Winchester, CT Homes

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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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  /37

  $5,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft
  • House for Rent

  880 W Wakefield Blvd, Winsted, CT 06098

  Available Seasonal lakeside living at its finest with this fully renovated, fully furnished 3 bedroom, sleeps 10, 2 full-baths, family estate set on a half acre of professionally landscaped grounds overlooking picturesque Highland Lake. Located just 0.6 miles from Main Street Winsted and Red Barn Brewing, this property combines serene lakefront living with convenient access to local amenities.

  Matt Crossen Coldwell Banker Realty

  880 W Wakefield Blvd, 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
• 

  Est $171,000

  Not Listed For Sale

  14 Pine Rd, Colebrook, CT 06021

  • 4 Beds
  • Built 1998

  14 Pine Rd, Colebrook, CT 06021

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent LAURA BARTLETT Northwest CT Realty
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  /37

  $250,000

  • Land
  • 9 Acres
  • $27,778 per Acre

  321 Colebrook Rd, Winchester, CT 06098

  321 Colebrook Road is a rare opportunity to own beautiful land with natural features and self-sustaining potential. A natural spring gently rolls through the property, surrounded by mature oak, ash, birch, black walnut, pine, and abundant sugar maple trees - perfect for producing your own maple syrup. The land is rich with native granite and sparkling quartz throughout, adding character and

  

  Ariel Edery

  mygoodagent

  321 Colebrook Rd, Winchester, CT 06098
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  /8

  $1,500 Per Month

  • 2 Beds
  • 1.5 Baths
  • 950 Sq Ft
  • Property for Rent

  936 Main St Unit 12, Winchester, CT 06098

  Recently purchased and re-built manufactured home community in Winsted in final stages of being completed. Beautiful free standing ranch style homes, 2 bedroom with 1 bath and 2 baths available as well as an attached entrance enclosed porch. This is a small manufactured home community. Come see these homes. You can't rent a single-family house as nice as these for the price. As each house has

  Michael Block Building Blocks LLC

  936 Main St Unit 12, Winchester, CT 06098
• 

  $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
• 

  Est $348,371

  Not Listed For Sale

  268 Smith Hill Rd, Colebrook, CT 06021

  • 2 Beds
  • 2 Baths
  • 1,635 Sq Ft
  • Built 1955

  268 Smith Hill Rd, Colebrook, CT 06021

  Last Sold Summary

  • 122 Days On Market

  Last Listing Agent David Sartirana Northwest CT Realty
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  $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
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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
• 

  $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
• 

  Est $112,907

  Not Listed For Sale

  11 Gibbs St Unit 9, Winsted, CT 06098

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft
  • Built 1985

  11 Gibbs St Unit 9, Winsted, CT 06098

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent David Sartirana Northwest CT Realty
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  /2

  $49,000

  Pending

  • Land
  • 2 Acres
  • $24,500 per Acre

  18 Pine Rd, Colebrook, CT 06021

  Discover the perfect setting for your dream home on this private 2.0-acre parcel in the scenic hills of Colebrook. Featuring 236 feet of road frontage on quiet Pine Road, this property offers a beautiful building site situated on a gently elevated plateau with desirable southern and western exposures, providing excellent sunlight and the potential for stunning sunset views. Surrounded by nature

  

  David Sartirana

  Northwest CT Realty

  18 Pine Rd, Colebrook, CT 06021
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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
• 

  $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
• 

  Est $123,659

  Not Listed For Sale

  11 Gibbs St Unit 7, Winsted, CT 06098

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft
  • Built 1984

  11 Gibbs St Unit 7, Winsted, CT 06098

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent David Sartirana Northwest CT Realty
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  $305,000

  $35K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,442 Sq Ft

  103 Cordano Rd, Winsted, CT 06098

  Well-maintained Cape in a desirable rural setting, yet just minutes from shopping, dining, schools, and other everyday conveniences. This 7-room home offers 3 bedrooms and 1.5 baths with a flexible floor plan designed for comfortable living. The main level features a formal living room, dining room, kitchen, family room, primary bedroom, and a full bath w/laundry, providing the convenience of

