Winchester, CT Homes

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  /26

  $220,000

  • 4 Beds
  • 2 Baths
  • 1,844 Sq Ft

  30 Upland Rd, Winsted, CT 06098

  Located in the charming community of Winsted, this 4-bedroom home is tucked away in a quiet, low-traffic neighborhood while still being close to many local amenities. Hardwood floors run throughout the home, adding warmth and character, and the tree-lined backyard offers a private outdoor setting to enjoy year round. This home also features a beautiful enclosed second-floor sun porch, perfect for

  

  Jeffrey Liskin

  Northwest CT Realty

  30 Upland Rd, Winsted, CT 06098
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  /12

  $1,300 Per Month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • House for Rent

  267 Rockwell St Unit 1st fl, Winsted, CT 06098

  Ground level 1 bedroom 1 bath unit. Walking distance to Highland Lake. Laundry hookups in the unit. No Pets No Smoking, Credit, background, eviction checks, 1st month rent, 2 months security deposit.

  Diane Carroll The Washington Agency

  267 Rockwell St Unit 1st fl, Winsted, 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 $166,000

  Last Listing Agent David Sartirana Northwest CT Realty

  48 Bridge St, Winsted, CT 06098
• 

  Est $701,389

  Not Listed For Sale

  404 Colebrook Rd, Colebrook, CT 06021

  • 3 Beds
  • 2.5 Baths
  • 3,860 Sq Ft
  • Built 1989

  404 Colebrook Rd, Colebrook, CT 06021

  Last Sold Summary

  • 22 Days On Market
• 

  

  

  /8

  $299,900

  Pending

  • 6 Beds
  • 2 Baths
  • 2,699 Sq Ft

  77 Hubbard St, Winsted, CT 06098

  Discover this versatile two-family residence offering a blend of modern updates and timeless charm. Each unit boasts three bedrooms and a full bath, providing ample space and comfort for tenants or multi-generational living. The first-floor unit has been beautifully renovated, featuring a brand-new kitchen with stylish finishes, updated bath, gleaming hardwood floors, and plush new carpet in the

  

  Amy Rio

  Better Homes and Gardens Real Estate Executive Real Estate

  77 Hubbard 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
• 

  $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 $1,189,476

  Last Listing Agent Joanne Donne The Washington Agency

  722 Lake Dr, Winsted, CT 06098
• 

  Est $382,582

  Not Listed For Sale

  98 Pinney St, Colebrook, CT 06021

  • 3 Beds
  • 1 Bath
  • 1,294 Sq Ft
  • Built 1940

  98 Pinney St, Colebrook, CT 06021

  Last Sold Summary

  • 39 Days On Market
• 

  

  /15

  $499,000

  Under Contract

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

  5 Stadler Heights, Winsted, CT 06098

  Spacious and full of potential, this 10-room home offers 4 bedrooms and 2.5 baths with plenty of room for everyone. Priced below current market value, this property presents a fantastic opportunity for buyers willing to make some cosmetic updates and build instant equity. Set in a quiet country location within a private development known for its large lots and peaceful surroundings, the home

  

  David Sartirana

  Northwest CT Realty

  5 Stadler Heights, Winsted, CT 06098
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  /22

  $2,150 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
• 

  $800,000

  Sold Aug 04, 2025

  266 Perch Rock Trail, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • Built 1928

  Last Sold Summary

  • 7% Above List Price
  • $538/SF
  • 0 Days On Market

  Current Estimated Value $818,355

  Last Listing Agent Laurie Murray KW Legacy Partners

  266 Perch Rock Trail, Winsted, CT 06098
• 

  Est $158,000

  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
• 

  

