Winsted, CT Homes

• 

  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
• 

  

  /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
• 

  $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 $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
• 

  

  

  /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
• 

  $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 $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
• 

  

  /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
• 

  $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 $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

  $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
• 

  $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 $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
• 

  

  /12

  $170,000

  • 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
• 

  $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 $245,189 Not Listed For Sale

  • 6 Beds
  • 2,421 Sq Ft

  3 Brookside Ave, Winsted, CT 06098

  3 Brookside Ave, Winsted, CT 06098
• 

  

  /32

  $225,000 Pending

  • 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
• 

  $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 $212,432 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
• 

  

  /11

  $159,000 Pending

  • 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
• 

  $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 $256,551 Not Listed For Sale

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

  45 Beach St, Winsted, CT 06098

  45 Beach St, Winsted, CT 06098
• 

  

  /5

  $295,000 Under Contract

  • 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 $281,721

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

  325 E Wakefield Blvd, Winsted, CT 06098
• 

  Est $415,704 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
• 

  

  /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 $344,204 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
• 

  $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 $250,119 Not Listed For Sale

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

  234 Oak St, Winsted, CT 06098

  234 Oak St, Winsted, CT 06098
• 

  

  /28

  $275,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,971 Sq Ft

  43 Wallens St, Winsted, CT 06098

  Highest and best 1/4/26 by 5pm Welcome to 43 Wallens Street in the heart of Winsted - a versatile two-family property ideal for owner-occupants, investors or an in law. The first-floor unit offers a one-bedroom layout with recessed lighting, while the spacious second unit features three bedrooms, including one on the main level and two on the upper floor, plus an additional room on the main level

  Kristen Duchene Litchfield County Real Estate

  43 Wallens 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 $196,452 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
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  /17

  $295,000

  • 2 Beds
  • 1 Bath
  • 1,218 Sq Ft

  343 E Wakefield Blvd, Winsted, CT 06098

  Cape-style home with 2 bedrooms and 1 bath, offering 1,218 sq ft on a 0.13-acre lot in desirable Litchfield County. The home has been completely gutted and is ready for a full renovation. Great opportunity to create your ideal living space.

  Thomas Mele Dorrance Realty

  343 E 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 $145,365

  Last Listing Agent Jeffrey Liskin Northwest CT Realty

  234 E Wakefield Blvd, Winsted, CT 06098
• 

  Est $304,117 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,582 Sq Ft

  24 Union St, Winsted, CT 06098

  24 Union St, Winsted, CT 06098
• 

  /2

  $285,000 Open Sat 12PM - 2PM

  • 3 Beds
  • 1.5 Baths
  • 1,008 Sq Ft

  95 Colony Dr, Winsted, CT 06098

  Enjoy easy one-level living in this charming 3-bedroom, 2-bath home offering an eat-in kitchen, hardwood floors throughout, a full basement, garage, and a primary bedroom with its own bath. The yard provides great outdoor space for relaxing or entertaining, all just minutes from Winsted Center, Route 8, and Route 44.

  Raelyn Lawrence Coldwell Banker Realty

  95 Colony Dr, Winsted, CT 06098
• 

  $194,900 Sold Dec 08, 2025

  111 Riverton Rd Unit 61, Winsted, CT 06098

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

  Last Sold Summary

  • 5% Below List Price
  • $162/SF
  • 61 Days On Market

  Last Listing Agent Bethany Lydem Stone Crest Realty LLC

  111 Riverton Rd Unit 61, Winsted, CT 06098
• 

  Est $235,284 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 1,334 Sq Ft

  174 Wallens St Unit C7, Winsted, CT 06098

  174 Wallens St Unit C7, Winsted, CT 06098

Showing Results 81 - 120, Page 3 of 18