5,120

Winchester, CT Homes

Section Image
  • 256 Colebrook Rd, Winchester Center, CT 06098

    $33,500

    Sold Mar 20, 2026

    256 Colebrook Rd, Winchester Center, CT 06098

    • Land
    • 40,075 Sq Ft
    • $36,413 per Acre

    Last Sold Summary

    • 16% Below List Price
    • 226 Days On Market

    Current Estimated Value $44,000

    Last Listing Agent Austin Brochu Sullivan Real Estate Inc

    256 Colebrook Rd, Winchester Center, CT 06098
    • 11 Orchard St, Winsted, CT 06098

      Est $211,656

      Not Listed For Sale

      11 Orchard St, Winsted, CT 06098

      • 3 Beds
      • 1 Bath
      • 1,759 Sq Ft
      • Built 1900
      11 Orchard St, Winsted, CT 06098

      Last Sold Summary

      • 29% Above List Price
      • $93/SF
      • 19 Days On Market
      • Last Sold Price $164,000
      • Apr 29, 2024

      Last Listing Agent Jonathan Gineo Silver and Oak Realty

  • /2

    $299,900

    • Land
    • 34 Acres
    • $8,821 per Acre

    00 Ramsgate Ln, Barkhamsted, CT 06063

    30 +/- acres in ideal location in Barkhamsted bordering American Legion State Forest in the rear. Minutes from historic Riverton Center and world-renowned fly fishing. Many outdoor activities close by including hiking, biking, tubing, skiing, boating and many more. Land is ideal for almost any application, subdividing, recreation, horses, etc. Land will be subdivided upon contract and prior to

    Heidi Picard-Ramsay Berkshire Hathaway NE Prop.

    00 Ramsgate Ln, Barkhamsted, CT 06063
  • 819 E Wakefield Blvd, Winsted, CT 06098

    $439,900

    Sold Dec 04, 2025

    819 E Wakefield Blvd, Winsted, CT 06098

    • 3 Beds
    • 1.5 Baths
    • 1,892 Sq Ft
    • Built 1920

    Last Sold Summary

    • 12% Below List Price
    • $233/SF
    • 72 Days On Market

    Current Estimated Value $464,088

    Last Listing Agent David Sartirana Northwest CT Realty

    819 E Wakefield Blvd, Winsted, CT 06098
    • 303 E Wakefield Blvd, Winsted, CT 06098

      Est $274,885

      Not Listed For Sale

      303 E Wakefield Blvd, Winsted, CT 06098

      • 2 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1986
      303 E Wakefield Blvd, Winsted, CT 06098

      Last Sold Summary

      • $286/SF
      • 21 Days On Market
      • Last Sold Price $275,000
      • Nov 06, 2024

      Last Listing Agent Tammy Schaller William Raveis Real Estate

  • /26

    $239,000

    Under Contract
    • 7 Beds
    • 3 Baths
    • 2,400 Sq Ft

    Unlisted Address

    Brand new to the market. Must see large 2 story Colonial featuring 13 rooms, 7 Bedrooms, 3 Bathrooms, Walk up attic and full basement. Includes a 2 story barn. Convenient location in the heart of town lends itself to easy access to many nearby amenities. As an investment this residence also has great potential to convert to a multi family home or could be renovated for commercial office space.

    Frank J. Berg Broker/Owner Town & Country Real Estate

    Unlisted Address
  • 111 Torringford St Unit 25, Winsted, CT 06098

    $190,000

    Sold Oct 20, 2025

    111 Torringford St Unit 25, Winsted, CT 06098

    • 2 Beds
    • 2 Baths
    • 1,156 Sq Ft
    • Built 1987

    Last Sold Summary

    • 6% Above List Price
    • $164/SF
    • 2 Days On Market

    Current Estimated Value $190,623

    Last Listing Agent Ron Rudek Connecticut Realty, LLC

    111 Torringford St Unit 25, Winsted, CT 06098
    • 151 Hinsdale Ave, Winsted, CT 06098

      Est $262,765

      Not Listed For Sale

      151 Hinsdale Ave, Winsted, CT 06098

      • 3 Beds
      • 2 Baths
      • 1,634 Sq Ft
      • Built 1948
      151 Hinsdale Ave, Winsted, CT 06098

      Last Sold Summary

      • 19% Above List Price
      • $135/SF
      • 154 Days On Market
      • Last Sold Price $220,000
      • Sep 11, 2023