  /26

  $998,000

  Pending

  • 4 Beds
  • 3 Baths
  • 3,330 Sq Ft

  878 W Wakefield Blvd, Winsted, CT 06098

  WATERFRONT AND PRIVACY-WIN, WIN! PACK YOUR CLOTHES AND TOOTHBRUSH, THIS GEM IS TURN KEY AND WAITING FOR YOU! FULLY REMODELED INSIDE AND OUT! Nestled along the shores of HIGHLAND LAKE, this stunning waterfront retreat offers the perfect blend of year-round living and vacation-style comfort. Featuring 4 bedrooms and 3 bathrooms, this spacious home is designed to capture breathtaking lake views

  

  Annie Q Simard

  LPT Realty

  878 W Wakefield Blvd, Winsted, CT 06098
• 

  

  /5

  $1,300 Per Month

  • 1 Bed
  • 1 Bath
  • 595 Sq Ft
  • House for Rent

  43 Wallens St Unit 1, Winsted, CT 06098

  Ranch 1 bedroom 1st fl unit, NO LAUNDRY HOOKUPS, electric heat/hot water. 1st month rent, 2 months security deposit, credit, background, renters insurance & eviction checks required. Available 8/1

  Diane Carroll The Washington Agency

  43 Wallens St Unit 1, 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 $331,180

  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
• 

  /2

  $29,900

  • 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
• 

  $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 $693,841

  Last Listing Agent Breanna Goebel Compass Connecticut, LLC

  151 Losaw Rd, Winsted, CT 06098
• 

  Est $114,802

  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
• 

  /2

  $29,000

  • 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
• 

  $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 $283,046

  Last Listing Agent Susan MCGHEE The Washington Agency

  12 Cherry St, Winsted, CT 06098
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  Est $300,026

  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
• 

  

  /39

  $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
• 

  $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 $229,859

  Last Listing Agent Dawn Rousseau Showcase Realty, Inc.

  106 Rockwell St, Winsted, CT 06098
• 

  Est $330,441

  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
• 

  

  /39

  $369,000

  Under Contract

  • 2 Beds
  • 1.5 Baths
  • 1,440 Sq Ft

  212 Spencer Hill Rd, Winsted, CT 06098

  Nestled on a private lot in scenic Winchester, this beautifully maintained home offers a wonderful blend of comfort, character, and natural surroundings. Hardwood floors welcome you into the bright and inviting interior, where the custom kitchen serves as the heart of the home with hickory cabinetry, granite countertops, tile backsplash, and stainless-steel appliances. The second floor features

  

  David Sartirana

  Northwest CT Realty

  212 Spencer Hill Rd, 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 $371,126

  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
• 

  

  /29

  $325,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,118 Sq Ft

  188 Glendale Ave, Winsted, CT 06098

  Welcome to 188 Glendale Avenue! This charming 3-4 bedroom ranch sits on a quiet cul-de-sac. This home boasts of beautiful evening sunsets and quiet mornings sipping coffee on a secluded backyard patio. There have been many updates added, including vinyl windows, a new circuit panel and a new walk-in shower. Entering the home, you find a cozy living room with a working fireplace. The

  Mary Anne Casey D. Beckley Realty

  188 Glendale Ave, Winsted, 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
• 

  

  /5

  $60,000

  $10K PRICE DROP

  • Land
  • 5,227 Sq Ft
  • $500,000 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
• 

  $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 $188,255

  Last Listing Agent Joseph Caslin Sailpoint Property Group

  155 Rockwell St, Winsted, CT 06098
• 

  Est $285,641

  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
• 

  

  /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
• 

  $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 $287,551

  Last Listing Agent Alison Behlman Tier 1 Real Estate

  39 Colony Dr, Winsted, CT 06098
• 

  Est $259,326

  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
• 

  

  /7

  $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
• 

  $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
• 

  Est $260,400

  Not Listed For Sale

  17 Front St, Winsted, CT 06098

  • 4 Beds
  • 1.5 Baths
  • 1,600 Sq Ft
  • Built 1915

  17 Front St, Winsted, CT 06098

  Last Sold Summary

  • 20 Days On Market

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