Winsted, CT Homes

• 

  

  

  /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
• 

  $45,000 Sold May 09, 2025

  269 Walnut St, Winsted, CT 06098

  • Land
  • 0.5 Acre
  • $90,000 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 72 Days On Market

  Last Listing Agent David Sartirana Northwest CT Realty

  269 Walnut St, Winsted, CT 06098
• 

  Est $198,876 Not Listed For Sale

  111 Riverton Rd Unit 30, Winsted, CT 06098

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

  111 Riverton Rd Unit 30, Winsted, CT 06098

  Last Sold Summary

  • 14% Above List Price
  • $145/SF
  • 0 Days On Market

  Last Sold Price $175,000

  Last Listing Agent Patricia Scarpa Marino Realty LLC
• 

  

  

  /38

  $289,000 Under Contract

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

  174 Wallens St Unit A5, Winsted, CT 06098

  Welcome to Clockmakers Hill, a desirable and active 55+ community offering comfort, convenience, and vibrant living. This immaculately maintained 2 bedroom, 2.5 bath condo blends thoughtful updates with everyday functionality. Warm wood flooring enhances the main living areas, while the kitchen features tile flooring, granite countertops, stainless steel appliances, and a pantry customized with

  Lauren Iraeta KW Legacy Partners

  174 Wallens St Unit A5, Winsted, CT 06098
• 

  $1,575,000 Sold Jun 30, 2025

  508 W Wakefield Blvd, Winsted, CT 06098

  • 7 Beds
  • 4 Baths
  • 2,687 Sq Ft
  • Built 1890

  Last Sold Summary

  • 5% Below List Price
  • $586/SF
  • 316 Days On Market

  Current Estimated Value $1,622,303

  Last Listing Agent Pierre Moran William Pitt Sotheby's Int'l

  508 W Wakefield Blvd, Winsted, CT 06098
• 

  Est $298,313 Not Listed For Sale

  182 Florence St, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,982 Sq Ft
  • Built 1979

  182 Florence St, Winsted, CT 06098

  Last Sold Summary

  • 2% Above List Price
  • $148/SF
  • 40 Days On Market

  Last Sold Price $293,000

  Last Listing Agent Heidi Picard-Ramsay Berkshire Hathaway Home Services
• 

  

  /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
• 

  $360,000 Sold Feb 25, 2026

  187 Torringford St, Winsted, CT 06098

  • 4 Beds
  • 1.5 Baths
  • 2,365 Sq Ft
  • Built 1800

  Last Sold Summary

  • 16% Below List Price
  • $152/SF
  • 109 Days On Market

  Current Estimated Value $396,977

  Last Listing Agent Jessica Washington William Raveis Real Estate

  187 Torringford St, Winsted, CT 06098
• 

  Est $260,972 Not Listed For Sale

  36 Charles St, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,180 Sq Ft
  • Built 1957

  36 Charles St, Winsted, CT 06098

  Last Sold Summary

  • 9% Above List Price
  • $203/SF
  • 5 Days On Market

  Last Sold Price $240,000

  Last Listing Agent Judy Guarco Berkshire Hathaway Home Services
• 

  

  /26

  $230,000 Under Contract

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

  9 John St, Winsted, CT 06098

  Fully renovated 1870 Colonial offering 1,172 sq. ft. of thoughtfully updated living space that blends historic character with modern comfort. Hardwood floors run through the living room and both bedrooms, creating a warm and inviting feel. The flexible layout includes a convenient first-floor bedroom and a spacious primary bedroom on the second level. The bright, refreshed kitchen features new

  Michael Grady William Raveis Real Estate

  9 John St, Winsted, CT 06098
• 

  $151,000 Sold Feb 20, 2026

  155 Rockwell St, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,317 Sq Ft
  • Built 1953

  Last Sold Summary

  • 5% Below List Price
  • $115/SF
  • 11 Days On Market

  Current Estimated Value $251,338

  Last Listing Agent Joseph Caslin Sailpoint Property Group

  155 Rockwell St, Winsted, CT 06098
• 

  Est $363,900 Not Listed For Sale

  133 E Wakefield Blvd, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,594 Sq Ft
  • Built 1962

  133 E Wakefield Blvd, Winsted, CT 06098

  Last Sold Summary

  • 17% Above List Price
  • $194/SF
  • 26 Days On Market

  Last Sold Price $310,000

  Last Listing Agent David Sartirana Northwest CT Realty
• 

  

