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Explore Similar Houses Within 2 Miles of Shady, NY

  • /29

    $979,000

    • 2 Beds
    • 2 Baths
    • 900 Sq Ft

    14 Old Forge Rd, Woodstock, NY 12498

    Discover the perfect blend of historic charm and modern luxury in this exquisitely renovated 1900 carriage house. This exceptionable home features 2 bedrooms and 2 bathrooms, offering a harmonious balance of classic elegance and contemporary convenience.Step into the brand new kitchen, equipped with state of the art Bosch appliances and custom cabinetry from Transformad.com, features a

    Agent Photo

    Danielle Sevier

    Compass Greater NY, LLC

    (845) 385-1496

    14 Old Forge Rd, Woodstock, NY 12498
  • /77

    $5,200,000

    • 10 Beds
    • 8 Baths
    • 7,991 Sq Ft

    16-26 Shultis Brook Rd, Bearsville, NY 12409

    Historic compound located in the iconic hamlet of Bearsville, just minutes from the Village of Woodstock. This four residence compound dates back to the mid-1700's and is believed to be the first farm in the valley as well as one of the first homes. Sprawled over 25+ acres with a pond and meandering stream, this unique property tucked away with complete privacy. The four structures include a 3+

    Agent Photo

    Amy Hawks

    Berardi Realty

    (845) 250-0616

    16-26 Shultis Brook Rd, Bearsville, NY 12409
  • /26

    $750,000 Open Sun 12PM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,334 Sq Ft

    40 Mink Hollow Rd, Willow, NY 12495

    Nestled into 2 lush acres in legendary Woodstock, NY, Kate's Lazy Cabin is a one-of-a-kind creative escape owned by iconic B-52s lead singer Kate Pierson and renowned artist Monica Coleman. This rustic offering radiates eclectic soul, bold personality, and a deep connection to creativity—just like the town it calls home.The house itself is a layered expression of vintage charm and artistic

    Agent Photo

    Diana Polack

    Compass Greater NY, LLC

    (845) 605-7386

    40 Mink Hollow Rd, Willow, NY 12495
  • /64

    $1,499,000

    • 3 Beds
    • 2.5 Baths
    • 2,066 Sq Ft

    67 Cricket Ridge, Bearsville, NY 12409

    Welcome to Cricket Ridge Tower House, a Woodstock artists' mountaintop retreat with breathtaking views and meditative sculpture gardens located 5 minutes to the Village. Surrounded by spectacular perennial gardens, there is visual interest in all seasons with a chorus of beautiful and vibrant blooms throughout the warmer months. This home was built by and has served as inspiration for the owners,

    Amy Lonas Coldwell Banker Village Green

    67 Cricket Ridge, Bearsville, NY 12409
  • /53

    $1,695,000

    • 3 Beds
    • 3.5 Baths
    • 3,072 Sq Ft

    253 Upper Byrdcliffe Rd, Woodstock, NY 12498

    Historic Byrdcliffe Estate on One of Woodstock's Most Beloved Roads.Step into a piece of Woodstock's storied past with this enchanting 1910 Arts & Crafts masterpiece, gracefully situated on nearly six bucolic acres along one of the town's most picturesque and sought-after roads.Originally owned by Jane BYRD Whitehead and Ralph RadCLIFFE Whitehead, two of the visionary founders of the

    John Kralik Compass Greater New York, LLC

    253 Upper Byrdcliffe Rd, Woodstock, NY 12498
  • /44

    $1,299,000

    • 5 Beds
    • 3 Baths
    • 3,696 Sq Ft

    3207-3209 New York 212, Bearsville, NY 12409

    Enchanting Woodstock Compound with Craftsman Home, Historic Barn & Cottage. 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 three distinct

    Michelle Bergkamp Corcoran Country Living

    3207-3209 New York 212, Bearsville, NY 12409
  • /50

    $1,375,000

    • 4 Beds
    • 4 Baths
    • 3,193 Sq Ft

    279 Cooper Lake Rd, Bearsville, NY 12409

    Nestled along one of the most enchanting, winding roads in Woodstock, this stunning contemporary ranch offers the perfect blend of modern convenience and serene country living with the bonus of a lot of extra space in the form of a lower-level accessory dwelling unit with a separate entrance; it adds two bedrooms and provides an ideal space for guests. Alternatively, it might be used as a

