Recently Sold Winchester, CT Homes

• 

  $379,000 Sold May 09, 2025

  244 Colebrook Rd, Winsted, CT 06098

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

  Last Sold Summary

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

  Current Estimated Value $377,851

  Last Listing Agent Carol York For Sale By Owner Connecticut

  244 Colebrook Rd, Winsted, CT 06098
• 

  $281,000 Sold Aug 13, 2025

  711 W Wakefield Blvd, Winchester Center, CT 06098

  • Land
  • 0.61 Acre
  • $460,656 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 371 Days On Market

  Current Estimated Value $267,333

  Last Listing Agent Peter Kores The Washington Agency

  711 W Wakefield Blvd, Winchester Center, CT 06098
• 

  $270,000 Sold Sep 25, 2025

  22 Stanton Ave, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,058 Sq Ft
  • Built 1900

  Last Sold Summary

  • 2% Above List Price
  • $255/SF
  • 25 Days On Market

  Current Estimated Value $269,813

  Last Listing Agent Jeffrey Liskin Northwest CT Realty

  22 Stanton Ave, Winsted, CT 06098
• 

  $160,000 Sold Mar 10, 2026

  21 Riveredge Dr Unit 21, Winsted, CT 06098

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

  Last Sold Summary

  • 6% Below List Price
  • $161/SF
  • 19 Days On Market

  Current Estimated Value $164,532

  Last Listing Agent Jennifer Mitchell Northwest CT Realty

  21 Riveredge Dr Unit 21, Winsted, CT 06098
• 

  $231,000 Sold Feb 20, 2026

  817 E Wakefield Blvd, Winsted, CT 06098

  • 2 Beds
  • 1 Bath
  • 1,051 Sq Ft
  • Built 1930

  Last Sold Summary

  • 3% Above List Price
  • $220/SF
  • 53 Days On Market

  Current Estimated Value $290,720

  Last Listing Agent George Sznaj DB Associates of CT, LLC

  817 E Wakefield Blvd, Winsted, CT 06098
• 

  $172,500 Sold Aug 25, 2025

  415 N Main St, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,446 Sq Ft
  • Built 1900

  Last Sold Summary

  • 11% Below List Price
  • $119/SF
  • 43 Days On Market

  Current Estimated Value $199,895

  Last Listing Agent Jeffrey Liskin Northwest CT Realty

  415 N Main St, Winsted, CT 06098
• 

  $330,000 Sold Sep 24, 2025

  50 Manchester Heights, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,287 Sq Ft
  • Built 1953

  Last Sold Summary

  • 1% Below List Price
  • $256/SF
  • 118 Days On Market

  Current Estimated Value $319,679

  Last Listing Agent Lisa Bredice Coldwell Banker Realty

  50 Manchester Heights, Winsted, CT 06098
• 

  $275,000 Sold Sep 21, 2025

  920 Main St, Winsted, CT 06098

  • 6 Beds
  • 4 Baths
  • 4,635 Sq Ft
  • Built 1900

  Last Sold Summary

  • 54% Above List Price
  • $59/SF
  • 0 Days On Market

  Last Listing Agent Melissa Kiehl KW Legacy Partners

  920 Main St, Winsted, CT 06098
• 

  $270,000 Sold Dec 02, 2025

  101 Norfolk Rd, Winsted, CT 06098

  • 2 Beds
  • 1 Bath
  • 1,880 Sq Ft
  • Built 1990

  Last Sold Summary

  • 14% Below List Price
  • $144/SF
  • 68 Days On Market

  Current Estimated Value $275,517

  Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

  101 Norfolk Rd, Winsted, CT 06098
• 

  $30,000 Sold Feb 20, 2026

  52 White St, Winsted, CT 06098

  • Land
  • 1.88 Acres
  • $15,957 per Acre

  Last Sold Summary

  • 3% Above List Price
  • 75 Days On Market

  Last Listing Agent David Sartirana Northwest CT Realty

  52 White St, Winsted, CT 06098
• 

  $410,000 Sold Jul 31, 2025

  17 Woodland Ave, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 2,105 Sq Ft
  • Built 1938

  Last Sold Summary

  • 2% Below List Price
  • $195/SF
  • 39 Days On Market

  Current Estimated Value $418,126

  Last Listing Agent Vincent DeVico Showcase Realty, Inc.

