Winchester, CT Homes

• 

  Est $353,683 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 920 Sq Ft

  103 Shore Dr, Winsted, CT 06098

  103 Shore Dr, 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
• 

  $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

  Last Listing Agent Antonio De La Cruz Eagle Eye Realty PLLC

  62 Fruit St Unit 64, Winsted, CT 06098
• 

  Est $305,542 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,104 Sq Ft

  139 Boyd St, Winsted, CT 06098

  139 Boyd St, Winsted, CT 06098
• 

  

  /2

  $299,900

  • Land
  • 30 Acres
  • $9,997 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
• 

  $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 $238,522 Not Listed For Sale

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

  174 Wallens St Unit D2, Winsted, CT 06098

  174 Wallens St Unit D2, 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
• 

  $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 $137,676

  Last Listing Agent James Bradshaw Berkshire Hathaway NE Prop.

  13 Riveredge Dr Unit 13, Winsted, CT 06098
• 

  Est $240,771 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 1,334 Sq Ft

  174 Wallens St Unit D1, Winsted, CT 06098

  174 Wallens St Unit D1, Winsted, CT 06098
• 

  

  /40

  $2,199,000

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

  431 W Wakefield Blvd, Winsted, CT 06098

  LOCAL NEWS JUST ANNOUNCED THAT WINSTED WAS 1 OF THE MOST DESIRABLE TOWNS TO LIVE WITH EMPHASIS ON BEAUTIFUL HIGHLAND LAKE. This waterfront estate at 431 W. Wakefield Blvd in Winchester, CT, is not just a home but the ultimate Highland Lake lifestyle. Imagine waking up each day to stunning lake views, with endless seasonal activities awaiting just beyond your doorstep. In the summer, dive into

  Lisa Ogren Berkshire Hathaway NE Prop.

  431 W Wakefield Blvd, 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 $243,622

  Last Listing Agent Patrick Precourt Dorrance Realty

  343 W Wakefield Blvd, Winsted, CT 06098
• 

  Est $284,322 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,946 Sq Ft

  174 Wallens St Unit C3, Winsted, CT 06098

  174 Wallens St Unit C3, Winsted, CT 06098
• 

  /2

  $39,900

  • 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
• 

  $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 $148,257

  Last Listing Agent Kristen Duchene Litchfield County Real Estate

  9 Loomis St, Winsted, CT 06098
• 

  Est $285,029 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,040 Sq Ft

  17 Colony Dr, Winsted, CT 06098

  17 Colony Dr, 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
• 

  $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 $285,729 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  159 Pratt St, Winsted, CT 06098

  159 Pratt St, Winsted, CT 06098
• 

  

  /25

  $184,900 Pending

  • 3 Beds
  • 1 Bath
  • 980 Sq Ft

  99 Norfolk Rd, Winsted, CT 06098

  Opportunity awaits at this charming 3-bedroom Cape set on 1.3 acres in a peaceful country setting. Nicely perched high and set back from the road, this home offers privacy, curb appeal, and plenty of potential. With vinyl siding, replacement windows, a newer septic, and a classic layout, the bones are here - now bring your ideas and make it shine! Perfect for contractors, investors, or handy

  Lisa McCarthy Coldwell Banker Realty

  99 Norfolk Rd, 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

  Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

  17 Adams St, Winsted, CT 06098
• 

  Est $219,513 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
• 

  /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
• 

  $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 $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
• 

  

  /23

  $230,000

  • 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
• 

  $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 $276,390

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

  325 E Wakefield Blvd, Winsted, CT 06098
• 

  Est $265,327 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
• 

  

  /13

  $649,900

  • 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
• 

  $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 $275,564 Not Listed For Sale

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

  160 Glendale Ave, Winsted, CT 06098

  160 Glendale Ave, Winsted, CT 06098
• 

  

  /24

  $365,000

  • 3 Beds
  • 2.5 Baths
  • 2,356 Sq Ft

  95 Nalette Dr, Winsted, CT 06098

  Stunning Contemporary Home on a Quiet Corner Lot. This unique home offers a beautifully updated open floor plan that seamlessly blends the kitchen, dining, and living areas-perfect for modern living and entertaining. The kitchen features granite countertops, ample cabinetry, stainless steel appliances, and great flow into the main living space. The first floor includes a refinished half bathroom

  Jennifer Mitchell Northwest CT Realty

  95 Nalette Dr, Winsted, CT 06098
• 

  $190,000 Sold Dec 23, 2024

  14 Pine Rd, Colebrook, CT 06021

  • Land
  • 2.39 Acres
  • $79,498 per Acre

  Last Sold Summary

  • 24% Below List Price
  • 43 Days On Market

  Current Estimated Value $217,604

  Last Listing Agent LAURA BARTLETT Northwest CT Realty

  14 Pine Rd, Colebrook, CT 06021
• 

  Est $314,280 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
• 

  

  /32

  $259,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,444 Sq Ft

  10 Crescent St, Winsted, CT 06098

  A multi-family home close to town with spacious bedrooms and living space. Plenty of storage and parking. Close to all forms of transportation, schools and shopping. Come check it out today!!

  Thomas Mele Dorrance Realty

  10 Crescent St, 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

  Last Listing Agent Jill Menard Realty One Group Cutting Edge

  115 Laurel Way, Winsted, CT 06098
• 

  Est $208,996 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
• 

  

  /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
• 

  $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 $214,978 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

Showing Results 81 - 120, Page 3 of 18