Winchester, CT Homes

• 

  Est $222,816 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,600 Sq Ft

  17 Front St, Winsted, CT 06098

  17 Front St, Winsted, CT 06098
• 

  

  

  /34

  $749,900

  • 7 Beds
  • 3 Baths
  • 3,486 Sq Ft

  39 S Main St, Winsted, CT 06098

  THREE PROPERTIES ONE PRICE!!! Includes single family, multi family & additional lot totaling 4.36 acres. 1. 3500 sq ft 2 family home featuring 1800's architecture including massive period correct windows, wrap around porch, beautiful stone foundation, and detached 2 car garage. 5 bed, 2 1/2 bath main house with 2 bed, 1 bath attic apartment, freshly updated. Brand new whole house natural gas

  Ryan Horvay Smith & DeGroat Real Estate

  39 S Main St, Winsted, CT 06098
• 

  $679,000 Sold Apr 30, 2025

  110 South Rd, Winsted, CT 06098

  • 4 Beds
  • 3 Baths
  • 3,870 Sq Ft
  • Built 1984

  Last Sold Summary

  • $175/SF
  • 5 Days On Market

  Current Estimated Value $695,343

  Last Listing Agent Matthew Egan Regency Real Estate, LLC

  110 South Rd, Winsted, CT 06098
• 

  Est $441,000 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,969 Sq Ft

  319 Taylor Brook Rd, Winsted, CT 06098

  319 Taylor Brook Rd, Winsted, CT 06098
• 

  

  

  /5

  $158,000

  • Land
  • 1.18 Acres
  • $133,898 per Acre

  843-845 (lots - 10A, E Wakefield Blvd, Winchester, CT 06098

  1.18 Acre ,Approximately 201 Ft Road fro . ntage )Lightly wooded E. Wakefield Blvd. lot located at the end of 3rd Bay . Panoramic view overlooking the length or lake. Survey , Zoning HL regulations and Deed are available , and Access is also available off E. Mtn Road . Survey shows Town of Winchester parcel with warterfront access Rare opportunity to build your dream home . , SELLER WILL

  David D'Amore Northwest CT Realty

  843-845 (lots - 10A, E Wakefield Blvd, Winchester, CT 06098
• 

  $326,000 Sold Oct 31, 2025

  62 Fruit St Unit 64, Winsted, CT 06098

  • 6 Beds
  • 2 Baths
  • 3,078 Sq Ft
  • Built 1902

  Last Sold Summary

  • $106/SF
  • 13 Days On Market

  Current Estimated Value $305,464

  Last Listing Agent Antonio De La Cruz Eagle Eye Realty PLLC

  62 Fruit St Unit 64, Winsted, CT 06098
• 

  Est $266,631 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,500 Sq Ft

  39 Rockwell St, Winsted, CT 06098

  39 Rockwell St, Winsted, CT 06098
• 

  

  /31

  $164,000

  • 2 Beds
  • 1.5 Baths
  • 992 Sq Ft

  35 Riveredge Dr Unit 35, Winsted, CT 06098

  Charming Riverview Townhouse with Patio Enjoy easy living in this well-located two-bedroom townhouse set on a slab and overlooking the river. The main level features a living room, dining room, and functional kitchen, perfect for everyday comfort and entertaining. Sliding glass doors lead to a private patio where you can relax and enjoy the peaceful water views. Upstairs offers two comfortable

  Joanne Donne The Washington Agency

  35 Riveredge Dr Unit 35, Winsted, CT 06098
• 

  $380,000 Sold Sep 17, 2025

  226 E Wakefield Blvd, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,196 Sq Ft
  • Built 1974

  Last Sold Summary

  • 3% Above List Price
  • $318/SF
  • 38 Days On Market

  Current Estimated Value $381,283

  Last Listing Agent Pascale Nejaime William Pitt Sotheby's Int'l

  226 E Wakefield Blvd, Winsted, CT 06098
• 

  Est $277,155 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,114 Sq Ft

  160 Glendale Ave, Winsted, CT 06098

  160 Glendale Ave, Winsted, CT 06098
• 

  /2

  $39,900 Pending

  • Land
  • 0.92 Acre
  • $43,370 per Acre

  256 Colebrook Rd, Winchester Center, CT 06098

  Just under an acre of land and over 100 feet of road frontage available on Colebrook Road!

