Winchester, CT Homes

• 

  $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
• 

  Est $448,104 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,654 Sq Ft

  138 Mountain Rd, Winsted, CT 06098

  138 Mountain Rd, 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 $183,511

  Last Listing Agent Katie Breitkreutz Dave Jones Realty, LLC

  100 Norfolk Rd, Winsted, CT 06098
• 

  Est $274,070 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,135 Sq Ft

  152 Lincoln Ave, Winsted, CT 06098

  152 Lincoln Ave, 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
• 

  Est $934,443 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,379 Sq Ft

  342 Taylor Brook Rd, Winsted, CT 06098

  342 Taylor Brook Rd, 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

  Last Listing Agent Suzie Larson Turning Point Realty, LLC

  130 Alpha Ave, Winsted, CT 06098
• 

  Est $329,602 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,512 Sq Ft

  52 Overlook Rd, Winsted, CT 06098

  52 Overlook 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 $313,043

  Last Listing Agent David Sartirana Northwest CT Realty

  178 Boyd St, Winsted, CT 06098
• 

  Est $241,349 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  94 Stanton Ave, Winsted, CT 06098

  94 Stanton Ave, Winsted, CT 06098
• 

  $180,000 Sold Feb 10, 2025

  111 Riverton Rd Unit 7, Winsted, CT 06098

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

  Last Sold Summary

  • 5% Below List Price
  • $150/SF
  • 68 Days On Market

  Current Estimated Value $194,190

  Last Listing Agent David Sartirana Northwest CT Realty

  111 Riverton Rd Unit 7, Winsted, CT 06098
• 

  Est $393,529 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,177 Sq Ft

  129 Skinner Rd, Winsted, CT 06098

  129 Skinner Rd, 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
• 

  Est $286,747 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,282 Sq Ft

  90 Colony Dr, Winsted, CT 06098

  90 Colony Dr, 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
• 

  Est $561,826 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 816 Sq Ft

  756 Lake Dr, Winsted, CT 06098

  756 Lake Dr, 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
• 

  Est $365,584 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,774 Sq Ft

  230 Boyd St, Winsted, CT 06098

  230 Boyd St, 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
• 

  Est $1,415,654 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,526 Sq Ft

  552 E Wakefield Blvd, Winsted, CT 06098

  552 E Wakefield Blvd, Winsted, 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
• 

  Est $277,212 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,504 Sq Ft

  270 Holabird Ave, Winsted, CT 06098

  270 Holabird Ave, 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
• 

  Est $329,641 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,872 Sq Ft

  2 Herman Rd, Winsted, CT 06098

  2 Herman Rd, 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
• 

  Est $270,406 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,132 Sq Ft

  445 N Main St, Winsted, CT 06098

  445 N Main St, 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 $368,755

  Last Listing Agent Roberta LeJeune Marrin Santore Realty LLC

  113 Preston Rd, Winsted, CT 06098
• 

  Est $545,692 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,322 Sq Ft

  339 W Wakefield Blvd, Winsted, CT 06098

  339 W 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 $1,315,825

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

  435 W Wakefield Blvd, Winsted, CT 06098
• 

  Est $289,001 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,966 Sq Ft

  31 Cottage St, Winsted, CT 06098

  31 Cottage St, 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
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  Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 880 Sq Ft

  53 Overlook Rd, Winsted, CT 06098

  53 Overlook Rd, 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
• 

  Est $264,405 Not Listed For Sale

  • 7 Beds
  • 2 Baths
  • 2,446 Sq Ft

  20 Center St, Winsted, CT 06098

  20 Center 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 $199,045

  Last Listing Agent Sandra Marchetti The Washington Agency

  111 Riverton Rd Unit 37, Winsted, CT 06098
• 

  Est $229,456 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,242 Sq Ft

  31 Hurlbut St, Winsted, CT 06098

  31 Hurlbut St, 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 $112,804

  Last Listing Agent David Sartirana Northwest CT Realty

  11 Gibbs St Unit 9, Winsted, CT 06098
• 

  Est $262,770 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,972 Sq Ft

  341 N Main St, Winsted, CT 06098

  341 N Main St, 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
• 

  Est $346,897 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,880 Sq Ft

  139 Forest Ave, Winsted, CT 06098

  139 Forest Ave, Winsted, CT 06098

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