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Craftsman Homes for Sale in Windham County VT

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  • /60

    $3,995,000

    • 4 Beds
    • 5.5 Baths
    • 5,500 Sq Ft

    816 Black Bear Rd, Jamaica, VT 05343

    Set atop the Vermont hillside with stunning views, offering 4 bedrooms with additional sleeping rooms accommodating up to 16 family and friends. A custom-built home by The Wadsworth Design Build/Vermont Barns is an example of craftsmanship blended with modern luxury. Timber-framed architecture, this four-bedroom, six-bath estate offers a warm, rustic elegance that embraces its natural

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    816 Black Bear Rd, Jamaica, VT 05343
  • /37

    $1,295,000

    $20K PRICE INCREASE
    • 5 Beds
    • 3.5 Baths
    • 3,040 Sq Ft

    4427 W Hill Rd S, Jamaica, VT 05343

    A true Vermont lodge in every sense—warm, welcoming, beautifully appointed, and designed to bring people together. This exceptional mountain retreat combines the character and comfort buyers dream about in a Vermont home with the space, amenities, and proven rental history that make it equally appealing as an investment. The property has enjoyed a strong rental history with repeat guests who

    Carrie Mathews Winhall Real Estate

    4427 W Hill Rd S, Jamaica, VT 05343
  • /46

    $457,000

    $28K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    4027 Route 100 Hwy, Wardsboro, VT 05360

    Welcome to Your Vermont Retreat on scenic Route 100 in Wardsboro. Beautifully maintained and thoughtfully designed, this turnkey 3-bedroom, 2-bath home is ready to enjoy from day one whether as your full time residence, vacation getaway, or a highly successful short-term rental that guests absolutely love. Walking in through the covered entry you’ll find soaring cathedral ceilings in the living

    Steve Goldfarb Deerfield Valley Real Estate

    4027 Route 100 Hwy, Wardsboro, VT 05360
  • /60

    $945,000

    • 2 Beds
    • 1.5 Baths
    • 2,721 Sq Ft

    51 Dusty Ridge Rd, Putney, VT 05346

    Nestled along one of Putney's most scenic country roads, this private 18.3 acre property offers the perfect balance of wooded privacy, open space, and classic Vermont charm. Stone walls, mature perennial gardens, walking trails, and a meandering stream create a peaceful setting. The thoughtfully designed home offers 2,721 square feet of living space with 2 bedrooms and 2 bathrooms. A soaring

    Keith Nowak Four Seasons Sotheby's Int'l Realty

    51 Dusty Ridge Rd, Putney, VT 05346
  • /30

    $350,000

    Open Sat 11AM - 1PM
    • 3 Beds
    • 1.5 Baths
    • 1,406 Sq Ft

    36 Pine St, Brattleboro, VT 05301

    In the heart of it all! Just minutes to everything Brattleboro...Day or night, there is something fun to do....movies, eats, hiking and so may other choices....3 generations have lived in and loved this home, gardening, sipping on the back deck, saying hello on the Vermont front porch. An era when homes were built with good bones, craftsmanship and quality hard to afford today. A pretty face to

    Christine Lewis Brattleboro Area Realty

    36 Pine St, Brattleboro, VT 05301
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