  Austin Brochu Sullivan Real Estate Inc

  256 Colebrook Rd, Winchester Center, CT 06098
• 

  $135,000 Sold Mar 27, 2025

  13 Riveredge Dr Unit 13, Winsted, CT 06098

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

  Last Sold Summary

  • 4% Below List Price
  • $210/SF
  • 72 Days On Market

  Current Estimated Value $136,902

  Last Listing Agent James Bradshaw Berkshire Hathaway NE Prop.

  13 Riveredge Dr Unit 13, Winsted, CT 06098
• 

  Est $310,022 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,544 Sq Ft

  153 Mathew Rd, Winsted, CT 06098

  153 Mathew Rd, Winsted, CT 06098
• 

  

  /38

  $395,000

  • 3 Beds
  • 1.5 Baths
  • 1,909 Sq Ft

  720 Main St, Winsted, CT 06098

  Prime Mixed-Use Opportunity in Downtown Winsted! High-visibility two-story building located on bustling Main Street, most recently home to "JT's Cafe," and previously known as "The Winning Ticket Cafe." The first-floor commercial space includes features such as an existing kitchen area with oven range vents, fridge, bathroom, and open seating area. Great potential for a new restaurant, cafe,

  Ryan Marconi The Washington Agency

  720 Main St, Winsted, CT 06098
• 

  $236,434 Sold Aug 25, 2025

  343 W Wakefield Blvd, Winsted, CT 06098

  • 2 Beds
  • 1 Bath
  • 674 Sq Ft
  • Built 1923

  Last Sold Summary

  • 15% Below List Price
  • $351/SF
  • 40 Days On Market

  Current Estimated Value $249,004

  Last Listing Agent Patrick Precourt Meridian Realty Group LLC

  343 W Wakefield Blvd, Winsted, CT 06098
• 

  Est $207,261 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,626 Sq Ft

  111 Torringford St Unit 19, Winsted, CT 06098

  111 Torringford St Unit 19, Winsted, CT 06098
• 

  /2

  $69,000

  • Land
  • 2 Acres
  • $34,500 per Acre

  503 N Main St, Winsted, CT 06098

  Prime Building Lot Near Downtown & Highland Lake-Discover the perfect setting for your dream home on this 2 acre lot at 503 N Main Street. The Property has over 500' of road frontage, permitted uses include; accessory residential uses, family day care home, farm, seasonal cottages, single family dwelling. The property offers a peaceful atmosphere while maintaining easy access to downtown

  Charles Albertario William Raveis Real Estate

  503 N Main St, Winsted, CT 06098
• 

  $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 $147,283

  Last Listing Agent Kristen Duchene Litchfield County Real Estate

  9 Loomis St, Winsted, CT 06098
• 

  Est $216,411 Not Listed For Sale

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

  111 Riverton Rd Unit 30, Winsted, CT 06098

  111 Riverton Rd Unit 30, Winsted, CT 06098
• 

  

  /23

  $230,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 1,172 Sq Ft

  9 John St, Winsted, CT 06098

  Beautifully renovated 1870 Colonial offering 1,172 sq. ft. of updated and functional living space. The home features hardwood floors in the living room and both bedrooms, adding warmth and durability throughout. A convenient first-floor bedroom provides flexibility, while the spacious primary bedroom is located on the second level. The kitchen has been completely refreshed with new flooring,

  Michael Grady William Raveis Real Estate

  9 John 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 $309,572

  Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

  17 Adams St, Winsted, CT 06098
• 

  Est $299,949 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,982 Sq Ft

  182 Florence St, Winsted, CT 06098

  182 Florence St, Winsted, CT 06098
• 

  

  /13

  $649,900 Pending

  • Land
  • 41.23 Acres
  • $15,763 per Acre

  115 Old Robertsville Rd, Winsted, CT 06098

  Development Opportunity! 41.23 Acres with Historic Home & Barn - Subdivision Possible Rare chance to own a prime 41.23-acre parcel in New England with an 1800 Antique Colonial Farmhouse and classic English/New England hybrid barn. The land may be subdividable and is located near the highly desirable Riverwalk Condominiums, making it ideal for new condo development (subject to approvals). The home

  Jared Tedesco Litchfield County Real Estate

  115 Old Robertsville Rd, 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 $276,820 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,180 Sq Ft

  36 Charles St, Winsted, CT 06098

  36 Charles St, Winsted, CT 06098
• 

  /2

  $250,000

  • 4 Beds
  • 2 Baths
  • 1,874 Sq Ft

  107 Birdsall St, Winsted, CT 06098

  Spacious colonial with 4 bedrooms, 2 full baths, generous size living room, dining room, sitting room, sunroom. Looking for space, this home definitely has it. Harwood floors thorough, granite countertops, marble backsplash, Island in kitchen. Short walk to highland Lake With a little TLC this home will be a GEM! Home being sold AS-IS.

