Winchester, CT Homes

• 

  Est $261,727

  Not Listed For Sale

  159 Pratt St, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • Built 1900

  159 Pratt St, Winsted, CT 06098

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Cindy Breckheimer Forever Homes Real Estate LLC
• 

  

  

  /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
• 

  $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 $325,303

  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

  Last Listing Agent Heidi Picard-Ramsay Berkshire Hathaway NE Prop.
• 

  

  

  /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
• 

  $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 $317,888

  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

  Last Listing Agent David Sartirana Northwest CT Realty
• 

  

  /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
• 

  $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 $293,391

  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

  Last Listing Agent Cathy Macias Northwest CT Realty
• 

  

  /39

  $749,900

  Pending

  • 2 Beds
  • 1 Bath
  • 760 Sq Ft

  812 W Wakefield Blvd, Winsted, CT 06098

  Year-round waterfront retreat with breathtaking sunrise views from one of the widest sections of the lake! This well-maintained 2-bedroom, 1 bath home offers comfortable living with a flexible loft area for additional sleeping space and a convenient half bath on the lake level. The updated kitchen and new windows provide modern comfort while showcasing expansive water views throughout the home.

  Ryan Horvay Smith & DeGroat Real Estate

  812 W Wakefield Blvd, 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 $346,673

  Last Listing Agent Susan MCGHEE The Washington Agency

  148 Danbury Quarter Rd, Winchester, CT 06098
• 

  Est $329,812

  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

  Last Listing Agent Liz Zakrzewski Coldwell Banker Realty
• 

  

  /23

  $199,900

  • 4 Beds
  • 2 Baths
  • 1,376 Sq Ft

  46 Cherry St, Winsted, CT 06098

  A wonderful opportunity to own a spacious antique Colonial with endless potential! This 4-bedroom, 2-full-bath home features a living room, dining room, and an eat-in kitchen, providing a solid foundation for your vision. While the home would benefit from updates, it offers an excellent opportunity for buyers to add their personal style and transform it into a truly standout property. Ideally

  Debra Jablonski Berkshire Hathaway NE Prop.

  46 Cherry St, 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 $203,347

  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

  Last Listing Agent David Sartirana Northwest CT Realty
• 

  

  /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
• 

  $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 $203,008

  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

  Last Listing Agent Patricia Scarpa Marino Realty LLC
• 

  /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
• 

  $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 $330,579

  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

  Last Listing Agent Heidi Picard-Ramsay Berkshire Hathaway NE Prop.
• 

  

  /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
• 

  $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 $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.
• 

  

  /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
• 

  $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 $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
• 

  

  /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
• 

  $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 $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
• 

  

  /21

  $879,990

  • Land
  • 131.5 Acres
  • $6,692 per Acre

  000000 Norfolk Rd, Winchester, CT 06098

  Rare Multi-Parcel Land Opportunity 5 Contiguous Parcels | Colebrook & Winchester, CT Discover an exceptional land offering spanning five contiguous parcels across two of Litchfield County's most desirable rural towns. This unique property features a strong presence in highly sought-after Colebrook, known for its scenic beauty, low-density living, and unspoiled New England charm-paired with the

  John Harney William Pitt Sotheby's Int'l

  000000 Norfolk Rd, 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 $1,423,524

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

  129 E Lake St, 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
• 

  $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 $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
• 

  $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 $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

Showing Results 81 - 120, Page 3 of 18