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Price Reduced Homes for Sale in Winchester, CT

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  • 122 Standard Ave, Winsted, CT 06098
    122 Standard Ave, Winsted, CT 06098
    122 Standard Ave, Winsted, CT 06098
    /16

    $389,900

    $10K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 1,944 Sq Ft

    122 Standard Ave, Winsted, CT 06098

    Welcome home to this well-maintained 4-bedroom Colonial tucked away on a quiet dead-end street. The newly renovated eat-in kitchen features updated cabinetry, countertops, and finishes, creating a great space for everyday living and gathering. The spacious living room and dining area offer plenty of room to make the home your own, while four bedrooms provide flexibility for family, guests, or a

    Agent Photo

    Amanda Balaski

    Northwest CT Realty

    122 Standard Ave, Winsted, CT 06098
  • 752 Lake Dr, Winsted, CT 06098
    752 Lake Dr, Winsted, CT 06098
    752 Lake Dr, Winsted, CT 06098
    /39

    $1,550,000

    $50K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,129 Sq Ft

    752 Lake Dr, Winsted, CT 06098

    Experience the best of lakefront living with breathtaking views, spectacular sunsets, and exceptional outdoor spaces. This amazing waterfront home features a brand-new 100' x 14' Brazilian hardwood deck, a 35' x 6' stationary Trex and steel dock, and a private cabana-perfect for relaxing, boating, swimming, and entertaining. Soak in panoramic water views from multiple vantage points, including

    Agent Photo

    Pam Famiglietti

    William Raveis Real Estate

    752 Lake Dr, Winsted, CT 06098
  • 55 Walnut St, Winsted, CT 06098
    55 Walnut St, Winsted, CT 06098
    55 Walnut St, Winsted, CT 06098
    /37

    $410,000

    $140K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 5,016 Sq Ft

    55 Walnut St, Winsted, CT 06098

    Timeless Victorian with Endless Possibilities.Step into a piece of history with this stunning Victorian property, a landmark in the community and home to The Maloney Funeral Home since the early 1900's. Nestled in the TCR Zone, this versatile building offers a wealth of potential. The TCR Zone allows for accessory residential uses, community centers, family day care homes, single-family

    Agent Photo

    David Sartirana

    Northwest CT Realty

    55 Walnut St, Winsted, CT 06098
  • 70 Walnut St, Winsted, CT 06098
    70 Walnut St, Winsted, CT 06098
    70 Walnut St, Winsted, CT 06098
    /28

    $324,900

    $45K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 2,722 Sq Ft

    70 Walnut St, Winsted, CT 06098

    Step back in time and experience the timeless elegance of this spacious 2,722 sq. ft. Victorian offering 10 rooms, 5 bedrooms, and 1.5 baths. Rich in original character and architectural detail, this classic home showcases beautiful hardwood floors, impressive natural woodwork, pocket doors, built-ins, decorative moldings, and stunning stained-glass accents that capture the craftsmanship of a

    Agent Photo

    David Sartirana

    Northwest CT Realty

    70 Walnut St, Winsted, CT 06098
  • 319 White Oak Trail, Winchester, CT 06098
    319 White Oak Trail, Winchester, CT 06098
    319 White Oak Trail, Winchester, CT 06098
    /5

    $37,900

    $32K PRICE DROP
    • Land
    • 5,227 Sq Ft
    • $315,833 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
  • 143 Holabird Ave, Winsted, CT 06098
    143 Holabird Ave, Winsted, CT 06098
    143 Holabird Ave, Winsted, CT 06098
    /28

    $595,900

    $33K PRICE DROP
    • 8 Beds
    • 4.5 Baths
    • 4,800 Sq Ft

    143 Holabird Ave, Winsted, CT 06098

    One of the finest grand classic Colonial homes where timeless charm and beautiful details can still be found throughout. Features include elegant crown molding, rich wood paneling, wide baseboard molding, gleaming hardwood floors, and a sweeping grand staircase-all adding to the warmth and character of this truly special home. This home features formal dining room, sitting room with fireplace,

    Linda Ganem Borla & Associates Real Estate

    143 Holabird Ave, Winsted, CT 06098
  • 535,538 W Wakefield Blvd, Winchester, CT 06098
    535,538 W Wakefield Blvd, Winchester, CT 06098
    535,538 W Wakefield Blvd, Winchester, CT 06098
    /6

    $525,000

    $270K PRICE DROP
    • Land
    • 10,018 Sq Ft
    • $2,282,609 per Acre

    535,538 W Wakefield Blvd, Winchester, CT 06098

    This waterfront property is ideal for contractors or individuals who want to build a year-round home on Highland Lake's West side. The property is being sold as a package (3 lots have been approved for construction, parking, and a well ). The lots consist of .10 acres across the street from the water and .023 acres on the water.

    chris marino Cohen Agency

    535,538 W Wakefield Blvd, Winchester, CT 06098
  • 14 Bank St, Winsted, CT 06098
    14 Bank St, Winsted, CT 06098
    14 Bank St, Winsted, CT 06098
    /23

    $319,900

    New Construction $20K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,034 Sq Ft

    14 Bank St, Winsted, CT 06098

    New Construction - Easy to Maintain - Open Floor Plan - Central Air - Vinyl Plank flooring throughout. White Shaker Kitchen with Island and granite countertops. All stainless steel kitchen appliances. Separate laundry room on main level. Glass paneled door to covered deck off the living room area. Two spacious bedrooms with large closets. Entry foyer with large walkin closet Large heated garage

    David White OwnerEntry.com

    14 Bank St, Winsted, CT 06098
  • 325 E Wakefield Blvd, Winsted, CT 06098
    325 E Wakefield Blvd, Winsted, CT 06098
    325 E Wakefield Blvd, Winsted, CT 06098
    /40

    $304,900

    $15K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,192 Sq Ft

    325 E Wakefield Blvd, Winsted, CT 06098

    Enjoy beautiful water views and access to Highland Lake from this inviting home offering comfortable living spaces and desirable features throughout. The main level features a galley kitchen with plentiful white cabinetry, laminate flooring, refrigerator, dishwasher, and electric range. A convenient powder room and stackable washer add functionality. The spacious living room/dining area features

    Anthony Gonsalves RE/MAX RISE

    325 E Wakefield Blvd, Winsted, CT 06098
Connecticut Litchfield County

Price Reduced Real Estate & Homes for Sale in Winchester, CT

Home Prices in Winchester, CT

The median home sale price in Winchester, CT is $370,000, up 5% year-over-year. Homes in Winchester sell in 58 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$370,000
Median Single Family Sale Price
$370,000
Median 2 Bedroom Sale Price
$370,000
Average Price Per Sq Ft
$232
Number of Homes for Sale
9
Last 12 months Home Sales
3
Months of Supply
0.00
Median List Price
$359,900
Median Change From 1st List Price
-3%
Median Home Sale Price YoY Change
5%
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