Winchester, CT Homes

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  /26

  $279,000

  $10K PRICE DROP Under Contract

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  104 Maloney Ct, Winsted, CT 06098

  Perched on desirable Wallens Hill with beautiful western sunset views, this lovingly maintained 3 bed 1957 ranch is full of warmth, charm, and pride of ownership. Bright and sunny throughout, the home offers 1,008 square feet of comfortable living space with hardwood floors, central air conditioning, and an easy-flow layout designed for everyday living. The spacious eat-in kitchen features oak

  Lisa Garten Johnson Turning Point Realty, LLC

  104 Maloney Ct, Winsted, CT 06098
• 

  $320,000

  Sold Jun 26, 2026

  621 Wynne Rd, Winsted, CT 06098

  • 2 Beds
  • 1 Bath
  • 975 Sq Ft
  • Built 1995

  Last Sold Summary

  • 6% Below List Price
  • $328/SF
  • 42 Days On Market

  Current Estimated Value $330,885

  Last Listing Agent David Sartirana Northwest CT Realty

  621 Wynne Rd, Winsted, CT 06098
• 

  Not Listed For Sale

  319 Taylor Brook Rd, Winsted, CT 06098

  • 4 Beds
  • 2.5 Baths
  • 2,969 Sq Ft
  • Built 1990

  319 Taylor Brook Rd, Winsted, CT 06098

  Last Sold Summary

  • 4 Days On Market
• 

  

  

  /25

  $474,900

  $25K PRICE DROP Pending

  • 5 Beds
  • 3 Baths
  • 3,404 Sq Ft

  441 Platt Hill Rd, Winsted, CT 06098

  Tucked away on 2.09 private acres in the desirable Platt Hill area of Winchester, this custom-built contemporary offers the perfect blend of architectural character, space, and recent updates. With over 3,400 square feet, 5 bedrooms, 3 full baths, and a 2-car garage, this home provides flexibility for everyday living, entertaining, or multi-generational needs. Inside, you'll find a thoughtfully

  Meagan Albert Tier 1 Real Estate

  441 Platt Hill Rd, 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 $297,466

  Last Listing Agent Antonio De La Cruz Eagle Eye Realty PLLC

  62 Fruit St Unit 64, Winsted, CT 06098
• 

  Est $284,906

  Not Listed For Sale

  58 Cherry St, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,287 Sq Ft
  • Built 1948

  58 Cherry St, Winsted, CT 06098

  Last Sold Summary

  • 22 Days On Market
• 

  

  /28

  $349,999

  Under Contract

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

  68 Wetmore Ave, Winsted, CT 06098

  Extremely well-cared-for two-family home located on a desirable street! This property offers plenty of off-street parking, a rear lot, a 3-car garage with basement adds potential for additional income. Large back yard with gazebo.The first floor is unoccupied, while the second floor is tenant-occupied, making this a great opportunity for an owner-occupant or investor. Come take a look while it

  Alex King Lock and Key Realty, Inc

  68 Wetmore Ave, 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 $378,003

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

  226 E Wakefield Blvd, Winsted, CT 06098
• 

  Est $269,346

  Not Listed For Sale

  160 Glendale Ave, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,114 Sq Ft
  • Built 1957

  160 Glendale Ave, Winsted, CT 06098

  Last Sold Summary

  • 85 Days On Market
• 

  

  /8

  $389,000

  • Land
  • 20.87 Acres
  • $18,639 per Acre

  7 Stadler Heights, Winsted, CT 06098

  Welcome, You be the first, to come and conquer this land here in Winchester, Connecticut. There are 20.87 acres of virgin land. Come and build, do what you do best, you can have Peace and Privacy!!! There are no sidewalks, no streets that drive through. You are 40 minutes from multiple private schools. 16 minutes from Charlotte Hungerford Hospital. 1 hour from Tweed Airport New Haven. 39 minutes

  Hector Ortiz KW Legacy Partners

  7 Stadler Heights, Winsted, CT 06098
• 

  $320,000

  Sold Feb 17, 2026

  148 Danbury Quarter Rd, Winchester, CT 06098

  • 4 Beds
  • 2 Baths
  • 1,999 Sq Ft
  • Built 1800

  Last Sold Summary

  • 6% Below List Price
  • $160/SF
  • 86 Days On Market

  Current Estimated Value $322,975

  Last Listing Agent Susan MCGHEE The Washington Agency

  148 Danbury Quarter Rd, Winchester, CT 06098
• 

  Est $332,151

  Not Listed For Sale

  153 Mathew Rd, Winsted, CT 06098

  • 2 Beds
  • 1.5 Baths
  • 1,544 Sq Ft
  • Built 1800

  153 Mathew Rd, Winsted, CT 06098

  Last Sold Summary

  • 141 Days On Market
• 

  

  /40

  $349,900

  Pending

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

  405 N Main St, Winsted, CT 06098

  Move right into this absolutely charming Colonial with incredible curb appeal & pride of ownership throughout! Lovingly maintained & impeccably clean, this true dollhouse is set on .31 acres in the scenic, beautiful Litchfield Hills & just minutes to Northwestern Community College, the town green, shopping, restaurants, walking trails, biking, & endless outdoor recreation. From the moment you

  Nancy Reardon Berkshire Hathaway NE Prop.

