10

Winchester, CT Houses for Sale

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  • 55 Walnut St, Winsted, CT 06098
    55 Walnut St, Winsted, CT 06098
    55 Walnut St, Winsted, CT 06098
    /37

    $469,000

    • 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

    (860) 390-5071

    55 Walnut St, Winsted, CT 06098
  • 621 Wynne Rd, Winsted, CT 06098
    621 Wynne Rd, Winsted, CT 06098
    621 Wynne Rd, Winsted, CT 06098
    /35

    $339,900

    • 2 Beds
    • 1 Bath
    • 975 Sq Ft

    621 Wynne Rd, Winsted, CT 06098

    Tucked away on a private road in the sought-after Highland Lake district, this impeccably maintained Ranch offers the perfect blend of privacy, simplicity, and natural beauty. Built in 1995 and set on a .59-acre lot, the home is surrounded by over 500 acres of preserved land, creating a peaceful, nature-filled setting that is increasingly hard to find. Inside, the home features 975 square feet of

    Agent Photo

    David Sartirana

    Northwest CT Realty

    (860) 385-6622

    621 Wynne Rd, Winsted, CT 06098
  • 1 Hamill Dr, Winsted, CT 06098
    1 Hamill Dr, Winsted, CT 06098
    1 Hamill Dr, Winsted, CT 06098
    /29

    $359,900

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

    1 Hamill Dr, Winsted, CT 06098

    Step into luxury in this nicely updated 3-bedroom raised ranch, perfectly positioned on a quiet cul-de-sac. The interior shines with hardwood floors and a designer kitchen boasting new custom cabinetry, quartz countertops and stainless-steel appliances. Lower level is completely finished featuring a large family room with natural gas stove. Enjoy maintenance-free living with a newer roof (less

    Paul Duh Realty ONE Group Connect

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

    $349,900

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

    $360,000

    • 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
  • 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
  • 431 W Wakefield Blvd, Winsted, CT 06098
    431 W Wakefield Blvd, Winsted, CT 06098
    431 W Wakefield Blvd, Winsted, CT 06098
    /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
  • 123 Old North Rd, Winsted, CT 06098
    123 Old North Rd, Winsted, CT 06098
    123 Old North Rd, Winsted, CT 06098
    /28

    $425,000 Coming Soon

    • 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
  • 121 W Wakefield Blvd, Winsted, CT 06098
    121 W Wakefield Blvd, Winsted, CT 06098
    121 W Wakefield Blvd, Winsted, CT 06098
    /38

    $769,000 Coming Soon

    • 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
Connecticut Litchfield County Winchester

Houses for Sale in Winchester, CT

Why Live in Winchester

Winchester, located in the Litchfield Hills of Connecticut, is known for its rural charm and scenic mountain views. This town, often referred to as the Gateway to the Berkshire Mountains, offers a variety of outdoor recreational activities. Highland Lake, a popular attraction, features two public beaches, a boat launch, and a marina with boat rentals and seasonal slips. Winchester Lake and Park Pond provide quieter spots for boating and freshwater fishing. Platt Hill State Park offers unmarked nature trails for hikers and birdwatchers, while nearby Burr Pond, Sunnybrook, and Stillwater Pond State Parks are within 5 miles. The Sue Grossmann Still River Greenway provides a paved path for walking, running, and biking. Green Woods Country Club boasts one of the only three 10-hole golf courses in the United States. Winsted, the downtown area of Winchester, has a walkable Main Street with shops, eateries, and creative spaces like Whiting Mills and the American Mural Project. The Gilbert School, a private secondary school functioning as the public middle and high school, is highly rated and offers various sports programs. Housing options in Winchester range from historic New England-style farmhouses and saltbox homes to Cape Cod and raised ranch-style homes in Winsted, with lakefront properties being more expensive. Winchester is car-dependent, with limited public transportation, but U.S. Route 44 and state Route 8 provide access to Torrington, Hartford, and Bradley International Airport, which is 29 miles away.

Learn more about living in Winchester

Home Trends in Winchester, CT

On average, homes in Winchester, CT sell after 50 days on the market compared to the national average of 55 days. The median sale price for homes in Winchester, CT over the last 12 months is $345,000, down 10% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$345,000
Median Single Family Sale Price
$345,000
Average Price Per Sq Ft
$248
Number of Homes for Sale
0
Last 12 months Home Sales
4
Months of Supply
0.00
Median List Price
$349,900
Median Change From 1st List Price
-2%
Median Home Sale Price YoY Change
-10%
How to Buy a Home How to Finance a Home How to Sell a Home

In Winchester, there are currently 10 houses for sale, offering an array of options for potential buyers. With houses priced between $339,900 to $1,850,000, there's a range to accomodate every budget. As of April, 2026 the median home price in Winchester is $349,900, while the average sale price is $349,687, offering insights into the local housing market. On average, houses spend 50 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Winchester, CT and find the perfect place to call home.

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