      Last Listing Agent Sarah Isabella Glenstone Real Estate LLC

  • /36

    $419,000

    Under Contract
    • 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
  • 210 Walnut St, Winsted, CT 06098

    $240,000

    Sold Oct 22, 2025

    210 Walnut St, Winsted, CT 06098

    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft
    • Built 1988

    Last Sold Summary

    • 7% Above List Price
    • $227/SF
    • 46 Days On Market

    Current Estimated Value $243,828

    Last Listing Agent Nicole Araujo Trend 2000 Real Estate

    210 Walnut St, Winsted, CT 06098
    • 111 Riverton Rd Unit 83, Winsted, CT 06098

      Est $197,401

      Not Listed For Sale

      111 Riverton Rd Unit 83, Winsted, CT 06098

      • 2 Beds
      • 1.5 Baths
      • 1,204 Sq Ft
      • Built 1987
      111 Riverton Rd Unit 83, Winsted, CT 06098

      Last Sold Summary

      • 1% Below List Price
      • $166/SF
      • 65 Days On Market
      • Last Sold Price $200,000
      • Dec 13, 2024

      Last Listing Agent David Sartirana Northwest CT Realty

  • /34

    $399,000

    Under Contract
    • 5 Beds
    • 4 Baths
    • 2,779 Sq Ft

    217 Walnut St, Winsted, CT 06098

    In-Town Victorian 2-Family - Exceptional Condition & Versatility Rare opportunity to own a beautifully maintained, vinyl-sided Victorian-style side-by-side two-family home in a prime in-town location! This unique property offers incredible flexibility for investors, owner-occupants, or multi-generational living. Each unit features its own private entrance and spacious layout-one side offering a

    David D'Amore Northwest CT Realty

    217 Walnut St, Winsted, CT 06098
  • 355 W Lake St, Winsted, CT 06098

    $950,000

    Sold Jun 27, 2025

    355 W Lake St, Winsted, CT 06098

    • 5 Beds
    • 3.5 Baths
    • 3,216 Sq Ft
    • Built 2008

    Last Sold Summary

    • 3% Below List Price
    • $295/SF
    • 55 Days On Market

    Current Estimated Value $889,489

    Last Listing Agent David Sartirana Northwest CT Realty

    355 W Lake St, Winsted, CT 06098
    • 16 Alexandria Dr, Winsted, CT 06063

      Est $523,636

      Not Listed For Sale

      16 Alexandria Dr, Winsted, CT 06063

      • 4 Beds
      • 2.5 Baths
      • 2,364 Sq Ft
      • Built 1989
      16 Alexandria Dr, Winsted, CT 06063

      Last Sold Summary

      • 25% Above List Price
      • $177/SF
      • 17 Days On Market
      • Last Sold Price $418,000
      • Sep 01, 2023

      Last Listing Agent Gina Beiser Executive Real Estate

  • /27

    $375,000

    Pending
    • 3 Beds
    • 3,660 Sq Ft

    57 Main St, Winsted, CT 06098

    Wonderful multiuse property on Main St. in Winsted. Currently used as a cleaners on the first floor and residential unit on the second floor. Multiple possibilities for this building which is in a prime location. Potential to take over the current business and rent or live in second floor, covert to multifamily or start a new business venture. This property is also listed as commercial with MLS

    Stacy LaQuerre Regall Realty, LLC

    57 Main St, Winsted, CT 06098
  • 99 Norfolk Rd, Winsted, CT 06098

    $180,000

    Sold Dec 19, 2025

    99 Norfolk Rd, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 980 Sq Ft
    • Built 1948

    Last Sold Summary

    • 23% Below List Price
    • $184/SF
    • 156 Days On Market

    Current Estimated Value $188,393

    Last Listing Agent Lisa McCarthy Coldwell Banker Realty

    99 Norfolk Rd, Winsted, CT 06098
    • 5 Hillside Ave, Winsted, CT 06098

      Est $332,471

      Not Listed For Sale

      5 Hillside Ave, Winsted, CT 06098

      • 4 Beds
      • 2 Baths
      • 2,664 Sq Ft
      • Built 1900
      5 Hillside Ave, Winsted, CT 06098

      Last Sold Summary

      • 17% Above List Price
      • $106/SF
      • 52 Days On Market
      • Last Sold Price $283,500
      • Nov 03, 2023

