Value $314,065

  Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

  17 Adams St, Winsted, CT 06098
• 

  Est $251,270 Not Listed For Sale

  45 Beach St, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 2,076 Sq Ft
  • Built 1900

  45 Beach St, Winsted, CT 06098

  Last Sold Summary

  • 56% Above List Price
  • $78/SF
  • 97 Days On Market

  Last Sold Price $161,500

  Last Listing Agent Michael Barnes Coldwell Banker Realty
• 

  

  /31

  $269,999 Pending

  • 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
• 

  $85,000 Sold Mar 27, 2025

  0 Platt Hill Rd Unit 24079213, Winsted, CT 06098

  • Land
  • 3.06 Acres
  • $27,742 per Acre

  Last Sold Summary

  • 21% Above List Price
  • 5 Days On Market

  Last Listing Agent Nadia Corvo Northwest CT Realty

  0 Platt Hill Rd Unit 24079213, Winsted, CT 06098
• 

  Est $421,983 Not Listed For Sale

  193 Spencer Hill Rd, Winsted, CT 06098

  • 4 Beds
  • 2.5 Baths
  • 2,313 Sq Ft
  • Built 2012

  193 Spencer Hill Rd, Winsted, CT 06098

  Last Sold Summary

  • 46% Above List Price
  • $125/SF
  • 57 Days On Market

  Last Sold Price $290,000

  Last Listing Agent Victor Santana Santana Realty Group LLC
• 

  

  /23

  $274,900 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,267 Sq Ft

  9 Central Ave, Winsted, CT 06098

  Welcome to this adorable, solidly built Cape in the heart of Winchester, Connecticut-where home is more than just a place, it's a way of life. Nestled in the scenic Litchfield Hills, Winchester is a community full of character, rich history, and strong local businesses, offering a wonderful quality of life. From excellent schools and charming downtown shops to beautiful lakes and outdoor

  Suzie Larson Turning Point Realty, LLC

  9 Central Ave, Winsted, CT 06098
• 

  $270,000 Sold Mar 31, 2025

  325 E Wakefield Blvd, Winsted, CT 06098

  • 2 Beds
  • 1.5 Baths
  • 1,192 Sq Ft
  • Built 1930

  Last Sold Summary

  • 4% Above List Price
  • $227/SF
  • 39 Days On Market

  Current Estimated Value $286,927

  Last Listing Agent Brigitte Richter William Pitt Sotheby's Int'l

  325 E Wakefield Blvd, Winsted, CT 06098
• 

  Est $344,333 Not Listed For Sale

  160 Hinsdale Ave, Winsted, CT 06098

  • 4 Beds
  • 1.5 Baths
  • 2,379 Sq Ft
  • Built 1930

  160 Hinsdale Ave, Winsted, CT 06098

  Last Sold Summary

  • 2% Below List Price
  • $147/SF
  • 46 Days On Market

  Last Sold Price $350,000

  Last Listing Agent Laura Krzewski Realtor Bolanos & Associates LLC
• 

  

  /36

  $1,850,000

  • 9 Beds
  • 5.5 Baths
  • 7,000 Sq Ft

  431 W Wakefield Blvd, Winsted, CT 06098

  Live the Highland Lake Dream - 431 W. Wakefield Blvd, Winchester, CT Summer is just around the corner - and in Winsted, resort living never ends. Recently named one of the most desirable towns to live in, with the breathtaking Highland Lake at its heart, Winchester offers the perfect blend of beauty and lifestyle. This waterfront estate at 431 W. Wakefield Blvd isn't just a home - it's your

  Lisa Ogren Berkshire Hathaway NE Prop.

  431 W Wakefield Blvd, Winsted, CT 06098
• 

  $243,000 Sold Nov 17, 2025

  22 Curtice St, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,334 Sq Ft
  • Built 1900

  Last Sold Summary

  • $182/SF
  • 33 Days On Market

  Current Estimated Value $244,150

  Last Listing Agent Terence Dominick Exceptional Real Estate LLC

  22 Curtice St, Winsted, CT 06098
• 

  Est $251,790 Not Listed For Sale

  234 Oak St, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft
  • Built 1890

  234 Oak St, Winsted, CT 06098

  Last Sold Summary

  • 7% Above List Price
  • $180/SF
  • 29 Days On Market

  Last Sold Price $235,000

  Last Listing Agent Timothy McGrane Berkshire Hathaway Home Services
• 

  

