4,852

Winsted, CT Homes

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  • 77 Hubbard St, Winsted, CT 06098
    77 Hubbard St, Winsted, CT 06098
    77 Hubbard St, Winsted, CT 06098
    /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

    Agent Photo

    Amy Rio

    Better Homes and Gardens Real Estate Executive Real Estate

    77 Hubbard St, Winsted, CT 06098
  • 267 Rockwell St Unit 1st fl, Winsted, CT 06098
    267 Rockwell St Unit 1st fl, Winsted, CT 06098
    267 Rockwell St Unit 1st fl, Winsted, CT 06098
    /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
  • 48 Bridge St, 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
  • 5 Stadler Heights, Winsted, CT 06098
    5 Stadler Heights, Winsted, CT 06098
    5 Stadler Heights, Winsted, CT 06098
    /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

    Agent Photo

    David Sartirana

    Northwest CT Realty

    5 Stadler Heights, Winsted, CT 06098
  • 880 W Wakefield Blvd, Winsted, CT 06098
    880 W Wakefield Blvd, Winsted, CT 06098
    880 W Wakefield Blvd, Winsted, CT 06098
    /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
  • 722 Lake Dr, 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
  • 878 W Wakefield Blvd, Winsted, CT 06098
    878 W Wakefield Blvd, Winsted, CT 06098
    878 W Wakefield Blvd, Winsted, CT 06098
    /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

    Agent Photo

    Annie Q Simard

    LPT Realty

    878 W Wakefield Blvd, Winsted, CT 06098
  • 34 Rock St, Winsted, CT 06098
    34 Rock St, Winsted, CT 06098
    34 Rock St, Winsted, CT 06098
    /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
  • 266 Perch Rock Trail, 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
  • 17 Birdsall St, Winsted, CT 06098
    17 Birdsall St, Winsted, CT 06098
    /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

    Agent Photo

    David Sartirana

    Northwest CT Realty

    17 Birdsall St, Winsted, CT 06098
  • 43 Wallens St Unit 1, Winsted, CT 06098
    43 Wallens St Unit 1, Winsted, CT 06098
    43 Wallens St Unit 1, 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
  • 174 Wallens St Unit H1, 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
  • 82-84 Rockwell St, Winchester, CT 06098
    82-84 Rockwell St, Winchester, CT 06098
    /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

    Agent Photo

    David Sartirana

    Northwest CT Realty

    82-84 Rockwell St, Winchester, CT 06098
  • 151 Losaw Rd, 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
  • 212 Spencer Hill Rd, Winsted, CT 06098
    212 Spencer Hill Rd, Winsted, CT 06098
    212 Spencer Hill Rd, Winsted, CT 06098
    /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

    Agent Photo

    David Sartirana

    Northwest CT Realty

    212 Spencer Hill Rd, Winsted, CT 06098
  • 12 Cherry 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 $283,046

    Last Listing Agent Susan MCGHEE The Washington Agency

    12 Cherry St, Winsted, CT 06098
    • 17 Colony Dr, 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

  • 188 Glendale Ave, Winsted, CT 06098
    188 Glendale Ave, Winsted, CT 06098
    188 Glendale Ave, Winsted, CT 06098
    /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
  • 106 Rockwell 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 $229,859

    Last Listing Agent Dawn Rousseau Showcase Realty, Inc.

    106 Rockwell St, Winsted, CT 06098
    • 159 Pratt St, 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

  • 319 White Oak Trail, Winchester, CT 06098
    319 White Oak Trail, Winchester, CT 06098
    319 White Oak Trail, Winchester, CT 06098
    /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
  • 187 Torringford 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 $371,126

    Last Listing Agent Jessica Washington William Raveis Real Estate

    187 Torringford St, Winsted, CT 06098
    • 17 Front St, Winsted, 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

  • 205 Old New Hartford Rd, Winchester, CT 06098
    205 Old New Hartford Rd, Winchester, CT 06098
    205 Old New Hartford Rd, Winchester, CT 06098
    /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
  • 25 Center St, 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
  • 104 Maloney Ct, Winsted, CT 06098
    104 Maloney Ct, Winsted, CT 06098
    104 Maloney Ct, Winsted, CT 06098
    /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
  • 155 Rockwell St, 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 $188,255

    Last Listing Agent Joseph Caslin Sailpoint Property Group

    155 Rockwell St, Winsted, CT 06098
    • 58 Cherry St, 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

  • 441 Platt Hill Rd, Winsted, CT 06098
    441 Platt Hill Rd, Winsted, CT 06098
    441 Platt Hill Rd, Winsted, CT 06098
    /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
  • 39 Colony Dr, 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 $287,551

    Last Listing Agent Alison Behlman Tier 1 Real Estate

    39 Colony Dr, Winsted, CT 06098
  • 68 Wetmore Ave, Winsted, CT 06098
    68 Wetmore Ave, Winsted, CT 06098
    68 Wetmore Ave, Winsted, CT 06098
    /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
  • 621 Wynne 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 $330,885

    Last Listing Agent David Sartirana Northwest CT Realty

    621 Wynne Rd, Winsted, CT 06098
    • 153 Mathew Rd, Winsted, 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

Showing Results 41 - 80, Page 2 of 18

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