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 $376,471

  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 $278,333

  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 $270,242

  Last Listing Agent Jeffrey Liskin Northwest CT Realty

  22 Stanton Ave, Winsted, CT 06098
• 

  $288,000 Sold Feb 14, 2025

  86 Strong Terrace, Winsted, CT 06098

  • 5 Beds
  • 1.5 Baths
  • 1,646 Sq Ft
  • Built 1880

  Last Sold Summary

  • $175/SF
  • 69 Days On Market

  Current Estimated Value $309,457

  Last Listing Agent Lindsay J. Warner Tier 1 Real Estate

  86 Strong Terrace, 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 $184,735

  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 $321,434

  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

  Current Estimated Value $352,664

  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

  Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

  101 Norfolk Rd, 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 $414,256

  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 $382,190

  Last Listing Agent David Sartirana Northwest CT Realty

  Unlisted Address
• 

  $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 $287,910

  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 $328,080

  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 $319,558

  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 $130,333

  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

  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 $297,161

  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 $394,110

  Last Listing Agent Bryan Palladino Showcase Realty, Inc.

  47 Orchard St, Winsted, CT 06098
• 

  $268,000 Sold Mar 18, 2025

  86 Maple St, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 1,428 Sq Ft
  • Built 1880

  Last Sold Summary

  • 11% Below List Price
  • $188/SF
  • 128 Days On Market

  Current Estimated Value $273,149

  Last Listing Agent Chris LaCava Coldwell Banker Realty

  86 Maple 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

  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 $367,684

  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 $305,622

  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
• 

  $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 $425,637

  Last Listing Agent Amy Rio Executive Real Estate Inc.

  548 E Wakefield Blvd, Winsted, CT 06098
• 

  $343,000 Sold Feb 14, 2025

  113 Preston Rd, Winsted, CT 06098

  • 2 Beds
  • 2 Baths
  • 1,566 Sq Ft
  • Built 1993

  Last Sold Summary

  • 6% Above List Price
  • $219/SF
  • 53 Days On Market

  Current Estimated Value $375,047

  Last Listing Agent Roberta LeJeune Marrin Santore Realty LLC

  113 Preston Rd, 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 $1,315,825

  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 $240,720

  Last Listing Agent James Walsh James Walsh

  42 Maloney Ct, Winsted, CT 06098
• 

  $395,000 Sold Mar 28, 2025

  102 Sunny Ridge Dr, Winsted, CT 06098

  • 3 Beds
  • 2.5 Baths
  • 1,792 Sq Ft
  • Built 1990

  Last Sold Summary

  • 1% Below List Price
  • $220/SF
  • 25 Days On Market

  Current Estimated Value $402,619

  Last Listing Agent David Sartirana Northwest CT Realty

  102 Sunny Ridge Dr, 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 $199,045

  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 $114,744

  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

  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 $292,262

  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 $1,178,206

  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 $452,466

  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 $308,878

  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 $118,213

  Last Listing Agent David Sartirana Northwest CT Realty

  11 Gibbs St Unit 7, Winsted, CT 06098
• 

  $275,000 Sold Sep 13, 2025

  179 Gilbert Ave, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,744 Sq Ft
  • Built 1981

  Last Sold Summary

  • 6% Above List Price
  • $158/SF
  • 46 Days On Market

  Current Estimated Value $276,225

  Last Listing Agent David Sartirana Northwest CT Realty

  179 Gilbert Ave, Winsted, CT 06098
• 

  $157,500 Sold Jun 26, 2025

  19 Riveredge Dr Unit 19, Winsted, CT 06098

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

  Last Sold Summary

  • 2% Below List Price
  • $159/SF
  • 3 Days On Market

  Current Estimated Value $159,611

  Last Listing Agent Maria Smith KW Legacy Partners

  19 Riveredge Dr Unit 19, Winsted, CT 06098
• 

  $2,200,000 Sold Oct 21, 2025

  381 Smith Hill Rd, Colebrook, CT 06021

  • 4 Beds
  • 3.5 Baths
  • 4,327 Sq Ft
  • Built 1795

  Last Sold Summary

  • $508/SF
  • 28 Days On Market

  Last Listing Agent Elvia Gignoux William Pitt Sotheby's Int'l

  381 Smith Hill Rd, Colebrook, CT 06021

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