Winsted, CT Homes

• 

  $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 $305,515

  Last Listing Agent Antonio De La Cruz Eagle Eye Realty PLLC

  62 Fruit St Unit 64, Winsted, CT 06098
• 

  Est $265,804

  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

  • 5 Days On Market

  Last Listing Agent Judy Guarco Berkshire Hathaway NE Prop.
• 

  

  

  /6

  $386,000

  • Land
  • 1.91 Acres
  • $202,094 per Acre

  00 Main St, Winsted, CT 06098

  Exceptional 2+ Acre Development Opportunity - Route 44, Winsted, CT** Rare opportunity to acquire approximately 2+- acres with nearly 700 feet of frontage on Main Street (Route 44), one of Winsted's primary commercial corridors. Located within the Town Gateway Zone, this highly visible parcel offers outstanding flexibility for a variety of development opportunities, including commercial,

  Dan Merrigan Merrigan & Lefebvre Realty

  00 Main 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 $403,719

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

  226 E Wakefield Blvd, Winsted, CT 06098
• 

  Est $387,081

  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

  • 26 Days On Market

  Last Listing Agent David Sartirana Northwest CT Realty
• 

  

  /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
• 

  $475,000

  Sold Jul 10, 2026

  5 Stadler Heights, Winsted, CT 06098

  • 4 Beds
  • 2.5 Baths
  • 3,556 Sq Ft
  • Built 1990

  Last Sold Summary

  • 5% Below List Price
  • $134/SF
  • 118 Days On Market

  Current Estimated Value $502,951

  Last Listing Agent David Sartirana Northwest CT Realty

  5 Stadler Heights, Winsted, CT 06098
• 

  Est $293,944

  Not Listed For Sale

  14 Hamill Dr, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,888 Sq Ft
  • Built 1973

  14 Hamill Dr, Winsted, CT 06098

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Eva Casoria eXp Realty
• 

  

  /36

  $353,500

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,324 Sq Ft

  195 Reaching Hill Rd, Winsted, CT 06098

  Please submit your client's highest and best offer by Sunday 07/19 at 3:00 PM. Beautifully remodeled and move-in ready, 195 Reaching Hill Rd in Winsted, CT features modern updates, comfort, and functionality throughout. This 3-bedroom, 2-bath conventional-style home sits on nearly one acre of land and showcases a bright open-concept layout with beautiful hardwood floors, a spacious living area,

  Nicolle Estrella eXp Realty

  195 Reaching Hill Rd, Winsted, CT 06098
• 

  $270,000

  Sold Aug 06, 2026

  104 Maloney Ct, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Built 1957

  Last Sold Summary

  • 7% Below List Price
  • $268/SF
  • 67 Days On Market

  Current Estimated Value $276,918

  Last Listing Agent Lisa Garten Johnson Turning Point Realty, LLC

  104 Maloney Ct, Winsted, CT 06098
• 

  Est $279,074

  Not Listed For Sale

  830 Main St, Winsted, CT 06098

  • 5 Beds
  • 4 Baths
  • 3,115 Sq Ft
  • Built 1900

  830 Main St, Winsted, CT 06098

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate
• 

  

  /40

  $600,000

  Open Sun 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 3,486 Sq Ft

  205 Wallens St, Winsted, CT 06098

  Welcome to this beautifully crafted 3,486 sq. ft. Colonial, offering exceptional quality, thoughtful design, and plenty of space both inside and out. Set privately on 2.03 acres at the end of a long driveway, this 10-room home was built in 2007 and has been meticulously maintained. The main level features gleaming hardwood floors, a spacious family room with fireplace, and an incredible gourmet

  Kelly Sullivan Sullivan Real Estate Inc

  205 Wallens 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 $273,167

  Last Listing Agent Patrick Precourt Century 21 Clemens Group

  343 W Wakefield Blvd, Winsted, CT 06098
• 

  Est $289,750

  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

  • 21 Days On Market

  Last Listing Agent Meagan Albert Tier 1 Real Estate
• 

  

  /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
• 

  $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 $210,240

  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

  • 12 Days On Market

  Last Listing Agent Samantha Behm William Pitt Sotheby's Int'l
• 

  

  /40

  $895,000

  • 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
• 

  $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 $317,267

  Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

  17 Adams St, Winsted, CT 06098
• 

  Est $204,559

  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

  • 0 Days On Market

  Last Listing Agent Amy Sartirana Northwest CT Realty
• 

  

  /24

  $124,900

  $75K PRICE DROP Under Contract

  • Land
  • 5,227 Sq Ft
  • $1,040,833 per Acre

  624 Wynne Rd, Winsted, CT 06098

  Exceptional opportunity to build near one of Northwest Connecticut's most desirable lake communities. Just steps from beautiful Highland Lake, this water-view parcel offers the chance to create your dream home in a setting that combines lake lifestyle, natural beauty, and convenient access to some of Litchfield County's most sought-after destinations. Highland Lake is a true Connecticut gem-a

  AJ Davis Better Homes and Gardens Real Estate Executive Real Estate

  624 Wynne Rd, Winsted, CT 06098
• 

  $550,000

  Sold Jul 01, 2026

  257 Wallens Hill Rd, Winsted, CT 06098

  • 3 Beds
  • 2.5 Baths
  • 2,011 Sq Ft
  • Built 1955

  Last Sold Summary

  • 2% Above List Price
  • $273/SF
  • 30 Days On Market

  Current Estimated Value $529,816

  Last Listing Agent Kelly Sullivan Sullivan Real Estate Inc

  257 Wallens Hill Rd, Winsted, CT 06098
• 

  Est $247,408

  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

  • 97 Days On Market

  Last Listing Agent Michael Barnes Coldwell Banker Realty
• 

  

  /26

  $239,000

  • 7 Beds
  • 3 Baths
  • 2,400 Sq Ft

  Unlisted Address

  Brand new to the market. Must see large 2 story Colonial featuring 13 rooms, 7 Bedrooms, 3 Bathrooms, Walk up attic and full basement. Includes a 2 story barn. Convenient location in the heart of town lends itself to easy access to many nearby amenities. As an investment this residence also has great potential to convert to a multi family home or could be renovated for commercial office space.