      Last Listing Agent David Sartirana Northwest CT Realty

  • /31

    $269,999

    $20K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,652 Sq Ft

    118 Meadow St, Winsted, CT 06098

    This charming historic home, built in 1860, blends timeless character with thoughtful updates. Featuring 3-4 bedrooms, this property offers flexible living space to meet your needs. The beautifully remodeled upstairs bathroom is a standout feature, offering modern comfort within this classic home. Enjoy your LARGE eat-in kitchen with laundry hook ups and plenty of natural lighting and ample

    Ashley Henry The Washington Agency

    118 Meadow St, Winsted, CT 06098
  • 35 Glendale Ave, Winsted, CT 06098

    $410,000

    Sold Apr 13, 2026

    35 Glendale Ave, Winsted, CT 06098

    • 3 Beds
    • 2 Baths
    • 2,196 Sq Ft
    • Built 1955

    Last Sold Summary

    • 3% Above List Price
    • $187/SF
    • 35 Days On Market

    Current Estimated Value $392,265

    Last Listing Agent David Sartirana Northwest CT Realty

    35 Glendale Ave, Winsted, CT 06098
    • 36 S Main St, Winsted, CT 06098

      Est $227,546

      Not Listed For Sale

      36 S Main St, Winsted, CT 06098

      • 3 Beds
      • 1.5 Baths
      • 1,380 Sq Ft
      • Built 1920
      36 S Main St, Winsted, CT 06098

      Last Sold Summary

      • 17% Above List Price
      • $141/SF
      • 73 Days On Market
      • Last Sold Price $194,000
      • Sep 21, 2023

      Last Listing Agent DeVante Roman eXp Realty

  • /29

    $299,900

    • 2 Beds
    • 1 Bath
    • 702 Sq Ft

    147 E Wakefield Blvd, Winsted, CT 06098

    Come enjoy Highland Lake living just in time for Summer. Relax in this one level living, cozy cottage home with views of the lake from your deck and just a short distance to Resha beach. Enter through a large mudroom to your open living room with large window to let in natural light, updated kitchen, 2 bedrooms, 1 full bath, main level laundry, front and rear deck, large yard & shed. New flooring

    Mary Mary LeBlanc Realty

    147 E Wakefield Blvd, Winsted, CT 06098
  • 399 Colebrook Rd, Colebrook, CT 06021

    $860,000

    Sold Jun 24, 2025

    399 Colebrook Rd, Colebrook, CT 06021

    • 4 Beds
    • 3 Baths
    • 3,016 Sq Ft
    • Built 1956

    Last Sold Summary

    • 7% Below List Price
    • $285/SF
    • 90 Days On Market

    Current Estimated Value $893,635

    Last Listing Agent David Taylor Elyse Harney Real Estate

    399 Colebrook Rd, Colebrook, CT 06021
    • 111 Riverton Rd Unit 55, Winsted, CT 06098

      Est $198,448

      Not Listed For Sale

      111 Riverton Rd Unit 55, Winsted, CT 06098

      • 2 Beds
      • 1.5 Baths
      • 1,204 Sq Ft
      • Built 1987
      111 Riverton Rd Unit 55, Winsted, CT 06098

      Last Sold Summary

      • 9% Above List Price
      • $151/SF
      • 87 Days On Market
      • Last Sold Price $182,000
      • Apr 26, 2024

      Last Listing Agent Suzie Larson Turning Point Realty, LLC

  • /37

    $765,000

    • 3 Beds
    • 2.5 Baths
    • 4,387 Sq Ft

    184 Smith Hill Rd, Winsted, CT 06098

    Beautiful Private Brick/Clapboard Tudor set back on 8.46 private acres (which includes an extra 2+ acre abutting lot). New Hand Split Cedar Shingled Roof and new rebuilt brick chimney set off this custom elegant home. All warm cherry wood floors and special custom moldings throughout the home add charm. Classy center island Kit with new subzero, granite counters & bow window-Fireplaced Dining

    Mary New Berkshire Hathaway NE Prop.

