Winsted, CT Homes

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  $299,000

  Under Contract

  • 4 Beds
  • 2 Baths
  • 2,270 Sq Ft

  64 Wheeler St, Winsted, CT 06098

  Excellent opportunity for investors! This well-maintained Victorian-style two-family home offers the perfect blend of character, functionality, and income potential. Each spacious unit features 5 rooms, 2 bedrooms, and 1 full bath, with beautiful hardwood flooring throughout and separate, efficient natural gas heating systems. The upper-level apartment also includes a charming enclosed porch,

  

  David Sartirana

  Northwest CT Realty

  64 Wheeler St, Winsted, CT 06098
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  /17

  $1,225 Per Month

  • 2 Beds
  • 1 Bath
  • 756 Sq Ft
  • Apartment for Rent

  111 Rockwell St Unit 1, Winsted, CT 06098

  Rustic charm meets modern convenience in this beautifully updated first floor 2 bedroom, 1 bath apartment located in a well maintained building on a corner lot just minutes from scenic Highland Lake. The spacious layout features a stylish kitchen with granite countertops, stainless steel appliances, and a center island that opens to both covered front and back porches, creating a great space for

  Mike Gregor Cohen Agency SiM, LLC

  111 Rockwell St Unit 1, Winsted, CT 06098
• 

  $300,000

  Sold May 11, 2026

  230 E Wakefield Blvd, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • Built 1978

  Last Sold Summary

  • 6% Below List Price
  • $195/SF
  • 109 Days On Market

  Current Estimated Value $301,082

  Last Listing Agent Peter D'Addeo Commercial Services Realty

  230 E Wakefield Blvd, Winsted, CT 06098
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  Not Listed For Sale

  174 Wallens St Unit D2, Winsted, CT 06098

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft
  • Built 2005

  174 Wallens St Unit D2, Winsted, CT 06098

  Last Sold Summary

  • 39 Days On Market

  Last Listing Agent Ashley Church Turning Point Realty, LLC
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  /38

  $324,900

  • 4 Beds
  • 2 Baths
  • 3,044 Sq Ft

  50 High St, Winsted, CT 06098

  Well-maintained two-family home offering spacious apartments, separate utilities, and a convenient location within walking distance to downtown amenities. The first-floor apartment features approximately 1,620 sq. ft. with a kitchen, living room, dining room, full bath, and 2-3 bedrooms. The second-floor apartment offers approximately 1,424 sq. ft. with a similar layout including a kitchen,

  

  David Sartirana

  Northwest CT Realty

  50 High St, Winsted, CT 06098
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  /22

  $2,100 Per Month

  • 3 Beds
  • 1 Bath
  • 1,042 Sq Ft
  • House for Rent

  34 Rock St, Winsted, CT 06098

  Lovely Colonial home for rent recently remodeled, with large sun filled open concept living room, and separate dining area off of the beautiful fully equipped kitchen. Spacious carpeted mud room with ample room for coats, boots, and backpacks. Wood floors throughout home. Three bedrooms on second floor with nice views. Energy efficient gas heat. Large deck in rear overlooking back yard for

  Terry Cubeddu Ameristar Royal Realty LLC

  34 Rock St, Winsted, CT 06098
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  $27,000

  Sold Apr 10, 2026

  48 Bridge St, Winsted, CT 06098

  • Land
  • 6,534 Sq Ft
  • $180,000 per Acre

  Last Sold Summary

  • 13% Above List Price
  • 359 Days On Market

  Current Estimated Value $27,081

  Last Listing Agent David Sartirana Northwest CT Realty

  48 Bridge St, Winsted, CT 06098
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  Not Listed For Sale

  174 Wallens St Unit C3, Winsted, CT 06098

  • 2 Beds
  • 2.5 Baths
  • 1,946 Sq Ft
  • Built 2005

  174 Wallens St Unit C3, Winsted, CT 06098

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Amanda Balaski Northwest CT Realty
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  /2

  $29,900

  Pending

  • Land
  • 5,662 Sq Ft
  • $230,000 per Acre

  17 Birdsall St, Winsted, CT 06098

  Rare opportunity to build in a convenient in-town location! This level 0.13-acre vacant lot is within walking distance of downtown shopping, dining, and services, while also offering easy access to Highland Lake's public beach, boat launch, and recreational opportunities. This property offers an excellent combination of location and potential. Public water and public sewer are available in the

