5,132

Winchester, CT Homes

Section Image
  • 00 Ramsgate Ln, Barkhamsted, CT 06063
    00 Ramsgate Ln, Barkhamsted, CT 06063
    /2

    $299,899

    • 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
  • 128 Danbury Quarter Rd, Winsted, CT 06098

    $320,000

    Sold Sep 30, 2025

    128 Danbury Quarter Rd, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1965

    Last Sold Summary

    • 8% Above List Price
    • $333/SF
    • 34 Days On Market

    Current Estimated Value $317,097

    Last Listing Agent Kim Trumbull William Raveis Real Estate

    128 Danbury Quarter Rd, Winsted, CT 06098
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /26

    $239,000

    • 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
  • 14 Pratt St, Winsted, CT 06098

    $167,900

    Sold Nov 14, 2025

    14 Pratt St, Winsted, CT 06098

    • 3 Beds
    • 1.5 Baths
    • 1,340 Sq Ft
    • Built 1900

    Last Sold Summary

    • 16% Below List Price
    • $125/SF
    • 24 Days On Market

    Last Listing Agent Amy Sartirana Northwest CT Realty

    14 Pratt St, Winsted, CT 06098
  • 107 Roberts Ave, Winsted, CT 06098
    107 Roberts Ave, Winsted, CT 06098
    107 Roberts Ave, Winsted, CT 06098
    /19

    $349,000

    Under Contract
    • 3 Beds
    • 1.5 Baths
    • 1,888 Sq Ft

    107 Roberts Ave, Winsted, CT 06098

    Peaceful country living with unlimited potential! Nestled on a quiet Winsted street, this three bedroom, two bathroom ranch sits on nearly 2 acres of private, setback land. It offers excellant structural bones and a functonal layout, making it an ideal candidate for a rewarding renovation project. The large living and dining space features high cathedral ceilings and exposed wood beams with the

    Mary Anne Casey D. Beckley Realty

    107 Roberts Ave, Winsted, CT 06098
  • 1 Hamill Dr, Winsted, CT 06098

    $340,000

    Sold Jun 02, 2026

    1 Hamill Dr, Winsted, CT 06098

    • 3 Beds
    • 1.5 Baths
    • 1,600 Sq Ft
    • Built 1973

    Last Sold Summary

    • 6% Below List Price
    • $212/SF
    • 50 Days On Market

    Current Estimated Value $342,003

    Last Listing Agent Paul Duh Realty ONE Group Connect

    1 Hamill Dr, Winsted, CT 06098
  • 217 Walnut St, Winsted, CT 06098
    217 Walnut St, Winsted, CT 06098
    217 Walnut St, Winsted, CT 06098
    /34

    $399,000

    Pending
    • 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
  • 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 $36,877

    Last Listing Agent Austin Brochu Sullivan Real Estate Inc

    256 Colebrook Rd, Winchester Center, CT 06098
  • 57 Main St, Winsted, CT 06098
    57 Main St, Winsted, CT 06098
    57 Main St, Winsted, CT 06098
    /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
  • 9 Colony Dr, Winsted, CT 06098

    $350,000

    Sold May 22, 2026

    9 Colony Dr, Winsted, CT 06098

    • 3 Beds
    • 2 Baths
    • 1,582 Sq Ft
    • Built 1966

    Last Sold Summary

    • 6% Above List Price
    • $221/SF
    • 27 Days On Market

    Current Estimated Value $328,189

    Last Listing Agent David Sartirana Northwest CT Realty

    9 Colony Dr, Winsted, CT 06098
  • 118 Meadow St, Winsted, CT 06098
    118 Meadow St, Winsted, CT 06098
    118 Meadow St, Winsted, CT 06098
    /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
  • 69 Prospect St, Winsted, CT 06098

    $274,900

    Sold Jun 29, 2026

    69 Prospect St, Winsted, CT 06098

    • 7 Beds
    • 3 Baths
    • 2,204 Sq Ft
    • Built 1900

    Last Sold Summary

    • $125/SF
    • 5 Days On Market

    Current Estimated Value $269,851

    Last Listing Agent Adam Cannon Coldwell Banker Realty

    69 Prospect St, Winsted, CT 06098
  • 147 E Wakefield Blvd, Winsted, CT 06098
    147 E Wakefield Blvd, Winsted, CT 06098
    147 E Wakefield Blvd, Winsted, CT 06098
    /29

    $279,900

    $20K PRICE DROP
    • 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
  • 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 $456,276