  Jesica Beaulieu Dave Jones Realty, LLC

  107 Birdsall St, 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 $281,721

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

  325 E Wakefield Blvd, Winsted, CT 06098
• 

  Est $204,201 Not Listed For Sale

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

  111 Riverton Rd Unit 88, Winsted, CT 06098

  111 Riverton Rd Unit 88, Winsted, CT 06098
• 

  

  /14

  $450,000 Under Contract

  • Land
  • 160 Acres
  • $2,812 per Acre

  430 Smith Hill Rd, Colebrook, CT 06021

  A rare opportunity to create your own private retreat in the peaceful foothills of Colebrook. Includes 18.7 acres of buildable land with the possibility to subdivide into two parcels, giving you options for your dream home or future investment. Tucked well off the beaten path, the setting is surrounded by natural beauty, offering unmatched privacy and a sense of seclusion. With selective

  Rodney Motta Berkshire Hathaway NE Prop.

  430 Smith Hill Rd, Colebrook, CT 06021
• 

  $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

  Last Listing Agent Terence Dominick Exceptional Real Estate LLC

  22 Curtice St, Winsted, CT 06098
• 

  Est $377,786 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,594 Sq Ft

  133 E Wakefield Blvd, Winsted, CT 06098

  133 E Wakefield Blvd, Winsted, CT 06098
• 

  

  /12

  $170,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 992 Sq Ft

  21 Riveredge Dr Unit 21, Winsted, CT 06098

  Updated 2-bedroom, 1.5-bath condo featuring a renovated kitchen with new appliances (2022), smart thermostats, and a newly updated shower including new plumbing (2024). Enjoy oversized sliders in the living room leading to a paved, private patio overlooking the Still River-perfect for relaxing or entertaining. With just a fresh coat of paint and your personal design touch, this home is ready to

  Jennifer Mitchell Northwest CT Realty

  21 Riveredge Dr Unit 21, Winsted, CT 06098
• 

  $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 $251,299

  Last Listing Agent Jill Menard Realty One Group Cutting Edge

  115 Laurel Way, Winsted, CT 06098
• 

  Est $280,630 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,490 Sq Ft

  257 Walnut St, Winsted, CT 06098

  257 Walnut St, Winsted, CT 06098
• 

  

  /21

  $879,990

  • Land
  • 131.5 Acres
  • $6,692 per Acre

  000000 Norfolk Rd, Winchester, CT 06098

  Rare Multi-Parcel Land Opportunity - 5 Parcels, Endless Possibilities Discover this exceptional assemblage of five contiguous parcels spanning the scenic towns of Winchester and Colebrook in Connecticut's pristine Litchfield County. This remarkable offering combines the best of both worlds with a captivating mixture of open fields and mature forest, creating a diverse landscape that's as

  John Harney William Pitt Sotheby's Int'l

  000000 Norfolk Rd, Winchester, CT 06098
• 

  $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 $312,602 Not Listed For Sale

  • 5 Beds
  • 2,820 Sq Ft

  204 Gilbert Ave, Winsted, CT 06098

  204 Gilbert Ave, Winsted, CT 06098
• 

  /2

  $59,900

  • Land
  • 0.41 Acre
  • $146,098 per Acre

  105,107 E Mountain Rd, Winchester, CT 06098

  105 & 107 Mountain Road parcels are contiguous and located on a dirt road . . Deed indicates right of way to Highland lake water frontage within walking distance. See documents attached for Deed , Site plan, Peculation tests , Survey and Septic testing available . Possible city sewer access at buyers expense . Seller will consider financing with a minimum of 15% DOWN PAYMENT FOR A 2 YEAR BALLOON

  David D'Amore Northwest CT Realty

  105,107 E Mountain Rd, Winchester, CT 06098
• 

  $135,000 Sold Feb 28, 2025

  234 E Wakefield Blvd, Winsted, CT 06098

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft
  • Built 1939

  Last Sold Summary

  • 17% Above List Price
  • $165/SF
  • 3 Days On Market

  Current Estimated Value $145,365

  Last Listing Agent Jeffrey Liskin Northwest CT Realty

  234 E Wakefield Blvd, Winsted, CT 06098
• 

  Est $211,639 Not Listed For Sale

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

  111 Riverton Rd Unit 53, Winsted, CT 06098

  111 Riverton Rd Unit 53, Winsted, CT 06098

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