  17 Woodland Ave, Winsted, CT 06098
• 

  $378,000 Sold Jul 07, 2025

  Unlisted Address

  • 4 Beds
  • 3 Baths
  • 1,786 Sq Ft
  • Built 1988

  Last Sold Summary

  • 3% Above List Price
  • $212/SF
  • 3 Days On Market

  Current Estimated Value $388,490

  Last Listing Agent David Sartirana Northwest CT Realty

  Unlisted Address
• 

  $150,000 Sold Mar 10, 2026

  8 Oak St, Winsted, CT 06098

  • 2 Beds
  • 1.5 Baths
  • 832 Sq Ft
  • Built 1900

  Last Sold Summary

  • 21% Below List Price
  • $180/SF
  • 41 Days On Market

  Current Estimated Value $157,335

  Last Listing Agent Austin Brochu Sullivan Real Estate Inc

  8 Oak St, Winsted, CT 06098
• 

  $475,000 Sold Feb 26, 2026

  197 Spencer Hill Rd, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 2,167 Sq Ft
  • Built 1986

  Last Sold Summary

  • 5% Below List Price
  • $219/SF
  • 129 Days On Market

  Current Estimated Value $490,951

  Last Listing Agent David Sartirana Northwest CT Realty

  197 Spencer Hill Rd, Winsted, CT 06098
• 

  $275,000 Sold Apr 23, 2025

  151 Elm St, Winsted, CT 06098

  • 5 Beds
  • 2 Baths
  • 2,191 Sq Ft
  • Built 1880

  Last Sold Summary

  • 2% Below List Price
  • $126/SF
  • 41 Days On Market

  Current Estimated Value $288,923

  Last Listing Agent Jeffrey Liskin Northwest CT Realty

  151 Elm St, Winsted, CT 06098
• 

  $325,000 Sold Jul 17, 2025

  284 Gilbert Ave, Winsted, CT 06098

  • 4 Beds
  • 1 Bath
  • 1,849 Sq Ft
  • Built 1956

  Last Sold Summary

  • 2% Above List Price
  • $176/SF
  • 40 Days On Market

  Current Estimated Value $328,556

  Last Listing Agent David Sartirana Northwest CT Realty

  284 Gilbert Ave, Winsted, CT 06098
• 

  $160,000 Sold Jul 18, 2025

  100 Norfolk Rd, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 2,914 Sq Ft
  • Built 1947

  Last Sold Summary

  • 9% Below List Price
  • $55/SF
  • 8 Days On Market

  Current Estimated Value $182,416

  Last Listing Agent Katie Breitkreutz Dave Jones Realty, LLC

  100 Norfolk Rd, Winsted, CT 06098
• 

  $345,000 Sold Oct 31, 2025

  115 Wallens St, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 2,100 Sq Ft
  • Built 1962

  Last Sold Summary

  • 38% Above List Price
  • $164/SF
  • 27 Days On Market

  Current Estimated Value $326,220

  Last Listing Agent Heidi Picard-Ramsay Berkshire Hathaway NE Prop.

  115 Wallens St, Winsted, CT 06098
• 

  $29,000 Sold Nov 11, 2025

  130 Alpha Ave, Winsted, CT 06098

  • Land
  • 0.41 Acre
  • $70,732 per Acre

  Last Sold Summary

  • 47% Below List Price
  • 119 Days On Market

  Current Estimated Value $131,333

  Last Listing Agent Suzie Larson Turning Point Realty, LLC

  130 Alpha Ave, Winsted, CT 06098
• 

  $375,000 Sold Feb 05, 2026

  117 South Rd, Winsted, CT 06098

  • 3 Beds
  • 3 Baths
  • 2,747 Sq Ft
  • Built 1955

  Last Sold Summary

  • 29% Below List Price
  • $137/SF
  • 230 Days On Market

  Current Estimated Value $468,531

  Last Listing Agent Christina Niziolek William Raveis Real Estate

  117 South Rd, Winsted, CT 06098
• 

  $305,000 Sold Apr 07, 2025

  178 Boyd St, Winsted, CT 06098

  • 5 Beds
  • 2 Baths
  • 1,826 Sq Ft
  • Built 1900

  Last Sold Summary

  • 2% Above List Price
  • $167/SF
  • 62 Days On Market

  Current Estimated Value $311,143

  Last Listing Agent David Sartirana Northwest CT Realty

  178 Boyd St, Winsted, CT 06098
• 

  $395,000 Sold Apr 08, 2025

  47 Orchard St, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 1,818 Sq Ft
  • Built 1875

  Last Sold Summary

  • 16% Below List Price
  • $217/SF
  • 106 Days On Market

  Current Estimated Value $405,058

  Last Listing Agent Bryan Palladino Showcase Realty, Inc.