    Last Listing Agent David Sartirana Northwest CT Realty

    819 E Wakefield Blvd, Winsted, CT 06098
    • 36 S Main St, Winsted, CT 06098

      Est $237,488

      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

      • 73 Days On Market

  • 184 Smith Hill Rd, Winsted, CT 06098
    184 Smith Hill Rd, Winsted, CT 06098
    184 Smith Hill Rd, Winsted, CT 06098
    /37

    $765,000

    Under Contract
    • 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
  • 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 $189,543

    Last Listing Agent Ron Rudek Connecticut Realty, LLC

    111 Torringford St Unit 25, Winsted, CT 06098
  • 431 W Wakefield Blvd, Winsted, CT 06098
    431 W Wakefield Blvd, Winsted, CT 06098
    431 W Wakefield Blvd, Winsted, CT 06098
    /37

    $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
  • 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 $244,969

    Last Listing Agent Nicole Araujo Trend 2000 Real Estate

    210 Walnut St, Winsted, CT 06098
  • 132 E Lake St, Winsted, CT 06098
    132 E Lake St, Winsted, CT 06098
    132 E Lake St, Winsted, CT 06098
    /36

    $399,900

    • 3 Beds
    • 2 Baths
    • 1,820 Sq Ft

    132 E Lake St, Winsted, CT 06098

    Welcome to East Lake Street at Highland Lake, where privacy, comfort, and year-round recreation come together. Set back from the road on a private lot in the desirable First Bay area, this well-maintained 2-story home offers peaceful surroundings, refreshing breezes, and glimpses of Highland Lake through the trees from the front porch and sun-room. Offering 1,820 square feet of living space, this

    Bryan Palladino Showcase Realty, Inc.

    132 E Lake 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 $189,244

    Last Listing Agent Lisa McCarthy Coldwell Banker Realty

    99 Norfolk Rd, Winsted, CT 06098
    • 9 Fruit St, Winsted, CT 06098

      Est $232,503

      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

      • 35 Days On Market

  • 293 Torringford St, Winsted, CT 06098
    293 Torringford St, Winsted, CT 06098
    293 Torringford St, Winsted, CT 06098
    /40

    $495,000

    • 4 Beds
    • 2.5 Baths
    • 3,834 Sq Ft

    293 Torringford St, Winsted, CT 06098

    Unique opportunity to own this spacious 4-bedroom Colonial set on 27 acres in Winchester, CT. Previously home to animals, this property offers endless possibilities for hobby farming, equestrian pursuits, recreation, or simply enjoying the privacy and beauty of the countryside. Ideally located directly across the street from Green Woods Country Club, you'll enjoy convenient access to golf, and

    Shawna Mucherino Coldwell Banker Realty

    293 Torringford 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 $403,380

    Last Listing Agent David Sartirana Northwest CT Realty

    35 Glendale Ave, Winsted, CT 06098
  • 367-C&D Colebrook River Rd, Colebrook, CT 06021
    367-C&D Colebrook River Rd, Colebrook, CT 06021
    367-C&D Colebrook River Rd, Colebrook, CT 06021
    /40

    $300,000

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

    367-C&D Colebrook River Rd, Colebrook, CT 06021

    Rare opportunities like this don't come along often! Nestled on 14.3 scenic acres in the heart of beautiful Colebrook, this unique two-family property offers the perfect blend of privacy, income potential, and country living. Whether you're looking for an owner-occupied investment, multi-generational living arrangement, or a property with room to grow, this one checks all the boxes. Each unit

    Danielle Dube RE/MAX Right Choice

    367-C&D Colebrook River Rd, Colebrook, CT 06021
  • 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 $1,527,498

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

    538 Wheelers Point, Winsted, CT 06098
  • 150 Oak St, Winsted, CT 06098
    150 Oak St, Winsted, CT 06098
    150 Oak St, Winsted, CT 06098
    /19

    $549,000

    $30K PRICE DROP
    • 11 Beds
    • 5.5 Baths
    • 5,233 Sq Ft

    150 Oak St, Winsted, CT 06098

    *PRICE REDUCTION* 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 3-4 bedroom, 1 1/2 bath

    Pamela Silvestri Turning Point Realty, LLC

    150 Oak St, 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 $233,926

    Last Listing Agent David D'Amore Northwest CT Realty

    130 Stanton Ave, Winsted, CT 06098

Showing Results 161 - 200, Page 5 of 18

Connecticut Litchfield County Winchester

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group