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Explore Similar Houses Within 2 Miles of Shady, NY

  • /50

    $1,699,000 Open Sat 11AM - 1PM

    • 8 Beds
    • 5.5 Baths
    • 4,648 Sq Ft

    2320 Glasco Turnpike, Woodstock, NY 12498

    Welcome to The Waterfall House, a truly rare offering nestled in the heart of Woodstock Proper, where nature, creativity, and privacy converge in the most enchanting way. Being offered for the first time, this storied 3,023 sq ft brick colonial is more than a home; it’s an experience, a retreat, and an open canvas for your vision to unfold. Set on nearly 12 acres of lush, mature landscape, the

    Leigh Wagner-Quintana Keller Williams Hudson Valley

    2320 Glasco Turnpike, Woodstock, NY 12498
  • /34

    $650,000

    • 2 Beds
    • 1 Bath
    • 1,436 Sq Ft

    117 Ohayo Mountain Rd, Woodstock, NY 12498

    Set against a backdrop of sweeping mountain views and quiet Woodstock landscape, this inviting country property offers a rare blend of charm, space, and opportunity. The main home features 2 bedrooms and 1 bath, with a warm, welcoming interior defined by original hardwood floors, rich wood-paneled walls, and a classic wood-burning fireplace that anchors the living room. A bluestone enclosed porch

    Donna Brooks Compass Greater NY, LLC

    117 Ohayo Mountain Rd, Woodstock, NY 12498
  • /29

    $1,499,900

    • 3 Beds
    • 4 Baths
    • 3,330 Sq Ft

    106 Mountain Laurel Ln, Woodstock, NY 12498

    A truly one-of-a-kind residence and rare opportunity, this exceptional home offers a seamless blend of architecture and art in the heart of Woodstock, walking distance to Tinker Street, yet set privately on 1.73 secluded acres just minutes from the village.Designed as a fusion of a Frank Lloyd Wright–inspired contemporary addition and an original Buckminster Fuller–style geodesic dome, the

    Ashley Olson Minard eXp Realty

    106 Mountain Laurel Ln, Woodstock, NY 12498
  • /70

    $3,600,000

    • 4 Beds
    • 4 Baths
    • 5,272 Sq Ft

    306 Meads Mountain Rd, Woodstock, NY 12498

    Inside Swoop House there is a versatile floor plan that includes four en suite bedrooms, one an attached guest suite, and two two-story great rooms, one of which was designed as a professional art studio. Designed by FT Architecture & Interiors and inspired by the Diller Scofidio Slow House, two non-parallel curved walls and sloping ceilings create a graceful series of shapes. This singular

    Kimberly Cantine Halter Associates Realty

    306 Meads Mountain Rd, Woodstock, NY 12498
  • /31

    $2,400,000

    • 5 Beds
    • 4.5 Baths
    • 2,978 Sq Ft

    177 Tinker St, Woodstock, NY 12498

    Fall in love with this artfully reimagined and expanded 1930 farmhouse, privately set on a gentle hill just moments from the heart of Woodstock. Rich in history and character, this special home was once owned by Michael Lang, the legendary founder of the 1969 Woodstock Festival—adding a rare and meaningful connection to the town's iconic past.Thoughtfully renovated, the home offers a

    Joan Capria Four Seasons Sotheby's Int'l R

    177 Tinker St, Woodstock, NY 12498
  • /61

    $775,000

    • 2 Beds
    • 1.5 Baths
    • 1,410 Sq Ft

    15 Lake View Dr, Lake Hill, NY 12448

    Own this stunning, architect-designed contemporary home in Woodstock, NY. Professionally decorated and thoughtfully crafted with passive solar principles, this energy-efficient residence seamlessly blends modern design with its natural surroundings. Set just across the road from the famous Cooper Lake, the home is nestled in a beautiful, 3 acre wooded setting—private yet not isolated—surrounded

    Mackenzie Grate The Machree Group, LLC

    15 Lake View Dr, Lake Hill, NY 12448
  • /72

    $1,495,000

    • 3 Beds
    • 3 Baths
    • 2,566 Sq Ft

    1 Wittenberg Rd, Bearsville, NY 12409

    Welcome to Bearsville Record House, a landmark property with a legacy deeply rooted in American music. Originally built in 1873 and once home to famed Bearsville Records, this storied compound includes two dwellings; the main farmhouse and a guest cottage, plus a studio building waiting to be finished to your specs. A gunite saltwater pool, outdoor kitchen, and fenced-in plum orchard complete the

    Jessica Brasseur Houlihan Lawrence Millbrook Of

    1 Wittenberg Rd, Bearsville, NY 12409
  • /49

    $3,500,000

    • 4 Beds
    • 4 Baths
    • 4,201 Sq Ft

    289 Upper Byrdcliffe Rd, Woodstock, NY 12498

    Set on nearly 9 serene acres in the heart of Woodstock's historic Byrdcliffe Arts Colony is a rare synthesis of architectural precision and natural harmony—an embodiment of award-winning architect John Storyk's deep understanding of space, sound, and site. Designed in 1969 at the very beginning of Storyk's now-legendary career—just after his groundbreaking work on Jimi Hendrix's Electric Lady

    Sharon Breslau BHHS HUDSON VALLEY PROP-WDST

    289 Upper Byrdcliffe Rd, Woodstock, NY 12498
  • /42

    $1,199,000

    • 4 Beds
    • 2 Baths
    • 3,378 Sq Ft

    3207-3209 New York 212, Bearsville, NY 12409

    Enchanting Woodstock Compound with a Craftsman Home, Cottage, and Historic Barn. Welcome to a truly rare offering in the heart of the Catskills, just minutes from the center of Woodstock, yet tucked away in a storybook setting of trees, meadows, and the soothing sounds of the Sawkill stream. This private 1.85-acre homestead compound blends rustic charm with modern versatility, featuring a

    Michelle Bergkamp William Pitt Sotheby's Interna

    3207-3209 New York 212, Bearsville, NY 12409
  • /103

    $6,700,000

    • 3 Beds
    • 6 Baths
    • 4,688 Sq Ft

    125 Valley View Way, Lake Hill, NY 12448

    Welcome to Nature's Edge -- a Woodstock estate, where wilderness meets luxury. Perched at the end of a secluded private road, this modern mountain marvel offers unmatched privacy, serenity, and grandeur. Surrounded by natural woodscapes and native rock outcroppings, this 40 acre property sits adjacent to over 500 acres of forever wild NYC DEP land. The home itself, a Barry Price architectural

    Heidi Rothe Grist Mill Real Estate

    125 Valley View Way, Lake Hill, NY 12448
  • /30

    $898,000

    • 2 Beds
    • 2 Baths
    • 900 Sq Ft

    14 Old Forge Rd, Woodstock, NY 12498

    PROPERTY HIGHLIGHTS. Big ''Tiny House'': Designed for people who love Small Efficient Spaces, by the Water, with Mountain Views, enjoy living ''uncarred'', in the most Central Location in Woodstock. Layout: 2 bedrooms and 2 bathrooms. Exceptionally rare Climate Resilient Construction featuring Steel floor and ceiling joists with comprehensive Energy Efficient Upgrades throughout. INTERIOR

    Danielle Sevier Compass Greater NY, LLC

    14 Old Forge Rd, Woodstock, NY 12498
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