  

  David Sartirana

  Northwest CT Realty

  17 Birdsall St, Winsted, CT 06098
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  /28

  $1,950 Per Month

  • 2 Beds
  • 2 Baths
  • 1,289 Sq Ft
  • Townhouse for Rent

  59 Cook St Unit 7, Winsted, CT 06098

  Rarely available 2-story townhouse condo for rent! Start your mornings with coffee on the rear deck with a lake view in the distance. This condo features 2 spacious bedrooms and 2 full bathrooms, including a primary suite with a full bath and shower stall. Enjoy easy-to-maintain laminate flooring throughout. The property offers a private 1-car garage plus 2 additional off-street parking spaces in

  Debra Jablonski Berkshire Hathaway NE Prop.

  59 Cook St Unit 7, Winsted, CT 06098
• 

  $1,200,000

  Sold May 20, 2026

  722 Lake Dr, Winsted, CT 06098

  • 3 Beds
  • 2.5 Baths
  • 1,556 Sq Ft
  • Built 2014

  Last Sold Summary

  • $771/SF
  • 1 Day On Market

  Current Estimated Value $1,199,116

  Last Listing Agent Joanne Donne The Washington Agency

  722 Lake Dr, Winsted, CT 06098
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  Est $701,350

  Not Listed For Sale

  102 Hollow Hill Rd, Winsted, CT 06098

  • 3 Beds
  • 2.5 Baths
  • 2,692 Sq Ft
  • Built 2004

  102 Hollow Hill Rd, Winsted, CT 06098

  Last Sold Summary

  • 49 Days On Market

  Last Listing Agent Dawn Rousseau Showcase Realty, Inc.
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  /2

  $29,000

  Pending

  • Land
  • 5,227 Sq Ft
  • $241,667 per Acre

  82-84 Rockwell St, Winchester, CT 06098

  Rare opportunity to build in a convenient in-town location! This level 0.12-acre vacant lot is within walking distance of downtown shopping, dining, and services, while also offering easy access to Highland Lake's public beach, boat launch, and recreational opportunities. This property offers an excellent combination of location and potential. Public water and public sewer are available in the

  

  David Sartirana

  Northwest CT Realty

  82-84 Rockwell St, Winchester, CT 06098
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  $227,500

  Sold Nov 20, 2025

  174 Wallens St Unit H1, Winsted, CT 06098

  • 1 Bed
  • 2 Baths
  • 1,334 Sq Ft
  • Built 2007

  Last Sold Summary

  • 3% Below List Price
  • $171/SF
  • 91 Days On Market

  Last Listing Agent Kim D'Andrea William Pitt Sotheby's Int'l

  174 Wallens St Unit H1, Winsted, CT 06098
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  Est $289,960

  Not Listed For Sale

  17 Colony Dr, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,040 Sq Ft
  • Built 1965

  17 Colony Dr, Winsted, CT 06098

  Last Sold Summary

  • 72 Days On Market

  Last Listing Agent David Sartirana Northwest CT Realty
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  /30

  $325,000

  Pending

  • 4 Beds
  • 2 Baths
  • 2,103 Sq Ft

  120 E Lake St, Winsted, CT 06098

  Excellent opportunity for both owner-occupants and investors! This well-maintained two-family home features two spacious units, each offering 5 rooms, 2 bedrooms, and 1 full bath. Both apartments showcase beautiful hardwood flooring throughout and are served by separate natural gas heating systems for efficiency and convenience. The upper-level unit includes a charming enclosed porch, providing

  

  David Sartirana

  Northwest CT Realty

  120 E Lake St, Winsted, CT 06098
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  $690,000

  Sold Feb 06, 2026

  151 Losaw Rd, Winsted, CT 06098

  • 5 Beds
  • 2.5 Baths
  • 2,950 Sq Ft
  • Built 2007

  Last Sold Summary

  • 14% Below List Price
  • $234/SF
  • 164 Days On Market

  Current Estimated Value $727,661

  Last Listing Agent Breanna Goebel Compass Connecticut, LLC

  151 Losaw Rd, Winsted, CT 06098
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  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
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  /2