  47 Orchard St, Winsted, CT 06098
• 

  $135,800 Sold Dec 15, 2025

  38 Riveredge Dr Unit 38, Winsted, CT 06098

  • 1 Bed
  • 1 Bath
  • 635 Sq Ft
  • Built 1986

  Last Sold Summary

  • 9% Below List Price
  • $214/SF
  • 10 Days On Market

  Current Estimated Value $134,566

  Last Listing Agent Suzie Larson Turning Point Realty, LLC

  38 Riveredge Dr Unit 38, Winsted, CT 06098
• 

  $370,000 Sold Jul 21, 2025

  203 Holabird Ave, Winchester Center, CT 06098

  • 5 Beds
  • 4 Baths
  • 3,690 Sq Ft
  • Built 1890

  Last Sold Summary

  • $100/SF
  • 6 Days On Market

  Current Estimated Value $369,712

  Last Listing Agent Ryan Horvay Smith & DeGroat Real Estate

  203 Holabird Ave, Winchester Center, CT 06098
• 

  $310,000 Sold Oct 03, 2025

  36 Whiting St, Winsted, CT 06098

  • 3 Beds
  • 2.5 Baths
  • 1,608 Sq Ft
  • Built 1917

  Last Sold Summary

  • 3% Above List Price
  • $193/SF
  • 37 Days On Market

  Current Estimated Value $306,845

  Last Listing Agent Brandon Riley eXp Realty

  36 Whiting St, Winsted, CT 06098
• 

  $250,000 Sold Jan 23, 2026

  174 Wallens St Unit B6, Winsted, CT 06098

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft
  • Built 2008

  Last Sold Summary

  • 2% Above List Price
  • $185/SF
  • 4 Days On Market

  Last Listing Agent David Sartirana Northwest CT Realty

  174 Wallens St Unit B6, Winsted, CT 06098
• 

  $250,000 Sold Mar 01, 2026

  43 Wallens St, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 1,971 Sq Ft
  • Built 1900

  Last Sold Summary

  • 9% Below List Price
  • $127/SF
  • 5 Days On Market

  Current Estimated Value $270,375

  Last Listing Agent Kristen Duchene Litchfield County Real Estate

  43 Wallens St, Winsted, CT 06098
• 

  $425,000 Sold Oct 28, 2025

  548 E Wakefield Blvd, Winsted, CT 06098

  • 2 Beds
  • 1 Bath
  • 512 Sq Ft
  • Built 1936

  Last Sold Summary

  • 8% Above List Price
  • $830/SF
  • 60 Days On Market

  Current Estimated Value $424,812

  Last Listing Agent Amy Rio Executive Real Estate Inc.

  548 E Wakefield Blvd, Winsted, CT 06098
• 

  $1,215,000 Sold Sep 10, 2025

  435 W Wakefield Blvd, Winsted, CT 06098

  • 8 Beds
  • 4.5 Baths
  • 5,231 Sq Ft
  • Built 1930

  Last Sold Summary

  • 29% Below List Price
  • $232/SF
  • 347 Days On Market

  Current Estimated Value $1,318,318

  Last Listing Agent Heidi Picard-Ramsay Berkshire Hathaway NE Prop.

