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Winsted, CT Homes for Sale with Acreage

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  • /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
  • /13

    $649,900

    • 5 Beds
    • 1.5 Baths
    • 2,304 Sq Ft

    115 Old Robertsville Rd, Winsted, CT 06098

    Development Opportunity! 41.23 Acres with Historic Home & Barn - Subdivision Possible Rare chance to own a prime 41.23-acre parcel in New England with an 1800 Antique Colonial Farmhouse and classic English/New England hybrid barn. The land may be subdividable and is located near the highly desirable Riverwalk Condominiums, making it ideal for new condo development (subject to approvals). The

    Jared Tedesco Litchfield County Real Estate

    115 Old Robertsville Rd, Winsted, CT 06098
  • /35

    $499,000

    • 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
  • /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
  • /37

    $319,900

    • 2 Beds
    • 1.5 Baths
    • 1,034 Sq Ft

    389 Colebrook River Rd, Winsted, CT 06098

    Charming Bungalow with a cozy cottage feel, beautifully updated and ready to enjoy! The main level features a warm and inviting country kitchen with breakfast bar, an open dining area with sliders leading to the rear deck, a spacious living room with access to a classic farmhouse-style front porch, and a convenient half bath. Upstairs offers two modest bedrooms, a full bath, and a small office or

    David Sartirana Northwest CT Realty

    389 Colebrook River Rd, Winsted, CT 06098
  • /14

    $234,900

    • 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
  • /8

    $175,000

    • 4 Beds
    • 2 Baths
    • 2,914 Sq Ft

    100 Norfolk Rd, Winsted, CT 06098

    Endless Potential on 3.7 acres! 4 bedroom and 2 bath cape is a single-family home that was formerly used as a small homestead farm. This home features an open floor plan with soaring 10-foot ceilings on the first floor. The layout is flexible and offers plenty of room to grow. The home is in need of a full rehab and is perfect for investors, DIY enthusiasts, or anyone ready to bring their vision

    Katie Breitkreutz Dave Jones Realty, LLC

    100 Norfolk Rd, Winsted, CT 06098
  • /28

    $380,000 Open Sun 1PM - 3PM

    • 4 Beds
    • 1 Bath
    • 1,978 Sq Ft

    279 Pratt St, Winsted, CT 06098

    Perched atop Pratt Street in Winsted, this traditional farmhouse offers a peaceful retreat on a generous 1.75-acre lot. Tucked away from the hustle and bustle, the property provides a quiet sanctuary surrounded by nature, perfect for those yearning to live out their farming dreams. The home itself features a classic farmhouse charm with inviting living spaces. You'll find warm hardwood floors

    Michelle Grant Coldwell Banker Premier Real Estate

    279 Pratt St, Winsted, CT 06098
  • /40

    $1,400,000 Open Sun 2PM - 4PM

    • 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 1.3 acres of level 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
  • /40

    $2,600,000

    • 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
  • /5

    $295,000

    • Land
    • 51 Acres
    • $5,784 per Acre

    393 Winchester Rd, Winsted, CT 06098

    WINCHESTER CREST 51 acres of forested gently rolling land sited upland in Winchester Center. There is a former homesite and multiple choices for additional homesites affording complete privacy. There is abundant wildlife, trails, intermittent streams, dense and sparse forest. Perfect for year round home site, weekend retreat or recreational land.

    Tom McGowan Elyse Harney Real Estate

    393 Winchester Rd, Winsted, CT 06098
  • /2

    $69,000

    • Land
    • 2.00 Acres
    • $34,500 per Acre

    503 N Main St, Winsted, CT 06098

    Prime Building Lot Near Downtown & Highland Lake-Discover the perfect setting for your dream home on this 2 acre lot at 503 N Main Street. The Property has over 500' of road frontage, permitted uses include; accessory residential uses, family day care home, farm, seasonal cottages, single family dwelling. The property offers a peaceful atmosphere while maintaining easy access to downtown

    Charles Albertario William Raveis Real Estate

    503 N Main St, Winsted, CT 06098
  • /2

    $749,900

    • 7 Beds
    • 3 Baths
    • 3,486 Sq Ft

    39 S Main St, Winsted, CT 06098

    THREE PROPERTIES ONE PRICE!!! Includes single family, multi family & additional lot totaling 4.36 acres. 1. 3500 sq ft 2 family home featuring 1800's architecture including massive period correct windows, wrap around porch, beautiful stone foundation, and detached 2 car garage. 5 bed, 2 1/2 bath main house with 2 bed, 1 bath attic apartment, freshly updated. Brand new whole house natural gas

    RYAN HORVAY Smith & DeGroat Real Estate

    39 S Main St, Winsted, CT 06098

Home Trends in Winsted, CT

Housing Trends

Median Sale Price
$289,450
Median Single Family Sale Price
$317,500
Median Townhouse Sale Price
$160,000
Average Price Per Sq Ft
$242
Number of Homes for Sale
10
Last 12 months Home Sales
44
Months of Supply
2.70
Median List Price
$299,949
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
16%
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