  $45,000

  Pending

  • Land
  • 1.07 Acres
  • $42,056 per Acre

  132 Florence St, Winsted, CT 06098

  Rare opportunity to build your dream home on this 1.07-acre vacant lot conveniently located close to downtown shopping, dining, and everyday amenities. Situated in an established neighborhood, this property offers season-long westerly views and spectacular sunset vistas, creating the perfect backdrop for your future home. Public water and public sewer are available in the street (buyer to verify

  

  David Sartirana

  Northwest CT Realty

  132 Florence St, Winsted, CT 06098
• 

  $277,000

  Sold Oct 09, 2025

  12 Cherry St, Winsted, CT 06098

  • 4 Beds
  • 1 Bath
  • 1,492 Sq Ft
  • Built 1800

  Last Sold Summary

  • 4% Below List Price
  • $186/SF
  • 54 Days On Market

  Current Estimated Value $301,550

  Last Listing Agent Susan MCGHEE The Washington Agency

  12 Cherry St, Winsted, CT 06098
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  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.
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  /5

  $42,900

  $27K PRICE DROP

  • Land
  • 5,227 Sq Ft
  • $357,500 per Acre

  319 White Oak Trail, Winchester, CT 06098

  Wooded interior lot located at the end of a dead-end street, offering a private setting. The parcel is slightly sloped and accessed from the end of the road. Clients, do your homework , including but not limited to surveys, zoning, and building approvals. Convenient location with approximately a 15-minute walk to Resha Beach on Highland Lake for recreational enjoyment. Lake rights are granted to

  Matt Tearman Coldwell Banker Realty

  319 White Oak Trail, Winchester, CT 06098
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  $230,000

  Sold Mar 18, 2026

  106 Rockwell St, Winsted, CT 06098

  • 6 Beds
  • 3 Baths
  • 1,874 Sq Ft
  • Built 1850

  Last Sold Summary

  • 23% Below List Price
  • $123/SF
  • 23 Days On Market

  Current Estimated Value $235,082

  Last Listing Agent Dawn Rousseau Showcase Realty, Inc.

  106 Rockwell St, Winsted, CT 06098
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  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
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  /8

  $499,900

  • 6 Beds
  • 5 Baths
  • 2,864 Sq Ft

  205 Old New Hartford Rd, Winchester, CT 06098

  Charming Multi-Family Property with steady income potential! Welcome to your next lucrative investment venture! Nestled on an expansive 1-acre lot, this multi-family property features 5 distinct living spaces, making it an ideal addition to your real estate portfolio. This property comprises 4 studio apartments and a spacious 2-bedroom apartment, catering to a variety of tenants and maximizing

  TK Krumm Berkshire Hathaway NE Prop.

  205 Old New Hartford Rd, Winchester, CT 06098
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  $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 $395,145

  Last Listing Agent Jessica Washington William Raveis Real Estate

  187 Torringford St, Winsted, CT 06098
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  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
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  /38

  $649,900

  • 2 Beds
  • 1 Bath
  • 1,361 Sq Ft

  600 E Wakefield Blvd, Winsted, CT 06098

  Set along the highly desirable east side of Highland Lake, 600 East Wakefield Boulevard offers a unique opportunity to create a waterfront retreat tailored to your lifestyle. Brimming with charm and character, this home is ready for its next chapter and the fresh vision. Spend your days swimming, boating, and kayaking with easy access to the lake and the added benefit of a semi-private boat

  Stacy Anselmo Coldwell Banker Realty

  600 E Wakefield Blvd, Winsted, CT 06098
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  $315,000

  Sold Apr 09, 2026

  25 Center St, Winsted, CT 06098

  • 3 Beds
  • 2.5 Baths
  • 2,754 Sq Ft
  • Built 1860

  Last Sold Summary

  • 2% Below List Price
  • $114/SF
  • 175 Days On Market

  Last Listing Agent Tony Goia The Washington Agency

  25 Center St, Winsted, CT 06098
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  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
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  /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
• 

  $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 $164,376

  Last Listing Agent Joseph Caslin Sailpoint Property Group

  155 Rockwell St, 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
• 

  

  /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
• 

  $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 $307,743

  Last Listing Agent Alison Behlman Tier 1 Real Estate

  39 Colony Dr, Winsted, CT 06098
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  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
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  /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 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
• 

  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.
• 

  

  /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

Showing Results 41 - 80, Page 2 of 18