  /29

  $285,000 Pending

  • 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. View the property during open houses only Saturday 2/2/26 and Sunday 2/8/26 from

  Raelyn Lawrence Coldwell Banker Realty

  95 Colony Dr, Winsted, CT 06098
• 

  $279,900 Sold Sep 12, 2025

  39 Colony Dr, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,183 Sq Ft
  • Built 1969

  Last Sold Summary

  • $237/SF
  • 65 Days On Market

  Current Estimated Value $287,615

  Last Listing Agent Alison Behlman Tier 1 Real Estate

  39 Colony Dr, Winsted, CT 06098
• 

  Est $275,216 Not Listed For Sale

  257 Walnut St, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,490 Sq Ft
  • Built 1900

  257 Walnut St, Winsted, CT 06098

  Last Sold Summary

  • 11% Above List Price
  • $167/SF
  • 21 Days On Market

  Last Sold Price $249,000

  Last Listing Agent Meagan Albert Tier 1 Real Estate
• 

  

  /27

  $375,000 Pending

  • 3 Beds
  • 3,660 Sq Ft

  57 Main St, Winsted, CT 06098

  Wonderful multiuse property on Main St. in Winsted. Currently used as a cleaners on the first floor and residential unit on the second floor. Multiple possibilities for this building which is in a prime location. Potential to take over the current business and rent or live in second floor, covert to multifamily or start a new business venture. This property is also listed as commercial with MLS

  Stacy LaQuerre Regall Realty, LLC

  57 Main St, Winsted, CT 06098
• 

  $279,000 Sold May 19, 2025

  56 Lakeview Rd, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,101 Sq Ft
  • Built 1956

  Last Sold Summary

  • 16% Above List Price
  • $253/SF
  • 6 Days On Market

  Current Estimated Value $242,938

  Last Listing Agent Tony Goia The Washington Agency

  56 Lakeview Rd, Winsted, CT 06098
• 

  Est $301,015 Not Listed For Sale

  204 Gilbert Ave, Winsted, CT 06098

  • 5 Beds
  • 2,820 Sq Ft
  • Built 1875

  204 Gilbert Ave, Winsted, CT 06098

  Last Sold Summary

  • 9% Above List Price
  • $98/SF
  • 10 Days On Market

  Last Sold Price $275,000

  Last Listing Agent Austin Brochu Sullivan Real Estate Inc
• 

  

  /31

  $269,999 Pending

  • 3 Beds
  • 2 Baths
  • 1,652 Sq Ft

  118 Meadow St, Winsted, CT 06098

  This charming historic home, built in 1860, blends timeless character with thoughtful updates. Featuring 3-4 bedrooms, this property offers flexible living space to meet your needs. The beautifully remodeled upstairs bathroom is a standout feature, offering modern comfort within this classic home. Enjoy your LARGE eat-in kitchen with laundry hook ups and plenty of natural lighting and ample

  Ashley Henry The Washington Agency

  118 Meadow 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 $719,621

  Last Listing Agent Matthew Egan Regency Real Estate, LLC

  110 South Rd, Winsted, CT 06098
• 

  Est $203,313 Not Listed For Sale

  111 Riverton Rd Unit 53, Winsted, CT 06098

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

  111 Riverton Rd Unit 53, Winsted, CT 06098

  Last Sold Summary

  • 2% Above List Price
  • $165/SF
  • 12 Days On Market

  Last Sold Price $199,000

  Last Listing Agent Samantha Behm William Pitt
• 

  

  /23

  $274,900 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,267 Sq Ft

  9 Central Ave, Winsted, CT 06098

  Welcome to this adorable, solidly built Cape in the heart of Winchester, Connecticut-where home is more than just a place, it's a way of life. Nestled in the scenic Litchfield Hills, Winchester is a community full of character, rich history, and strong local businesses, offering a wonderful quality of life. From excellent schools and charming downtown shops to beautiful lakes and outdoor

  Suzie Larson Turning Point Realty, LLC

  9 Central Ave, 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 $304,666

  Last Listing Agent Antonio De La Cruz Eagle Eye Realty PLLC

  62 Fruit St Unit 64, Winsted, CT 06098
• 

  Est $232,952 Not Listed For Sale

  3 Brookside Ave, Winsted, CT 06098

  • 6 Beds
  • 2,421 Sq Ft
  • Built 1900

  3 Brookside Ave, Winsted, CT 06098

  Last Sold Summary

  • 37% Above List Price
  • $70/SF
  • 78 Days On Market

  Last Sold Price $170,000

  Last Listing Agent Jayson Kemp Five Stars Realty
• 

  

  /36

  $1,850,000

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

  431 W Wakefield Blvd, Winsted, CT 06098

  Live the Highland Lake Dream - 431 W. Wakefield Blvd, Winchester, CT Summer is just around the corner - and in Winsted, resort living never ends. Recently named one of the most desirable towns to live in, with the breathtaking Highland Lake at its heart, Winchester offers the perfect blend of beauty and lifestyle. This waterfront estate at 431 W. Wakefield Blvd isn't just a home - it's your

  Lisa Ogren Berkshire Hathaway NE Prop.