  /9

  $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
• 

  $261,000 Sold Oct 17, 2025

  115 Laurel Way, Winsted, CT 06098

  • 1 Bed
  • 1 Bath
  • 604 Sq Ft
  • Built 1940

  Last Sold Summary

  • 4% Above List Price
  • $432/SF
  • 9 Days On Market

  Current Estimated Value $250,380

  Last Listing Agent Jill Menard Realty One Group Cutting Edge

  115 Laurel Way, Winsted, CT 06098
• 

  Est $199,633 Not Listed For Sale

  110 E Mountain Ave, Winsted, CT 06098

  • 2 Beds
  • 1 Bath
  • 734 Sq Ft
  • Built 1945

  110 E Mountain Ave, Winsted, CT 06098

  Last Sold Summary

  • 60% Above List Price
  • $170/SF
  • 36 Days On Market

  Last Sold Price $125,000

  Last Listing Agent David D'Amore Northwest CT Realty
• 

  $260,000 Sold Sep 05, 2025

  174 Wallens St Unit D3, Winsted, CT 06098

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft
  • Built 2005

  Last Sold Summary

  • 6% Above List Price
  • $192/SF
  • 1 Day On Market

  Last Listing Agent Mary New Berkshire Hathaway NE Prop.

  174 Wallens St Unit D3, Winsted, CT 06098
• 

  Est $266,094 Not Listed For Sale

  24 Union St, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 2,582 Sq Ft
  • Built 1895

  24 Union St, Winsted, CT 06098

  Last Sold Summary

  • 6% Above List Price
  • $97/SF
  • 47 Days On Market

  Last Sold Price $250,000

  Last Listing Agent Farzaneh RE/MAX
• 

  $194,900 Sold Dec 08, 2025

  111 Riverton Rd Unit 61, Winsted, CT 06098

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

  Last Sold Summary

  • 5% Below List Price
  • $162/SF
  • 61 Days On Market

  Current Estimated Value $197,374

  Last Listing Agent Bethany Lydem Stone Crest Realty LLC

  111 Riverton Rd Unit 61, Winsted, CT 06098
• 

  Not Listed For Sale

  174 Wallens St Unit C7, Winsted, CT 06098

  • 1 Bed
  • 2 Baths
  • 1,334 Sq Ft
  • Built 2005

  174 Wallens St Unit C7, Winsted, CT 06098

  Last Sold Summary

  • 7% Above List Price
  • $165/SF
  • 36 Days On Market

  Last Sold Price $220,000

  Last Listing Agent Kirk Coates Luxe Estates, Inc
• 

  $290,000 Sold Aug 28, 2025

  279 Pratt St, Winsted, CT 06098

  • 4 Beds
  • 1 Bath
  • 1,978 Sq Ft
  • Built 1880

  Last Sold Summary

  • 24% Below List Price
  • $147/SF
  • 49 Days On Market

  Current Estimated Value $305,222

  Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

  279 Pratt St, Winsted, CT 06098
• 

  Est $225,949 Not Listed For Sale

  42 Upland Rd, Winsted, CT 06098

  • 2 Beds
  • 1 Bath
  • 1,236 Sq Ft
  • Built 1891

  42 Upland Rd, Winsted, CT 06098

  Last Sold Summary

  • 8% Above List Price
  • $169/SF
  • 71 Days On Market

  Last Sold Price $209,000

  Last Listing Agent Glenn Kohrs Coldwell Banker Realty
• 

  $275,000 Sold Apr 16, 2025

  493 N Main St, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,277 Sq Ft
  • Built 1940

  Last Sold Summary

  • 6% Above List Price
  • $215/SF
  • 114 Days On Market

  Current Estimated Value $284,891

  Last Listing Agent Jessica Sperry Maverick Realty

  493 N Main St, Winsted, CT 06098
• 

  Est $309,826 Not Listed For Sale

  125 E Mountain Ave, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,622 Sq Ft
  • Built 1953

  125 E Mountain Ave, Winsted, CT 06098

  Last Sold Summary

  • 11% Above List Price
  • $173/SF
  • 39 Days On Market

  Last Sold Price $280,000

  Last Listing Agent David Sartirana Northwest CT Realty
• 

  $639,000 Sold Jul 31, 2025

  102 Hollow Hill Rd, Winsted, CT 06098

  • 3 Beds
  • 2.5 Baths
  • 2,692 Sq Ft
  • Built 2004

  Last Sold Summary

  • 8% Above List Price
  • $237/SF
  • 49 Days On Market

  Current Estimated Value $653,199

  Last Listing Agent Dawn Rousseau Showcase Realty, Inc.