    Ellen Osgood Coldwell Banker Village Green

    279 Cooper Lake Rd, Bearsville, NY 12409
  • /28

    $815,000

    • 2 Beds
    • 2 Baths
    • 1,416 Sq Ft

    2318 Glasco Turnpike, Woodstock, NY 12498

    This classic 1890s farmhouse marries period charm with high-end modern amenities in a natural setting. Bordered by quiet woodlands, meadows and a bluestone wall, the house stands out as a gem. A spacious living room, flooded with natural light, flows seamlessly into a large separate dining room featuring window benches looking onto an ample side deck-perfect for morning coffee bathed in sunrise.

    Jeannine Simmons Corcoran Country Living

    2318 Glasco Turnpike, Woodstock, NY 12498
  • /48

    $1,995,000

    • 2 Beds
    • 2 Baths
    • 1,531 Sq Ft

    128 Newcut Rd, Bearsville, NY 12409

    At the end of a private road and surrounded by forever-protected land, you'll find this serene 25-acre mountaintop escape—complete with an additional contiguous 10-acre buildable lot. Build your dream, expand your vision, or simply enjoy the privacy and open space. Breathtaking views, open meadows, and total seclusion create the perfect backdrop for peaceful living. The home itself is a

    Heidi Maloney Four Seasons Sotheby's Int'l R

    128 Newcut Rd, Bearsville, NY 12409
  • /25

    $479,500

    • 3 Beds
    • 1 Bath
    • 1,164 Sq Ft

    44 Overlook Dr, Woodstock, NY 12498

    Three bedroom, one bath, 1124 ft.2 in Woodstock. Walking distance to the Bearsville theater formally owned by Bob Dylan's manager, Albert Grossman with music and restaurants. New refrigerator, new dishwasher, stove like new ( three years old). Hot water tank(3 years old) microwave, new carpet, professionally painted inside and out, living room and large multi use room (could be 4th bedroom) not

    Qizhan Yao Realmart Realty, LLC

    44 Overlook Dr, Woodstock, NY 12498
  • /38

    $889,000

    • 4 Beds
    • 3 Baths
    • 2,125 Sq Ft

    48 Cooper Hollow Ln, Bearsville, NY 12409

    Tucked away on a scenic country road just minutes from historic Woodstock, this stunning contemporary home offers the perfect balance of privacy, tranquility, and access to nature. Set on six acres in a highly desirable neighborhood, this serene retreat is surrounded by lush woods, artfully landscaped grounds, and a feeling of peace that begins the moment you arrive. With nearby hiking trails,

    Eric Amaral Coldwell Banker Village Green

    48 Cooper Hollow Ln, Bearsville, NY 12409
  • /39

    $749,000

    • 3 Beds
    • 2.5 Baths
    • 1,592 Sq Ft

    194 Wittenberg Rd, Bearsville, NY 12409

    Tucked away just three miles from the heart of Woodstock, this timeless 1845 farmhouse is a rare and soulful offering. The property is nestled on 1.8 acres of artfully landscaped gardens, all framed by dramatic rock ledges and outcroppings. At the heart of the property is the beautifully restored main home and a striking 700-square-foot heated yurt. The yurt is seamlessly integrated into the

    Leslie Foti Coldwell Banker Village Green

    194 Wittenberg Rd, Bearsville, NY 12409
  • /30

    $2,100,000

    • 9 Beds
    • 10 Baths
    • 8,452 Sq Ft

    0 Wittenberg Rd Unit 20252191, Woodstock, NY 12498

    Welcome to Happy Brooks , The much-loved compound for many years of Woodstock Festival co-founder and legendary music industry icon Michael Lang, this mythic Mt. Tremper property boasts true style, along with a creative pedigree that dates back to the 1920s. Originally built for the artist G. Adolph Anderson, the 17 acre estate features three architecturally significant & historic structures

