Winsted, CT Homes

• 

  Est $308,332 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
• 

  

  

  /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
• 

  $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 $273,643 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

  $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
• 

  $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 $206,741 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
• 

  

  /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
• 

  $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 $350,002 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,608 Sq Ft

  155 West Rd, Winsted, CT 06098

  155 West Rd, 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
• 

  $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 $417,148 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
• 

  

  /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
• 

  $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 $295,680 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
• 

  

  /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
• 

  $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 $348,715 Not Listed For Sale

  • 5 Beds
  • 2,820 Sq Ft

  204 Gilbert Ave, Winsted, CT 06098

  204 Gilbert Ave, Winsted, CT 06098
• 

  

  /32

  $225,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,051 Sq Ft

  817 E Wakefield Blvd, Winsted, CT 06098

  Perched atop a scenic hill overlooking picturesque Highland Lake, this charming ranch offers 1,051+/- square feet of inviting living space with two bedrooms and two full bathrooms. The galley-style kitchen features Thomasville cabinetry and Corian countertops, opening to an intimate dining room with tranquil lake views. Take your pick of relaxing spaces-whether it's the cozy living room with an

  George Sznaj DB Associates of CT, LLC

  817 E Wakefield Blvd, 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 $245,189 Not Listed For Sale

  • 6 Beds
  • 2,421 Sq Ft

  3 Brookside Ave, Winsted, CT 06098

  3 Brookside Ave, Winsted, CT 06098
• 

  

  /11

  $159,000

  • 2 Beds
  • 1.5 Baths
  • 832 Sq Ft

  8 Oak St, Winsted, CT 06098

  Discover a low maintenance and hassle-free alternative to condo living with this easy-to-maintain, single-family home , perfect for investors, first-time buyers, or anyone seeking simplified living without the burden of HOA fees. Step inside to an efficient layout featuring brand-new WREN kitchen cabinets, granite countertops, a new gas stove, and a new refrigerator, offering a fresh and modern

  Austin Brochu Sullivan Real Estate Inc

  8 Oak St, Winsted, CT 06098
• 

  $370,000 Sold Dec 20, 2024

  129 Skinner Rd, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 2,177 Sq Ft
  • Built 1978

  Last Sold Summary

  • $170/SF
  • 34 Days On Market

  Current Estimated Value $396,905

  Last Listing Agent Christopher Gueniat Northwest CT Realty

  129 Skinner Rd, Winsted, CT 06098
• 

  Est $211,833 Not Listed For Sale

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

  111 Riverton Rd Unit 66, Winsted, CT 06098

  111 Riverton Rd Unit 66, Winsted, CT 06098
• 

  

  /5

  $295,000

  • Land
  • 51 Acres
  • $5,784 per Acre

  393 Winchester Rd, Winsted, CT 06098

  WINCHESTER CREST 51 acres of forested gently rolling land sited upland in Winchester Center. There is a former homesite and multiple choices for additional homesites affording complete privacy. There is abundant wildlife, trails, intermittent streams, dense and sparse forest. Perfect for year round home site, weekend retreat or recreational land.

  Tom McGowan Elyse Harney Real Estate

  393 Winchester Rd, 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 $258,618 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,076 Sq Ft

  45 Beach St, Winsted, CT 06098

  45 Beach St, Winsted, CT 06098
• 

  

  /39

  $920,000

  • 4 Beds
  • 2 Baths
  • 3,088 Sq Ft

  469 Platt Hill Rd, Winsted, CT 06098

  HOME-LAND -BARN. A TRUE NEW ENGLAND CLASSIC PROPERTY IN A POST CARD SETTING! For the Discerning Customer, whether You're an ANTIQUARIAN, HORSE & ANIMAL LOVER, or just seeking for a PEACEFUL & TRANQUIL LOCATION, this LITCHFIELD COUNTY HOME could possibly fit your Criteria. Stately 1789 11 Room 3,088 Sq. Ft. Colonial expresses Love, Warmth & Care. From the Solid Beams, Chestnut Wide-Board Floors,

  Marshall Cohen Cohen Agency

  469 Platt Hill 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 $445,180 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,313 Sq Ft

  193 Spencer Hill Rd, Winsted, CT 06098

  193 Spencer Hill Rd, Winsted, CT 06098
• 

  

  /35

  $419,000 Under Contract

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

  117 South Rd, Winsted, CT 06098

  Nestled in a peaceful rural setting of Winchester Center, this charming home offers a perfect blend of rustic character and modern convenience. The property is located on over 3.3 acres of land and is adjacent to a scenic pond. Inside you will find a three bedroom two bath home with an additional in law apartment with one full bath and one bedroom and its own private entrance. The home also

  Christina Niziolek William Raveis Real Estate

  117 South Rd, 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 $347,139 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,379 Sq Ft

  160 Hinsdale Ave, Winsted, CT 06098

  160 Hinsdale Ave, Winsted, CT 06098
• 

  

  /12

  $750,000

  • 4 Beds
  • 2 Baths
  • 5,389 Sq Ft

  436 Main St, Winsted, CT 06098

  One-of-a-Kind opportunity with 4 apartments plus a turnkey, award-winning restaurant in the heart of Litchfield County, perfectly situated in a high-traffic location. The well-established business offers 2,177 sq. ft. of warm, inviting atmosphere with 65 indoor seats and 35 outdoor seats-ideal for both casual dining and special occasions. Has a cafe license (liquor) but no bar. With a 10-year

  Tony Goia The Washington Agency

  436 Main St, Winsted, 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 $248,180 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft

  234 Oak St, Winsted, CT 06098

  234 Oak St, Winsted, CT 06098
• 

  

  /35

  $849,900

  • 4 Beds
  • 2 Baths
  • 1,781 Sq Ft

  119 W Wakefield Blvd, Winsted, CT 06098

  Have you been dreaming of breathtaking lake views and a property that is truly special, unique, and turn-key? This exceptional home includes 50 feet of waterfront access with a boat dock and lift, making it a dream for lake enthusiasts! Nestled across from the tranquil First Bay, this beautifully renovated two-family home can be enjoyed as a single-family retreat or an income-generating

  Mela Veltri Case KW Legacy Partners

  119 W Wakefield Blvd, Winsted, 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 $153,449

  Last Listing Agent Jeffrey Liskin Northwest CT Realty

  234 E Wakefield Blvd, Winsted, CT 06098
• 

  Est $202,034 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 734 Sq Ft

  110 E Mountain Ave, Winsted, CT 06098

  110 E Mountain Ave, Winsted, CT 06098

Showing Results 81 - 120, Page 3 of 18