5,543

Homes in ZIP Code 06098

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  • 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

    (860) 467-0358

    5 Stadler Heights, Winsted, CT 06098
  • 12 Beach St Unit 7, Winsted, CT 06098
    12 Beach St Unit 7, Winsted, CT 06098
    /2

    $1,050 plus fees

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft
    • Condo for Rent

    12 Beach St Unit 7, Winsted, CT 06098

    Property Id: 1615805Total 8 - 1 BED ROOM UNITS in the building CLOSE to Route 8 & WINSTED Mainstreet, on-site parking, coin operated laundry, REAR BALCONY.

    12 Beach St Unit 7, Winsted, CT 06098
  • 37 Riveredge Dr Unit 37, Winsted, CT 06098

    $160,000 Sold May 07, 2025

    37 Riveredge Dr Unit 37, Winsted, CT 06098

    • 2 Beds
    • 1.5 Baths
    • 992 Sq Ft
    • Built 1986

    Last Sold Summary

    • $161/SF
    • 37 Days On Market

    Current Estimated Value $164,532

    Last Listing Agent Erin Ruwet Century 21 AllPoints Realty

    37 Riveredge Dr Unit 37, Winsted, CT 06098
    • 24 Simons Pond Rd, Colebrook, CT 06021

      Est $371,611 Not Listed For Sale

      24 Simons Pond Rd, Colebrook, CT 06021

      • 2 Beds
      • 2.5 Baths
      • 1,934 Sq Ft
      • Built 1980
      24 Simons Pond Rd, Colebrook, CT 06021

      Last Sold Summary

      • $191/SF
      • 25 Days On Market

      Last Sold Price $370,000

      Last Listing Agent Mimi Harson William Pitt

  • 11 Old Creamery Rd, Colebrook, CT 06021
    11 Old Creamery Rd, Colebrook, CT 06021
    11 Old Creamery Rd, Colebrook, CT 06021
    /39

    $499,000

    • 3 Beds
    • 2 Baths
    • 1,654 Sq Ft

    11 Old Creamery Rd, Colebrook, CT 06021

    FULLY RENOVATED! In addition this home is fully insulated, energy-efficient, and enhanced with solar panels for low utility costs. The open floor plan and cozy fireplace create the perfect space for gatherings, while multiple decks, an above-ground pool, and serene natural surroundings provide a tranquil retreat-ideal for year-round living or a weekend getaway. Located perfectly on a beautiful

    Rodrigo Aguiar William Raveis Real Estate

    11 Old Creamery Rd, Colebrook, CT 06021
  • 440 Main St Unit B, Winchester, CT 06098
    440 Main St Unit B, Winchester, CT 06098
    440 Main St Unit B, Winchester, CT 06098
    /5

    $1,200 per month

    • 2 Beds
    • 1 Bath
    • 4,668 Sq Ft
    • Apartment for Rent

    440 Main St Unit B, Winchester, CT 06098

    Second Floor two Bedroom room apartment set in town. Convenient to stores, restaurants and medical facility.

    Linda Ganem Borla & Associates Real Estate

    440 Main St Unit B, Winchester, CT 06098
  • 704 W Wakefield Blvd, Winsted, CT 06098

    $495,000 Sold Jun 09, 2025

    704 W Wakefield Blvd, Winsted, CT 06098

    • 2 Beds
    • 2 Baths
    • 754 Sq Ft
    • Built 1911

    Last Sold Summary

    • 6% Above List Price
    • $656/SF
    • 4 Days On Market

    Current Estimated Value $482,244

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

    704 W Wakefield Blvd, Winsted, CT 06098
    • 404 Colebrook Rd, Colebrook, CT 06021

      Est $754,977 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

      • 10% Above List Price
      • $178/SF
      • 22 Days On Market

      Last Sold Price $687,000

      Last Listing Agent Lori Meyerson Coldwell Banker Realty

  • 123 Old North Rd, Winsted, CT 06098
    123 Old North Rd, Winsted, CT 06098
    123 Old North Rd, Winsted, CT 06098
    /28

    $425,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,781 Sq Ft

    123 Old North Rd, Winsted, CT 06098

    This one-of-a-kind custom Ranch is tucked well back from the road for exceptional privacy and was thoughtfully designed for its present owner. The stunning kitchen is truly the heart of the home, featuring a dramatic floor-to-ceiling stone fireplace, an expansive island with breakfast bar, an endless array of cabinets, and a built-in range with gas cooktop. The dining area flows seamlessly from

    Rick Berkenstock Century 21 AllPoints Realty

    123 Old North Rd, Winsted, CT 06098
  • 40 High St, Winsted, CT 06098
    40 High St, Winsted, CT 06098
    40 High St, Winsted, CT 06098
    /11

    $850 per month

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

    40 High St, Winsted, CT 06098

    This one bedroom is very tiny, it is approximately 400 square feet. Large kitchen and a living room. Low cost to heat and cool. Brand new kitchen floor. Washer and dryer.

