15

Winsted, CT Houses for Sale

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  • /38

    $1,295,000

    • 3 Beds
    • 3 Baths
    • 2,420 Sq Ft

    722 Lake Dr, Winsted, CT 06098

    Welcome to lake living at its finest! Built in 2014 and first time on the market. Impeccably maintained, this stunning three bedroom, 3 bath home on Highland Lake, Winchester offers the perfect blend of comfort, style, and breathtaking VIEWS! From the moment you enter you will be captivated by the open-concept design, high-end finishes and panoramic lake views from both inside and out. Enjoy

    Joanne Donne The Washington Agency

    722 Lake Dr, Winsted, CT 06098
  • /39

    $779,900

    • 3 Beds
    • 3.5 Baths
    • 4,953 Sq Ft

    111 South Rd, Winsted, CT 06098

    Perched up higher than the rest with sweeping views up a private driveway in beautiful Winchester Center you'll find this custom built 4,953 sq ft Colonial nestled in on 3.97 serene & bucolic acres. For the car enthusiasts, you'll see a 3 bay garage that can fit up to at least 7 cars if lifts are installed including a bonus 2 car tandem garage within the 3 bays. Plenty of room for oversized

    Dawn Rousseau Showcase Realty, Inc.

    111 South Rd, Winsted, CT 06098
  • /39

    $995,000

    • 4 Beds
    • 2 Baths
    • 3,088 Sq Ft

    469 Platt Hill Rd, Winsted, CT 06098

    HOME-LAND -BARN. A TRUE NEW ENGLAND CLASSIC PROPERTY IN A POST CARD SETTING! For the Discerning Customer, whether You're an ANTIQUARIAN, HORSE & ANIMAL LOVER, or just seeking for a PEACEFUL & TRANQUIL LOCATION, this LITCHFIELD COUNTY HOME could possibly fit your Criteria. Stately 1789 11 Room 3,088 Sq. Ft. Colonial expresses Love, Warmth & Care. From the Solid Beams, Chestnut Wide-Board Floors,

    Marshall Cohen Cohen Agency

    469 Platt Hill Rd, Winsted, CT 06098
  • /35

    $849,900

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

    119 W Wakefield Blvd, Winsted, CT 06098

    Have you been dreaming of breathtaking lake views and a property that is truly special, unique, and turn-key? This exceptional home includes 50 feet of waterfront access with a boat dock and lift, making it a dream for lake enthusiasts! Nestled across from the tranquil First Bay, this beautifully renovated two-family home can be enjoyed as a single-family retreat or an income-generating

    Mela Veltri Case KW Legacy Partners

    119 W Wakefield Blvd, Winsted, CT 06098
  • /40

    $1,299,999

    • 8 Beds
    • 4.5 Baths
    • 5,231 Sq Ft

    435 W Wakefield Blvd, Winsted, CT 06098

    Welcome to this spectacular Highland Lake estate, offering a unique blend of luxury & tranquility. Situated on 1.51 acres of combined land, the property includes a large barn/garage capable of housing multiple cars, boats, & equipment. The main home boasts generously sized rooms w/ high ceilings, offering an open, airy feel throughout. The kitchen has been updated w/ hardwood cabinets, featuring

    Heidi Picard-Ramsay Berkshire Hathaway NE Prop.

    435 W Wakefield Blvd, Winsted, CT 06098
  • /20

    $259,900

    • 3 Beds
    • 1 Bath
    • 1,334 Sq Ft

    22 Curtice St, Winsted, CT 06098

    Step into timeless elegance with this beautifully updated colonial-style home, where classic charm meets modern convenience. Gleaming hardwood floors flow seamlessly throughout the main living areas, creating a warm and inviting atmosphere. The fully renovated kitchen is a chef's dream, featuring premium finishes, sleek countertops, and top-of-the-line appliances. Upstairs, you'll find spacious

    Terence Dominick Complete Real Estate

    22 Curtice St, Winsted, CT 06098
  • /26

    $385,000

    • 4 Beds
    • 2 Baths
    • 1,910 Sq Ft

    147 Smith Hill Rd, Winsted, CT 06098

    Tucked away on a wooded lot, this meticulously maintained Cape features 4 spacious bedrooms and a full bathroom on each floor. Enjoy watching the birds & other wildlife on the huge rear deck or enjoy the peaceful setting on the enclosed porch. They don't make them like this anymore! The grounds have been lovingly maintained. You will want to move right in.

    SHARON GILSON Northwest CT Realty

    147 Smith Hill Rd, Winsted, CT 06098
  • /5

    $229,000

    • 3 Beds
    • 1.5 Baths
    • 976 Sq Ft

    1 Hamill Dr, Winsted, CT 06098

    This 1973 raised ranch is a charming home tucked away on a peaceful cul-de-sac in the country. The home features three bedrooms, providing ample space for your family or guests. The 1.5 bathrooms are functional, with the potential for some updates to bring them up to modern standards. The living area is spacious, and with its raised ranch design, it has the potential for a finished lower level