    184 Smith Hill Rd, Winsted, CT 06098
  • 538 Wheelers Point, Winsted, CT 06098

    $1,500,000

    Sold Oct 14, 2025

    538 Wheelers Point, Winsted, CT 06098

    • 4 Beds
    • 3 Baths
    • 2,496 Sq Ft
    • Built 1930

    Last Sold Summary

    • 20% Below List Price
    • $601/SF
    • 292 Days On Market

    Current Estimated Value $1,498,289

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

    538 Wheelers Point, Winsted, CT 06098
    • 111 Riverton Rd Unit 45, Winsted, CT 06098

      Est $204,185

      Not Listed For Sale

      111 Riverton Rd Unit 45, Winsted, CT 06098

      • 2 Beds
      • 1.5 Baths
      • 1,204 Sq Ft
      • Built 1987
      111 Riverton Rd Unit 45, Winsted, CT 06098

      Last Sold Summary

      • 5% Below List Price
      • $179/SF
      • 4 Days On Market
      • Last Sold Price $215,000
      • Aug 30, 2024

      Last Listing Agent ROBERT SZABO Szabo Realty

  • /36

    $1,850,000

    • 9 Beds
    • 5.5 Baths
    • 7,000 Sq Ft

    431 W Wakefield Blvd, Winsted, CT 06098

    Live the Highland Lake Dream - 431 W. Wakefield Blvd, Winchester, CT Summer is just around the corner - and in Winsted, resort living never ends. Recently named one of the most desirable towns to live in, with the breathtaking Highland Lake at its heart, Winchester offers the perfect blend of beauty and lifestyle. This waterfront estate at 431 W. Wakefield Blvd isn't just a home - it's your

    Lisa Ogren Berkshire Hathaway NE Prop.

    431 W Wakefield Blvd, Winsted, CT 06098
  • 130 Stanton Ave, Winsted, CT 06098

    $225,000

    Sold Nov 03, 2025

    130 Stanton Ave, Winsted, CT 06098

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Built 1979

    Last Sold Summary

    • 4% Below List Price
    • $293/SF
    • 115 Days On Market

    Current Estimated Value $236,103

    Last Listing Agent David D'Amore Northwest CT Realty

    130 Stanton Ave, Winsted, CT 06098
    • 9 Fruit St, Winsted, CT 06098

      Est $248,944

      Not Listed For Sale

      9 Fruit St, Winsted, CT 06098

      • 4 Beds
      • 2 Baths
      • 2,472 Sq Ft
      • Built 1900
      9 Fruit St, Winsted, CT 06098

      Last Sold Summary

      • 39% Above List Price
      • $72/SF
      • 35 Days On Market
      • Last Sold Price $178,550
      • Jul 13, 2023

      Last Listing Agent Michael J Flaherty Jr Sullivan Real Estate Inc

  • /19

    $579,000

    • 11 Beds
    • 5.5 Baths
    • 5,233 Sq Ft

    150 Oak St, Winsted, CT 06098

    150 Oak St. is a fully rented, rare, charming 1920's 5-family apartment home located in a beautiful residential neighborhood in Winsted/Winchester, CT. Old World charm with original woodwork, high ceilings, mostly hardwood floors, and hallways connecting the spacious rooms in 4 of the units -which feature 2 bedrooms and a dining room. The 5th floor is a 3 bedroom, 1 1/2 bath unit with electric

    Pamela Silvestri Turning Point Realty, LLC

    150 Oak St, Winsted, CT 06098
  • 126 Williams Ave, Winsted, CT 06098

    $292,000

    Sold Jul 25, 2025

    126 Williams Ave, Winsted, CT 06098

    • 6 Beds
    • 2 Baths
    • 2,225 Sq Ft
    • Built 1890

    Last Sold Summary

    • 2% Above List Price
    • $131/SF
    • 42 Days On Market

    Current Estimated Value $289,031

    Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

    126 Williams Ave, Winsted, CT 06098
    • 202 Old New Hartford Rd, Winsted, CT 06098

      Est $309,313

      Not Listed For Sale

      202 Old New Hartford Rd, Winsted, CT 06098

      • 4 Beds
      • 1.5 Baths
      • 1,560 Sq Ft
      • Built 1900
      202 Old New Hartford Rd, Winsted, CT 06098

      Last Sold Summary

      • 3% Below List Price
      • $205/SF
      • 168 Days On Market
      • Last Sold Price $320,000
      • May 14, 2024