    Alan Hill eXp Realty

    40 High 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 $841,672

    Last Listing Agent Laurie Murray KW Legacy Partners

    266 Perch Rock Trail, Winsted, CT 06098
    • 14 Pine Rd, Colebrook, CT 06021

      Est $201,000 Not Listed For Sale

      14 Pine Rd, Colebrook, CT 06021

      • 4 Beds
      • Built 1998
      14 Pine Rd, Colebrook, CT 06021

      Last Sold Summary

      • 6% Above List Price
      • $54/SF
      • 43 Days On Market

      Last Sold Price $190,000

      Last Listing Agent LAURA BARTLETT Northwest CT Realty

  • 162 Spencer Hill Rd, Winsted, CT 06098
    162 Spencer Hill Rd, Winsted, CT 06098
    162 Spencer Hill Rd, Winsted, CT 06098
    /35

    $625,000 Open Sat 1PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 2,144 Sq Ft

    162 Spencer Hill Rd, Winsted, CT 06098

    Experience the beauty and privacy of this pristine log home set on 16.53 picturesque acres. A long, level gravel driveway welcomes you to the expansive 43' x 8' covered front porch, the perfect place to enjoy breathtaking winter sunrises overlooking your own blueberry bushes. Surrounded by abundant wildlife, this property offers a true country retreat. Inside, you'll find soaring ceilings, a

    Kelly Sullivan Sullivan Real Estate Inc

    162 Spencer Hill Rd, Winsted, CT 06098
  • 91 Williams Ave, Winsted, CT 06098
    91 Williams Ave, Winsted, CT 06098
    91 Williams Ave, Winsted, CT 06098
    /37

    $2,450 per month

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • House for Rent

    91 Williams Ave, Winsted, CT 06098

    Welcome to this beautifully remodeled and spacious 3-bedroom, 2 full bathroom home in the heart of Winchester. Featuring hardwood floors throughout both the first and second levels, this home offers a warm and inviting layout with an eat-in kitchen that has a center island perfect for everyday living. Enjoy the convenience of a separate laundry room-washer and dryer included, high-efficiency gas

    Suzie Larson Turning Point Realty, LLC

    91 Williams Ave, Winsted, CT 06098
  • 39 Finn St, Winsted, CT 06098

    $269,000 Sold May 05, 2025

    39 Finn St, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 1,175 Sq Ft
    • Built 1880

    Last Sold Summary

    • $229/SF
    • 35 Days On Market

    Current Estimated Value $267,759

    Last Listing Agent Christine Hunter Hunter Real Estate, LLC

    39 Finn St, Winsted, CT 06098
    • 268 Smith Hill Rd, Colebrook, CT 06021

      Est $321,014 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

      • 1% Below List Price
      • $199/SF
      • 122 Days On Market

      Last Sold Price $324,900

      Last Listing Agent David Sartirana Northwest CT Realty

  • 118 South Rd, Winsted, CT 06098
    118 South Rd, Winsted, CT 06098
    118 South Rd, Winsted, CT 06098
    /36

    $419,000 Open Sun 11AM - 2PM

    • 4 Beds
    • 3 Baths
    • 2,240 Sq Ft

    118 South Rd, Winsted, CT 06098

    Tucked away in a peaceful country setting just minutes from Winchester Center, this well-maintained 4-bedroom Colonial offers space, comfort, and timeless charm. Proudly owned by just one owner, this home reflects true pride of ownership throughout, with thoughtfully updated mechanicals and the added peace of mind of a whole-house generator. The inviting main level features a spacious family room

    Becky Grieco Berkshire Hathaway NE Prop.

    118 South Rd, Winsted, CT 06098
  • 22 Upson Ave, Winsted, CT 06098
    22 Upson Ave, Winsted, CT 06098
    22 Upson Ave, Winsted, CT 06098
    /10

    $1,500 per month

    • 2 Beds
    • 1 Bath
    • 1,199 Sq Ft
    • House for Rent

    22 Upson Ave, Winsted, CT 06098

    Beautiful First-Floor Apartment with Classic Charm and Modern Updates! This spacious first-floor apartment features gleaming hardwood floors, fresh paint, and an updated kitchen. Enjoy the high ceilings and beautiful woodwork that add character and warmth throughout. Conveniently located close to downtown, offering easy access to shopping, dining, and commuting routes.