    Nancy Felcetto Brown Harris Stevens Hudson

    0 Wittenberg Rd Unit 20252191, Woodstock, NY 12498
  • /33

    $2,100,000

    • 9 Beds
    • 10 Baths
    • 8,452 Sq Ft

    Unlisted Address

    Welcome to Happy Brooks , The much-loved compound for many years of Woodstock Festival co-founder and legendary music industry icon Michael Lang, this mythic Mt. Tremper property boasts true style, along with a creative pedigree that dates back to the 1920s. Originally built for the artist G. Adolph Anderson, the 17 acre estate features three architecturally significant & historic structures

    Nancy Felcetto Brown Harris Stevens HV LLC

    Unlisted Address
  • /49

    $799,000

    • 3 Beds
    • 2.5 Baths
    • 1,864 Sq Ft

    12 Library Ln, Woodstock, NY 12498

    Tucked along tranquil Library Lane, this classic red cottage offers a rare blend of in-town convenience and private, garden-like seclusion. Behind the home, a fully fenced backyard - shaded by mature trees and thoughtfully landscaped - frames both the primary residence and a detached guest studio with a legal short-term rental permit, creating a true village retreat that feels peaceful and tucked

    Eric Amaral Coldwell Banker Village Green

    12 Library Ln, Woodstock, NY 12498
  • /56

    $889,000

    • 4 Beds
    • 3 Baths
    • 2,125 Sq Ft

    48 Cooper Hollow Rd, Bearsville, NY 12409

    Tucked away on a scenic country road just minutes from historic Woodstock, this stunning contemporary home offers the perfect balance of privacy, tranquility, and access to nature. Set on six acres in a highly desirable neighborhood, this serene retreat is surrounded by lush woods, artfully landscaped grounds, and a feeling of peace that begins the moment you arrive. With nearby hiking trails,

    Eric Amaral Coldwell Banker Village Green

    48 Cooper Hollow Rd, Bearsville, NY 12409
  • /28

    $650,000

    • 2 Beds
    • 2 Baths
    • 1,065 Sq Ft

    196 Tinker St, Woodstock, NY 12498

    Country charm -- less than a mile from the Woodstock Village Green! A stream meanders by the massive screened porch and deck. There are also views of your own pond while you enjoy dining al fresco just outside the sliding glass kitchen door. This house transports you to a light, airy, simpler lifestyle. The kitchen opens to a gracious dining room (with a breakfast bar and additional kitchen

    Sharon Breslau BHHS HUDSON VALLEY PROP-WDST

    196 Tinker St, Woodstock, NY 12498
  • /34

    $599,000

    • 3 Beds
    • 1.5 Baths
    • 1,500 Sq Ft

    40 Lower Byrdcliffe Rd, Woodstock, NY 12498

    Nestled in Woodstock's storied Byrdcliffe district, this charming 1920's home balances original character with modern comforts. A comprehensive renovation has brought thoughtful updates throughout, including a brand-new kitchen and baths, upgraded flooring, enhanced insulation, a new roof and a new heating system. Original stained glass windows serve as artistic focal points, honoring the home's

    Sally Sprogis Four Seasons Sothebys Intl

    40 Lower Byrdcliffe Rd, Woodstock, NY 12498
  • /25

    $499,000

    • 3 Beds
    • 2 Baths
    • 1,376 Sq Ft

    58 Baker Rd, Bearsville, NY 12409

    MOTIVATED SELLER! Discover the perfect blend of comfort, creativity, and seclusion in this charming 3-bedroom, 2-bath home nestled on almost 3 acres of varied landscape—meadows, wooded areas, striking rock outcroppings, and breathtaking mountain views. Whether you’re seeking a full-time residence or a weekend escape, this property offers a unique mix of relaxation and opportunity. Step inside to

    Heather Martin United RE Hudson Valley Edge

    58 Baker Rd, Bearsville, NY 12409
  • /25

    $489,000

    • 4 Beds
    • 2 Baths
    • 1,792 Sq Ft

    3271 Route 212, Bearsville, NY 12409

    Discover the perfect blend of comfort and opportunity in this charming duplex situated near the heart of Woodstock. This legal two-family home, each unit approximately 900 square feet, offers a unique chance to live in one side while renting out the other, making it an ideal investment property or a cozy haven for extended families.As you approach the property, a separate driveway for

    Pieta Williams Halter Associates Realty

    3271 Route 212, Bearsville, NY 12409
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