  

  David Sartirana

  Northwest CT Realty

  103 Cordano Rd, Winsted, CT 06098
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  $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
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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 $107,377

  Not Listed For Sale

  11 Gibbs St Unit 6, Winsted, CT 06098

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft
  • Built 1985

  11 Gibbs St Unit 6, Winsted, CT 06098

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent Amanda Cole Carol Cole Real Estate, LLC
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  /37

  $799,900

  • 2 Beds
  • 1 Bath
  • 1,044 Sq Ft

  804 W Wakefield Blvd, Winsted, CT 06098

  Experience an everyday vacation at 804 W. Wakefield Blvd on beautiful Highland Lake! This exceptional turnkey, year-round waterfront retreat is ideal as a primary residence, weekend escape, vacation home, or income-producing rental. Perfectly positioned on the widest part of Highland Lake's coveted Third Bay, enjoy breathtaking sunrises, panoramic water views, and bald eagles soaring overhead

  

  Pamela Dostilio

  Coldwell Banker Realty

  804 W Wakefield Blvd, 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
• 

  Est $309,830

  Not Listed For Sale

  28 Maloney Ct, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,485 Sq Ft
  • Built 1940

  28 Maloney Ct, Winsted, CT 06098

  Last Sold Summary

  • 59 Days On Market

  Last Listing Agent Beth Cantor Coldwell Banker Realty
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  /37

  $429,000

  $121K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 5,016 Sq Ft

  55 Walnut St, Winsted, CT 06098

  Timeless Victorian with Endless Possibilities.Step into a piece of history with this stunning Victorian property, a landmark in the community and home to The Maloney Funeral Home since the early 1900's. Nestled in the TCR Zone, this versatile building offers a wealth of potential. The TCR Zone allows for accessory residential uses, community centers, family day care homes, single-family

  

  David Sartirana

  Northwest CT Realty

  55 Walnut St, Winsted, CT 06098
• 

  $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 $367,038

  Not Listed For Sale

  103 Shore Dr, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 920 Sq Ft
  • Built 1942

  103 Shore Dr, Winsted, CT 06098

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Kathryn Ekstrom Haynes Real Estate Services
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  /2

  $45,000

  • Land
  • 17,859 Sq Ft
  • $109,756 per Acre

  32 Hubbard St, Winsted, CT 06098

  Rare opportunity to build in a convenient in-town location! This level 0.41-acre lot is ideally situated close to downtown amenities while offering easy access to Highland Lake's public beach and boat launch. Formerly improved with a three-story Colonial home, the property presents a unique opportunity to redevelop an established homesite. Public water, public sewer, and natural gas are available

  

  David Sartirana

  Northwest CT Realty

  32 Hubbard 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 $395,145

  Last Listing Agent Jessica Washington William Raveis Real Estate

  187 Torringford St, 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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  /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
• 

  $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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  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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  /5

  $200,000

  • Land
  • 15.9 Acres
  • $12,579 per Acre

  00 Chapel Rd, Winchester, CT 06098

  Look no further for A Very Private location to build your Dream Home. A Wooded Hill top building site overlooking beautiful Winchester Center which can provide peace and solitude for your home or vacation retreat . Historical Winchester Center is deep with rich heritage and History of Winchester. Convenient access agreement to the Rear lot is though 151 Chapel Rd. property.

  Linda Ganem Borla & Associates Real Estate

  00 Chapel Rd, Winchester, 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 $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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  /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
• 

  $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
• 

  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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  $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
• 

  $320,000

  Sold Sep 03, 2025

  107 Old Rd N, Winchester, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,616 Sq Ft
  • Built 1973

  Last Sold Summary

  • 2% Above List Price
  • $198/SF
  • 24 Days On Market

  Last Listing Agent Jill Rubino Century 21 AllPoints Realty

  107 Old Rd N, Winchester, CT 06098

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