    Kelly Sullivan Sullivan Real Estate Inc

    22 Upson Ave, Winsted, CT 06098
  • 830 Main St, Winsted, CT 06098

    $220,000 Sold Apr 24, 2025

    830 Main St, Winsted, CT 06098

    • 5 Beds
    • 4 Baths
    • 3,115 Sq Ft
    • Built 1900

    Last Sold Summary

    • 2% Below List Price
    • $71/SF
    • 14 Days On Market

    Current Estimated Value $221,942

    Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

    830 Main St, Winsted, CT 06098
    • 11 Gibbs St Unit 6, Winsted, CT 06098

      Est $113,421 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

      • 22% Above List Price
      • $163/SF
      • 62 Days On Market

      Last Sold Price $93,000

      Last Listing Agent Amanda Cole Carol Cole Real Estate, LLC

  • 262 Holabird Ave, Winsted, CT 06098
    262 Holabird Ave, Winsted, CT 06098
    262 Holabird Ave, Winsted, CT 06098
    /21

    $360,000 Pending

    • 3 Beds
    • 1.5 Baths
    • 1,312 Sq Ft

    262 Holabird Ave, Winsted, CT 06098

    Discover the perfect blend of small time charm with many conveniences close at hand! This well maintained, warm and inviting, 1 owner home offers it all! Having beautiful Highland Lake in this community is certainly one of many pluses! The renovated eat in kitchen offers granite counter tops, stainless steel appliances and access to a beautiful new Trex deck! Along with new decking, new windows

    Mary Anne Casey D. Beckley Realty

    262 Holabird Ave, 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

    $4,000 per month

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

    880 W Wakefield Blvd, Winsted, CT 06098

    Discover 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. Enjoy use of

    Matt Crossen Coldwell Banker Realty

    880 W Wakefield Blvd, 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
    • 28 Maloney Ct, Winsted, CT 06098

      Est $293,017 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

      • 9% Above List Price
      • $182/SF
      • 59 Days On Market

      Last Sold Price $270,000

      Last Listing Agent Beth Cantor Coldwell Banker

  • 156 Shore Dr, Winsted, CT 06098
    156 Shore Dr, Winsted, CT 06098
    156 Shore Dr, Winsted, CT 06098
    /37

    $779,900

    • 5 Beds
    • 1.5 Baths
    • 1,258 Sq Ft

    156 Shore Dr, Winsted, CT 06098

    Summer is just around the corner, and this is your opportunity to own a highly sought-after waterfront property on the beautiful Highland Lake! Located on Shore Drive in the 1st Bay, this private 5-bedroom home offers breathtaking western exposure, giving you the perfect view of every sunset. Enjoy direct waterfront access and make the most of the flat, easy-to-maintain lot - ideal for outdoor

    Bryan Palladino Showcase Realty, Inc.

    156 Shore Dr, Winsted, CT 06098
  • 154 Wallens St, Winsted, CT 06098

    $190,000 Sold May 15, 2025

    154 Wallens St, Winsted, CT 06098

    • 4 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 1905

    Last Sold Summary

    • 13% Below List Price
    • $103/SF
    • 20 Days On Market

    Current Estimated Value $195,236

    Last Listing Agent Adam Devine Dorrance Realty

    154 Wallens St, Winsted, CT 06098
    • 103 Shore Dr, Winsted, CT 06098

      Est $328,073 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

      • 1% Below List Price
      • $359/SF
      • 19 Days On Market

      Last Sold Price $330,000

      Last Listing Agent Kathryn Ekstrom Haynes Real Estate Services

  • 230 E Wakefield Blvd, Winsted, CT 06098
    230 E Wakefield Blvd, Winsted, CT 06098
    230 E Wakefield Blvd, Winsted, CT 06098
    /12

    $314,000 Under Contract

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

    230 E Wakefield Blvd, Winsted, CT 06098

    This Highland Lake house is in great condition, remodeled 4 years ago. Lower level has a separate entrance and was revamped with large living room and full bathroom. Walk to the Association beach in 5 mins.