  102 Hollow Hill Rd, Winsted, CT 06098
• 

  Est $279,695 Not Listed For Sale

  103 E Mountain Ave, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,304 Sq Ft
  • Built 1955

  103 E Mountain Ave, Winsted, CT 06098

  Last Sold Summary

  • 2% Above List Price
  • $211/SF
  • 29 Days On Market

  Last Sold Price $275,000

  Last Listing Agent David Merrigan Merrigan & Lefebvre Realty
• 

  $8,000 Sold May 16, 2025

  104 Norfolk Rd, Winsted, CT 06098

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

  Last Sold Summary

  • 79% Below List Price
  • $8/SF
  • 44 Days On Market

  Last Listing Agent David Sartirana Northwest CT Realty

  104 Norfolk Rd, Winsted, CT 06098
• 

  Est $626,951 Not Listed For Sale

  129 Forest Ave, Winsted, CT 06098

  • 3 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • Built 2007

  129 Forest Ave, Winsted, CT 06098

  Last Sold Summary

  • 6% Below List Price
  • $279/SF
  • 195 Days On Market

  Last Sold Price $670,000

  Last Listing Agent Daniel Burgio William Raveis Real Estate
• 

  $383,000 Sold Sep 10, 2025

  41 Lovely St, Winsted, CT 06098

  • 5 Beds
  • 2 Baths
  • 2,531 Sq Ft
  • Built 1910

  Last Sold Summary

  • 9% Above List Price
  • $151/SF
  • 39 Days On Market

  Current Estimated Value $379,121

  Last Listing Agent Mary Mary LeBlanc Realty

  41 Lovely St, Winsted, CT 06098
• 

  Est $324,254 Not Listed For Sale

  143 Mountain Rd, Winsted, CT 06098

  • 2 Beds
  • 1 Bath
  • 1,249 Sq Ft
  • Built 1920

  143 Mountain Rd, Winsted, CT 06098

  Last Sold Summary

  • 16% Above List Price
  • $223/SF
  • 92 Days On Market

  Last Sold Price $279,000

  Last Listing Agent Don Sciarretto Berkshire Hathaway Home Services
• 

  $370,000 Sold Nov 14, 2025

  166 Torringford St, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 2,024 Sq Ft
  • Built 1898

  Last Sold Summary

  • 3% Below List Price
  • $183/SF
  • 77 Days On Market

  Current Estimated Value $376,042

  Last Listing Agent Lana Van Valkenburgh Vision Real Estate

  166 Torringford St, Winsted, CT 06098
• 

  Est $217,726 Not Listed For Sale

  11 Orchard St, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,759 Sq Ft
  • Built 1900

  11 Orchard St, Winsted, CT 06098

  Last Sold Summary

  • 33% Above List Price
  • $93/SF
  • 19 Days On Market

  Last Sold Price $164,000

  Last Listing Agent Jonathan Gineo Silver and Oak Realty
• 

  $389,900 Sold Nov 06, 2025

  27 Thibault Ave, Winsted, CT 06098

  • 8 Beds
  • 5 Baths
  • 7,372 Sq Ft
  • Built 1900

  Last Sold Summary

  • 3% Below List Price
  • $53/SF
  • 57 Days On Market

  Last Listing Agent Cathy Macias Northwest CT Realty

  27 Thibault Ave, Winsted, CT 06098
• 

  Est $298,059 Not Listed For Sale

  303 E Wakefield Blvd, Winsted, CT 06098

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1986

  303 E Wakefield Blvd, Winsted, CT 06098

  Last Sold Summary

  • 8% Above List Price
  • $286/SF
  • 21 Days On Market

  Last Sold Price $275,000

  Last Listing Agent Tammy Schaller William Raveis Real Estate
• 

  $388,000 Sold Aug 27, 2025

  409 N Main St, Winsted, CT 06098

  • 5 Beds
  • 2 Baths
  • 2,403 Sq Ft
  • Built 1868

  Last Sold Summary

  • $161/SF
  • 70 Days On Market

  Current Estimated Value $378,037

  Last Listing Agent Christine Hunter Hunter Real Estate, LLC

  409 N Main St, Winsted, CT 06098
• 

  Est $271,717 Not Listed For Sale

  151 Hinsdale Ave, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,634 Sq Ft
  • Built 1948

  151 Hinsdale Ave, Winsted, CT 06098

  Last Sold Summary

  • 24% Above List Price
  • $135/SF
  • 154 Days On Market

  Last Sold Price $220,000

  Last Listing Agent Sarah Isabella Glenstone Real Estate LLC

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