  405 N Main 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 $262,964

  Last Listing Agent Patrick Precourt Meridian Realty Group LLC

  343 W Wakefield Blvd, Winsted, CT 06098
• 

  Est $198,016

  Not Listed For Sale

  111 Torringford St Unit 19, Winsted, CT 06098

  • 2 Beds
  • 2 Baths
  • 1,626 Sq Ft
  • Built 1987

  111 Torringford St Unit 19, Winsted, CT 06098

  Last Sold Summary

  • 14 Days On Market
• 

  

  /24

  $544,000

  Under Contract

  • 1 Bed
  • 1.5 Baths
  • 1,308 Sq Ft

  736 W Wakefield Blvd, Winsted, CT 06098

  Welcome to "WatersEdge" a Seasonal Cottage perched on a landscaped hillside overlooking Third Bay of beautiful Highland Lake. Views Views Views! Highland is a fully recreational lake. On the main floor of the cottage you will find one bedroom, a bath with shower, a spacious family room with a stone fireplace, and an efficient kitchen with storage. The lower walk-out level can be accessed by the

  Ed Richman Lakefront Living Realty, LLC

  736 W Wakefield Blvd, 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 $192,976

  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

  • 0 Days On Market
• 

  

  /15

  $799,000

  $60K PRICE DROP

  • Land
  • 65.29 Acres
  • $12,238 per Acre

  257-259 Torringford St, Winchester, CT 06098

  Uncover this hidden gem - 65.29 pristine acres of raw land, with natural beauty and endless potential. This picturesque parcel features serene ponds and mature trees. Distant views and incredible sunsets can be enjoyed from the property. Much site work has been done to date. A driveway with a binder course is already in place offering easy access into and throughout the property. Many acres have

  Lisa Toczko Home Valley Realty, LLC

  257-259 Torringford St, Winchester, 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 $310,769

  Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

  17 Adams St, Winsted, CT 06098
• 

  Est $288,347

  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

  • 40 Days On Market
• 

  

  /5

  $158,000

  $3K PRICE INCREASE

  • 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 CONSIDER

  David D'Amore Northwest CT Realty

  843-845 (lots - 10A, E Wakefield Blvd, Winchester, 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 $370,495

  Last Listing Agent Kelly Sullivan Sullivan Real Estate Inc

  257 Wallens Hill Rd, Winsted, CT 06098
• 

  Est $265,257

  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
• 

  

  /17

  $450,000

  Under Contract

  • 8 Beds
  • 4 Baths
  • 2,000 Sq Ft

  71-73 Wheeler St, Winchester, CT 06098

  A positive income even if you live in one of the units. Two 2 family homes(4 units total) on one parcel. Good parking. Large lot. Residential setting. Second floor of back house has a private deck, back yard and woods, yet is convenient to downtown. Highest and best offers must be submitted by 6/12/26 at 12pm.

  Ida Chaplinski The DIY Listing

  71-73 Wheeler St, Winchester, CT 06098
• 

  $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 $1,438,024

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

  129 E Lake St, Winsted, CT 06098
• 

  Est $372,831

  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
• 

  

  /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
• 

  $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 $333,753

  Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

  90 Colony Dr, Winsted, CT 06098
• 

  Est $260,615

  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
• 

  /2

  $795,000

  • Land
  • 10,018 Sq Ft
  • $3,456,522 per Acre

  535,538 W Wakefield Blvd, Winchester, CT 06098

  This waterfront property is ideal for contractors or individuals who want to build a year-round home on Highland Lake's West side. The property is being sold as a package (3 lots have been approved for construction, parking, and a well ). The lots consist of .10 acres across the street from the water and .023 acres on the water.

  chris marino Cohen Agency

  535,538 W Wakefield Blvd, Winchester, 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 $243,963

  Last Listing Agent Terence Dominick Exceptional Real Estate LLC

  22 Curtice St, Winsted, CT 06098
• 

  Est $216,196

  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
• 

  

  /40

  $1,249,900

  Pending

  • 5 Beds
  • 4 Baths
  • 3,584 Sq Ft

  748 Lake Dr, Winsted, CT 06098

  Rare opportunities like this do not come around often on Highland Lake! Located on the east side of 3rd bay, this unique waterfront property offers beautiful views and magnificent sunsets. This unique waterfront layout offers endless opportunities; from a family compound, multi generational living, guest space or a private lake retreat! Enjoy outdoor living on the massive deck, custom dock, and

  Ryan Horvay Smith & DeGroat Real Estate

  748 Lake Dr, 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 $182,963

  Last Listing Agent Ryan Horvay Smith & DeGroat Real Estate

  111 Torringford St Unit 33, Winsted, CT 06098
• 

  Est $288,751

  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
• 

  

  /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
• 

  $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 $254,930

  Last Listing Agent Jill Menard Realty One Group Cutting Edge

  115 Laurel Way, Winsted, CT 06098
• 

  Est $195,527

  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
• 

  

  /26

  $1,080,000

  $120K PRICE DROP

  • 5 Beds
  • 2.5 Baths
  • 3,307 Sq Ft

  77 Deer Hill Rd, Colebrook, CT 06021

  Enchanting Antique Dutch Colonial Estate with Carriage House and Barn. Nestled in a serene and private 51.2-acre haven, this stately home is a harmonious blend of historic charm and modern sophistication. As you traverse the meandering stone walls and explore the mix of sun-kissed meadows and whispering forests, you'll discover a world where time stands still, yet every modern convenience is at

  MICHAEL CONLOGUE William Pitt Sotheby's Int'l

  77 Deer Hill Rd, Colebrook, CT 06021

Showing Results 81 - 120, Page 3 of 18