  Frank J. Berg Broker/Owner Town & Country Real Estate

  Unlisted Address
• 

  $1,475,000

  Sold Jun 09, 2026

  129 E Lake St, Winsted, CT 06098

  • 3 Beds
  • 3.5 Baths
  • 2,699 Sq Ft
  • Built 1910

  Last Sold Summary

  • 1% Below List Price
  • $546/SF
  • 12 Days On Market

  Current Estimated Value $1,423,524

  Last Listing Agent KAREN NEWTON William Pitt Sotheby's Int'l

  129 E Lake St, Winsted, CT 06098
• 

  Est $413,609

  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

  • 57 Days On Market

  Last Listing Agent Victor Santana Santana Realty Group LLC
• 

  

  /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
• 

  $325,000

  Sold Jun 10, 2026

  90 Colony Dr, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,282 Sq Ft
  • Built 1969

  Last Sold Summary

  • 7% Below List Price
  • $254/SF
  • 64 Days On Market

  Current Estimated Value $327,086

  Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

  90 Colony Dr, Winsted, CT 06098
• 

  Est $345,102

  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

  • 46 Days On Market

  Last Listing Agent Laura Krzewski Realtor Bolanos & Associates LLC
• 

  

  /24

  $395,000

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

  720 Main St, Winsted, CT 06098

  Where Opportunity Meets Lifestyle! Unlock the potential of this exceptional mixed-use property located in the heart of downtown Winsted. Positioned on a bustling Main Street with excellent exposure and constant pedestrian traffic, this property is an outstanding opportunity for entrepreneurs, investors, or anyone looking to combine business ownership with residential living. The street-level

  Arlene Gonzalez The Gonzalez Property Group

  720 Main St, 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

  Current Estimated Value $262,084

  Last Listing Agent Terence Dominick Exceptional Real Estate LLC

  22 Curtice St, Winsted, CT 06098
• 

  Est $283,190

  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

  • 29 Days On Market

  Last Listing Agent Timothy McGrane Berkshire Hathaway NE Prop.
• 

  

  /31

  $259,000

  $31K PRICE DROP

  • 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
• 

  $387,500

  Sold Jul 21, 2026

  68 Wetmore Ave, Winsted, CT 06098

  • 6 Beds
  • 2.5 Baths
  • 2,555 Sq Ft
  • Built 1900

  Last Sold Summary

  • 11% Above List Price
  • $152/SF
  • 60 Days On Market

  Current Estimated Value $308,864

  Last Listing Agent Alex King Lock and Key Realty, Inc

  68 Wetmore Ave, Winsted, CT 06098
• 

  Est $356,826

  Not Listed For Sale

  284 Gilbert Ave, Winsted, CT 06098

  • 4 Beds
  • 1 Bath
  • 1,849 Sq Ft
  • Built 1956

  284 Gilbert Ave, Winsted, CT 06098

  Last Sold Summary

  • 40 Days On Market

  Last Listing Agent David Sartirana Northwest CT Realty
• 

  

  /29

  $269,900

  $30K PRICE DROP Under Contract

  • 2 Beds
  • 1 Bath
  • 702 Sq Ft

  147 E Wakefield Blvd, Winsted, CT 06098

  Come enjoy Highland Lake living just in time for Summer. Relax in this one level living, cozy cottage home with views of the lake from your deck and just a short distance to Resha beach. Enter through a large mudroom to your open living room with large window to let in natural light, updated kitchen, 2 bedrooms, 1 full bath, main level laundry, front and rear deck, large yard & shed. New flooring

  Mary Mary LeBlanc Realty

  147 E Wakefield Blvd, Winsted, CT 06098
• 

  $204,000

  Sold Jun 15, 2026

  111 Torringford St Unit 33, Winsted, CT 06098

  • 2 Beds
  • 2 Baths
  • 1,102 Sq Ft
  • Built 1987

  Last Sold Summary

  • 7% Above List Price
  • $185/SF
  • 32 Days On Market

  Current Estimated Value $199,820

  Last Listing Agent Ryan Horvay Smith & DeGroat Real Estate

  111 Torringford St Unit 33, Winsted, CT 06098
• 

  Est $296,565

  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

  • 47 Days On Market

  Last Listing Agent Farzaneh RE/MAX Alliance
• 

  

  /37

  $1,850,000

  Pending

  • 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
• 

  $335,000

  Sold Jul 10, 2026

  405 N Main St, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,466 Sq Ft
  • Built 1890

  Last Sold Summary

  • 4% Below List Price
  • $229/SF
  • 4 Days On Market

  Current Estimated Value $340,615

  Last Listing Agent Nancy Reardon Berkshire Hathaway NE Prop.

  405 N Main St, Winsted, CT 06098

Showing Results 81 - 120, Page 3 of 18