      Last Listing Agent Barry Mackiewicz A-Gold Action Realty

  • /9

    $850,000

    $149K PRICE DROP
    • Land
    • 116.5 Acres
    • $7,296 per Acre

    82 Riverton Rd, Colebrook, CT 06021

    Escape to Your Own 116 acres of Paradise in Colebrook, CT! Discover 116 +/- acres of picturesque land nestled along Riverton Road in the heart of scenic Colebrook, Connecticut. This extraordinary property offers a rare opportunity to own a vast expanse of rural beauty, complete with two serene ponds, winding old logging roads, and a mix of standing hardwoods and softwoods that create a lush,

    Suzie Larson Turning Point Realty, LLC

    82 Riverton Rd, Colebrook, CT 06021
  • 323 E Wakefield Blvd, Winsted, CT 06098

    $397,000

    Sold Jun 04, 2025

    323 E Wakefield Blvd, Winsted, CT 06098

    • 3 Beds
    • 2.5 Baths
    • 1,426 Sq Ft
    • Built 1989

    Last Sold Summary

    • 6% Above List Price
    • $278/SF
    • 4 Days On Market

    Current Estimated Value $398,303

    Last Listing Agent Heather Crabtree RE/MAX RISE

    323 E Wakefield Blvd, Winsted, CT 06098
    • 173 Smith Hill Rd, Winsted, CT 06098

      Est $375,833

      Not Listed For Sale

      173 Smith Hill Rd, Winsted, CT 06098

      • 4 Beds
      • 2 Baths
      • 1,702 Sq Ft
      • Built 1950
      173 Smith Hill Rd, Winsted, CT 06098

      Last Sold Summary

      • 5% Below List Price
      • $232/SF
      • 26 Days On Market
      • Last Sold Price $395,000
      • Dec 03, 2024

      Last Listing Agent Kim Trumbull William Raveis Real Estate

  • /35

    $345,000

    • 5 Beds
    • 3 Baths
    • 2,602 Sq Ft

    63 Meadow St, Winsted, CT 06098

    Discover 63 Meadow, a turnkey 3-unit asset where thoughtful updates, strong rental performance, and a prime location come together to prove a high confidence investment opportunity. The property offers three well-proportioned units, a two-car attached garage, off-street parking spaces, and shared outdoor area that tenants appreciate. The current owner continued to elevate the building's value and

    Lauren Hill Mark Tavares Realty, LLC

    63 Meadow St, Winsted, CT 06098
  • 150 Meadow St, Winsted, CT 06098

    $250,000

    Sold May 30, 2025

    150 Meadow St, Winsted, CT 06098

    • 4 Beds
    • 2 Baths
    • 2,094 Sq Ft
    • Built 1860

    Last Sold Summary

    • $119/SF
    • 80 Days On Market

    Current Estimated Value $261,598

    Last Listing Agent David Sartirana Northwest CT Realty

    150 Meadow St, Winsted, CT 06098
    • 123 Skinner Rd, Winsted, CT 06098

      Est $428,188

      Not Listed For Sale

      123 Skinner Rd, Winsted, CT 06098

      • 3 Beds
      • 3 Baths
      • 2,184 Sq Ft
      • Built 2005
      123 Skinner Rd, Winsted, CT 06098

      Last Sold Summary

      • 15% Above List Price
      • $170/SF
      • 82 Days On Market
      • Last Sold Price $372,000
      • Feb 21, 2024

      Last Listing Agent Jacqueline Gardner Coldwell Banker Realty

  • /38

    $749,000

    $20K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,265 Sq Ft

    121 W Wakefield Blvd, Winsted, CT 06098

    Discover unparalleled Highland Lake living with this exceptional 1.00-acre retreat, boasting 50 feet of direct lake frontage and a newly renovated dock/deck. Enjoy breathtaking water views from your sunroom, dining room, and multiple bedrooms within this versatile 4/5 bedroom home. A unique first-floor suite with a separate exterior entrance offers ideal flexibility as a main-floor master or

    Elizabeth Stockwell Coldwell Banker Realty

    121 W Wakefield Blvd, Winsted, CT 06098
  • 160 Walnut St, Winsted, CT 06098

    $320,000

    Sold Oct 21, 2025

    160 Walnut St, Winsted, CT 06098

    • 3 Beds
    • 1.5 Baths
    • 1,674 Sq Ft
    • Built 1950

    Last Sold Summary

    • 11% Above List Price
    • $191/SF
    • 11 Days On Market

    Current Estimated Value $317,384

    Last Listing Agent Jeremy Beamer William Raveis Real Estate

    160 Walnut St, Winsted, CT 06098

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