    Peter D'Addeo Commercial Services Realty

    230 E Wakefield Blvd, Winsted, 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 $689,046

    Last Listing Agent Breanna Goebel Compass Connecticut, LLC

    151 Losaw Rd, Winsted, CT 06098
    • 139 Boyd St, Winsted, CT 06098

      Est $301,049 Not Listed For Sale

      139 Boyd St, Winsted, CT 06098

      • 4 Beds
      • 2 Baths
      • 2,104 Sq Ft
      • Built 1885
      139 Boyd St, Winsted, CT 06098

      Last Sold Summary

      • 28% Above List Price
      • $112/SF
      • 29 Days On Market

      Last Sold Price $235,000

      Last Listing Agent Mary Mary LeBlanc Realty

  • 11 Shantry Rd, Colebrook, CT 06021
    11 Shantry Rd, Colebrook, CT 06021
    11 Shantry Rd, Colebrook, CT 06021
    /15

    $980,000

    • 3 Beds
    • 1.5 Baths
    • 1,443 Sq Ft

    11 Shantry Rd, Colebrook, CT 06021

    Unique property with 149+/- acres, open meadow, abundant standing softwoods and hardwoods, old logging roads, hiking trails, a brook and frontage on 3 roads. House is in need of TLC or tear down and rebuild your dream house, many outbuildings include chicken coop, large livestock barn and sheds. Property is unique and will need work but possibilities are endless.

    LAURA BARTLETT Northwest CT Realty

    11 Shantry Rd, Colebrook, CT 06021
  • 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 $289,522

    Last Listing Agent Susan MCGHEE The Washington Agency

    12 Cherry St, Winsted, CT 06098
    • 174 Wallens St Unit D2, Winsted, CT 06098

      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

      • 6% Above List Price
      • $166/SF
      • 39 Days On Market

      Last Sold Price $225,000

      Last Listing Agent Ashley Church Turning Point Realty, LLC

  • 129 E Lake St, Winsted, CT 06098
    129 E Lake St, Winsted, CT 06098
    129 E Lake St, Winsted, CT 06098
    /35

    $1,495,000

    • 3 Beds
    • 3.5 Baths
    • 2,699 Sq Ft

    129 E Lake St, Winsted, CT 06098

    A true vacation retreat on the shore of Highland Lake! Rare offering in exceptional condition ready for summer enjoyment. Central AC/heat with an open floorplan offering spacious family and entertaining opportunity. Folding glass doors to large lakefront deck with panoramic views of the water. Original house completely renovated inside and out in 2016, with recent stone patio and fire pit added

    KAREN NEWTON William Pitt Sotheby's Int'l

    129 E Lake St, Winsted, CT 06098
  • 14 Riveredge Dr Unit 14, Winsted, CT 06098

    $160,000 Sold Apr 29, 2025

    14 Riveredge Dr Unit 14, Winsted, CT 06098

    • 2 Beds
    • 1.5 Baths
    • 992 Sq Ft
    • Built 1986

    Last Sold Summary

    • $161/SF
    • 0 Days On Market

    Current Estimated Value $163,130

    Last Listing Agent Maria Smith KW Legacy Partners

    14 Riveredge Dr Unit 14, Winsted, CT 06098
    • 174 Wallens St Unit C3, Winsted, CT 06098

      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

      • 14% Above List Price
      • $128/SF
      • 9 Days On Market

      Last Sold Price $250,000

      Last Listing Agent Amanda Balaski Northwest CT Realty

  • 90 Colony Dr, Winsted, CT 06098
    90 Colony Dr, Winsted, CT 06098
    90 Colony Dr, Winsted, CT 06098
    /22

    $335,000

    • 3 Beds
    • 1 Bath
    • 1,282 Sq Ft

    90 Colony Dr, Winsted, CT 06098

    Turnkey Winsted gem completely renovated inside & out! Get ready to just move and and not worry. Here is a beautifully reimagined 3-bedroom, 1-bathroom property in Winsted, offering the perfect blend of modern luxury and ultimate peace of mind. Every detail has been thoughtfully updated to create a true turnkey experience. Step inside to a bright, inviting space where the wall between the

    Michelle Grant Coldwell Banker Premier Real Estate

    90 Colony Dr, 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 $280,043

    Last Listing Agent Dawn Rousseau Showcase Realty, Inc.

    106 Rockwell St, Winsted, CT 06098
    • 17 Colony Dr, Winsted, CT 06098

      Est $281,174 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

      • 14% Above List Price
      • $238/SF
      • 72 Days On Market

      Last Sold Price $247,000

      Last Listing Agent David Sartirana Northwest CT Realty

  • 7 Stadler Heights, Winsted, CT 06098
    7 Stadler Heights, Winsted, CT 06098
    7 Stadler Heights, Winsted, CT 06098
    /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

Showing Results 41 - 80, Page 2 of 18

Connecticut Litchfield County Winsted 06098

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