  435 W Wakefield Blvd, Winsted, CT 06098
• 

  $240,000 Sold Sep 09, 2025

  42 Maloney Ct, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Built 1956

  Last Sold Summary

  • 4% Below List Price
  • $238/SF
  • 6 Days On Market

  Current Estimated Value $242,048

  Last Listing Agent James Walsh James Walsh

  42 Maloney Ct, Winsted, CT 06098
• 

  $330,000 Sold Mar 10, 2026

  157 Elm St, Winsted, CT 06098

  • 6 Beds
  • 2.5 Baths
  • 2,376 Sq Ft
  • Built 1900

  Last Sold Summary

  • 3% Below List Price
  • $139/SF
  • 65 Days On Market

  Current Estimated Value $332,460

  Last Listing Agent Doreen Gagnon Coldwell Banker Realty

  157 Elm St, Winsted, CT 06098
• 

  $198,000 Sold Oct 28, 2025

  111 Riverton Rd Unit 37, Winsted, CT 06098

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

  Last Sold Summary

  • $164/SF
  • 48 Days On Market

  Current Estimated Value $199,573

  Last Listing Agent Sandra Marchetti The Washington Agency

  111 Riverton Rd Unit 37, Winsted, CT 06098
• 

  $113,000 Sold Jun 23, 2025

  11 Gibbs St Unit 9, Winsted, CT 06098

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

  Last Sold Summary

  • 3% Above List Price
  • $198/SF
  • 10 Days On Market

  Current Estimated Value $115,959

  Last Listing Agent David Sartirana Northwest CT Realty

  11 Gibbs St Unit 9, Winsted, CT 06098
• 

  $309,250 Sold Feb 06, 2026

  107 Peck Rd, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1983

  Last Sold Summary

  • 9% Below List Price
  • $322/SF
  • 54 Days On Market

  Current Estimated Value $310,238

  Last Listing Agent Rebecca Doh W. Raveis Lifestyles Realty

  107 Peck Rd, Winsted, CT 06098
• 

  $282,000 Sold Jul 16, 2025

  88 Strong Terrace, Winsted, CT 06098

  • 5 Beds
  • 1.5 Baths
  • 2,470 Sq Ft
  • Built 1890

  Last Sold Summary

  • 3% Below List Price
  • $114/SF
  • 10 Days On Market

  Current Estimated Value $296,855

  Last Listing Agent Austin Brochu Sullivan Real Estate Inc

  88 Strong Terrace, Winsted, CT 06098
• 

  $1,200,000 Sold Jul 23, 2025

  200 Perch Rock Trail, Winsted, CT 06098

  • 3 Beds
  • 2.5 Baths
  • 2,407 Sq Ft
  • Built 1948

  Last Sold Summary

  • 21% Above List Price
  • $499/SF
  • 0 Days On Market

  Current Estimated Value $1,212,635

  Last Listing Agent Annie Simard LPT Realty

  200 Perch Rock Trail, Winsted, CT 06098
• 

  $440,000 Sold Oct 29, 2025

  159 Sandy Brook Rd, Colebrook, CT 06021

  • 4 Beds
  • 1.5 Baths
  • 1,940 Sq Ft
  • Built 1800

  Last Sold Summary

  • 11% Below List Price
  • $227/SF
  • 73 Days On Market

  Current Estimated Value $441,451

  Last Listing Agent Lenore Mallett William Pitt Sotheby's Int'l

  159 Sandy Brook Rd, Colebrook, CT 06021
• 

  $70,000 Sold May 01, 2025

  50-52 Cottage St, Winchester, CT 06098

  • 5 Beds
  • 2,016 Sq Ft
  • Built 1800

  Last Sold Summary

  • 79% Above List Price
  • $35/SF
  • 18 Days On Market

  Last Listing Agent David Sartirana Northwest CT Realty

  50-52 Cottage St, Winchester, CT 06098
• 

  $314,000 Sold Jul 03, 2025

  150 Mathew Rd, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,480 Sq Ft
  • Built 1979

  Last Sold Summary

  • 10% Below List Price
  • $212/SF
  • 64 Days On Market

  Current Estimated Value $318,579

  Last Listing Agent Josh Dionne Commercial Services Realty

  150 Mathew Rd, Winsted, CT 06098
• 

  $120,000 Sold Jul 08, 2025

  11 Gibbs St Unit 7, Winsted, CT 06098

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft
  • Built 1984

  Last Sold Summary

  • 9% Above List Price
  • $211/SF
  • 3 Days On Market

  Current Estimated Value $119,880

  Last Listing Agent David Sartirana Northwest CT Realty

  11 Gibbs St Unit 7, Winsted, CT 06098

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