    Nancy Bard Bard Real Estate, LLC

    1 Hamill Dr, Winsted, CT 06098
  • /19

    $287,750

    • 4 Beds
    • 1 Bath
    • 1,492 Sq Ft

    12 Cherry St, Winsted, CT 06098

    This Home is Modern day updates Meets Old World Charm...The Updated Kitchen offers granite counter tops, custom cabinetry, tile flooring, and a pantry with Washer/ dryer hookups for convenience.. You'll find a formal dining room with hardwood floors, A main level bedroom, large living room with French doors and open stair case that leads to the upstairs.. Also on the Main level you'll find a

    Sue MCGHEE The Washington Agency

    12 Cherry St, Winsted, CT 06098
  • /14

    $224,900

    • 3 Beds
    • 1 Bath
    • 980 Sq Ft

    99 Norfolk Rd, Winsted, CT 06098

    99 Norfolk Rd, Winsted CT - Opportunity Knocks! This cute 3-bedroom Cape sits proudly on 1.3 acres and is ready for its next chapter! With vinyl siding, replacement windows, and a lovely setting perched high up from the road, the bones are here-now it just needs your vision. For those seeking an investment opportunity or ready to roll up their sleeves and bring this gem back to life, this could

    Lisa McCarthy Coldwell Banker Realty

    99 Norfolk Rd, Winsted, CT 06098
  • /24

    $375,000

    • 3 Beds
    • 1.5 Baths
    • 2,160 Sq Ft

    181 Torringford St, Winsted, CT 06098

    Charming Colonial on Nearly an Acre! Discover the perfect blend of comfort and space in this 3-bedroom, 1.5-bathroom Colonial home. Situated on almost an acre of flat, usable land, the property features a brand new grand circular driveway and a detached two-car garage. The inviting exterior, with its covered front porch, welcomes you into a home ready for its next chapter. Complete with a

    Michelle Grant Coldwell Banker Premier Real Estate

    181 Torringford St, Winsted, CT 06098
  • /40

    $1,595,000

    • 5 Beds
    • 2 Baths
    • 3,693 Sq Ft

    424 E Wakefield Blvd, Winsted, CT 06098

    Stunning Lakehouse! Victorian charm! One of the earliest Highland Lake homes with extensive custom upgrades and quality renovation. A true lakefront sanctuary offering spacious living areas, extensive outdoor living areas and wide open lake views offering South and West exposure for incredible sunsets. Lakefront dock system with hydraulic boat lift, Recently renovated kitchen /dining with newer

    KAREN NEWTON William Pitt Sotheby's Int'l

    424 E Wakefield Blvd, Winsted, CT 06098
  • /35

    $475,000

    • 3 Beds
    • 3 Baths
    • 2,747 Sq Ft

    117 South Rd, Winsted, CT 06098

    Nestled in a peaceful rural setting of Winchester Center, this charming home offers a perfect blend of rustic character and modern convenience. The property is located on over 3.3 acres of land and is adjacent to a scenic pond. Inside you will find a three bedroom two bath home with an additional in law apartment with one full bath and one bedroom and its own private entrance. The home also

    Christina Niziolek William Raveis Real Estate

    117 South Rd, Winsted, CT 06098
  • /37

    $515,000

    • 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

    David Sartirana Northwest CT Realty

    55 Walnut St, Winsted, CT 06098
  • /40

    $2,199,000

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

    431 W Wakefield Blvd, Winsted, CT 06098

    This waterfront estate at 431 W. Wakefield Blvd in Winchester, CT, is not just a home but the ultimate Highland Lake lifestyle. Imagine waking up each day to stunning lake views, with endless seasonal activities awaiting just beyond your doorstep. In the summer, dive into boating, jet skiing, swimming, and fishing right from your private dock, or simply unwind along the shoreline. As winter

    Lisa Ogren Berkshire Hathaway NE Prop.

    431 W Wakefield Blvd, Winsted, CT 06098

Why Live in Winsted

Winsted, Connecticut, situated at the edge of the Berkshire Mountains, is part of the town of Winchester and home to about 7,200 residents. Known for its affordability, Winsted features a revitalized downtown with a two-mile commercial corridor offering diverse shops, eateries, and entertainment venues in historic buildings. Residents enjoy activities like antique shopping, duck pin bowling, and Go-Kart racing. Highland Lake, one of Connecticut’s largest waterways, is popular for fishing, swimming, and boating, while East End Park provides a walking path, memorials, and a bandstand. The Winsted Senior Center offers services and activities for those aged 55 and over. The city hosts the American Mural Project, a large collaborative indoor artwork, and the Soldier’s Monument and Memorial Park, a Civil War memorial. The Winchester Historical Society, in an 1813 Colonial Revival mansion, showcases Civil War memorabilia and Victorian artifacts. Housing options include detached single-family homes, apartments, and townhouses, with many properties predating 1970. Northwestern Regional School District No. 7 is highly rated, offering programs in agricultural education. Commuting is common, with residents traveling to nearby towns like Hartford and Waterbury for work. Winsted’s crime rate is 13% below the national average, indicating a safer environment compared to many areas. Although prone to flooding due to its proximity to lakes and rivers, the town has implemented measures like retaining walls and dams to mitigate risks.

Home Trends in Winsted, CT

Housing Trends

Median Sale Price
$288,000
Median Single Family Sale Price
$300,000
Average Price Per Sq Ft
$145
Number of Homes for Sale
1
Last 12 months Home Sales
5
Months of Supply
2.40
Median List Price
$250,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
122%
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