  431 W Wakefield Blvd, 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 $382,100

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

  226 E Wakefield Blvd, Winsted, CT 06098
• 

  Est $198,847 Not Listed For Sale

  111 Riverton Rd Unit 66, Winsted, CT 06098

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

  111 Riverton Rd Unit 66, Winsted, CT 06098

  Last Sold Summary

  • 11% Above List Price
  • $149/SF
  • 0 Days On Market

  Last Sold Price $179,900

  Last Listing Agent Amy Sartirana Northwest CT Realty
• 

  $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 $140,795

  Last Listing Agent James Bradshaw Berkshire Hathaway NE Prop.

  13 Riveredge Dr Unit 13, Winsted, CT 06098
• 

  Est $251,270 Not Listed For Sale

  45 Beach St, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 2,076 Sq Ft
  • Built 1900

  45 Beach St, Winsted, CT 06098

  Last Sold Summary

  • 56% Above List Price
  • $78/SF
  • 97 Days On Market

  Last Sold Price $161,500

  Last Listing Agent Michael Barnes Coldwell Banker Realty
• 

  $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 $261,927

  Last Listing Agent Patrick Precourt Meridian Realty Group LLC

  343 W Wakefield Blvd, Winsted, CT 06098
• 

  Est $421,983 Not Listed For Sale

  193 Spencer Hill Rd, Winsted, CT 06098

  • 4 Beds
  • 2.5 Baths
  • 2,313 Sq Ft
  • Built 2012

  193 Spencer Hill Rd, Winsted, CT 06098

  Last Sold Summary

  • 46% Above List Price
  • $125/SF
  • 57 Days On Market

  Last Sold Price $290,000

  Last Listing Agent Victor Santana Santana Realty Group LLC
• 

  $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 $151,214

  Last Listing Agent Kristen Duchene Litchfield County Real Estate

  9 Loomis St, Winsted, CT 06098
• 

  Est $344,333 Not Listed For Sale

  160 Hinsdale Ave, Winsted, CT 06098

  • 4 Beds
  • 1.5 Baths
  • 2,379 Sq Ft
  • Built 1930

  160 Hinsdale Ave, Winsted, CT 06098

  Last Sold Summary

  • 2% Below List Price
  • $147/SF
  • 46 Days On Market

  Last Sold Price $350,000

  Last Listing Agent Laura Krzewski Realtor Bolanos & Associates LLC
• 

  $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 $251,790 Not Listed For Sale

  234 Oak St, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft
  • Built 1890

  234 Oak St, Winsted, CT 06098

  Last Sold Summary

  • 7% Above List Price
  • $180/SF
  • 29 Days On Market

  Last Sold Price $235,000

  Last Listing Agent Timothy McGrane Berkshire Hathaway Home Services
• 

  $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 $314,065

  Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

  17 Adams St, Winsted, CT 06098
• 

  Est $199,633 Not Listed For Sale

  110 E Mountain Ave, Winsted, CT 06098

  • 2 Beds
  • 1 Bath
  • 734 Sq Ft
  • Built 1945

  110 E Mountain Ave, Winsted, CT 06098

  Last Sold Summary

  • 60% Above List Price
  • $170/SF
  • 36 Days On Market

  Last Sold Price $125,000

  Last Listing Agent David D'Amore Northwest CT Realty
• 

  $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 $266,094 Not Listed For Sale

  24 Union St, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 2,582 Sq Ft
  • Built 1895

  24 Union St, Winsted, CT 06098

  Last Sold Summary

  • 6% Above List Price
  • $97/SF
  • 47 Days On Market

  Last Sold Price $250,000

  Last Listing Agent Farzaneh RE/MAX
• 

  $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 $286,927

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

  325 E Wakefield Blvd, Winsted, CT 06098

Showing Results 81 - 120, Page 3 of 18