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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
  • /26

    $750,000

    • 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
  • /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
  • /51

    $1,750,000

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

    128 Newcut Rd, Bearsville, NY 12409

    Nestled atop your very own private mountaintop, this captivating retreat is the sanctuary you've been dreaming of. Enjoy 35 acres of serene woodland and breathtaking views. This residence is the ultimate escape for weekenders, outdoor enthusiasts, and creatives seeking the solitude necessary to ignite their next masterpiece.A peaceful haven with expansive mountain vistas, you'll find

    Heidi Maloney Four Seasons Sotheby's Int'l R

    128 Newcut Rd, Bearsville, NY 12409
  • /39

    $1,985,000

    • 6 Beds
    • 3 Baths
    • 3,023 Sq Ft

    2320 Glasco Turnpike, Woodstock, NY 12498

    For the first time in its history, this 12-acre family estate—designed, built, and cherished by a prominent Woodstock family—comes to market. A rare opportunity for the next generation to build their own private estate or compound, walking distance to town. Complete with babbling brook, waterfall, two vintage Woodstock cottages and acres of woods to explore. A perfect retreat! to your dream

    George Denise Keller Williams Realty HV Nort

    2320 Glasco Turnpike, Woodstock, NY 12498
  • /31

    $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 Byrdcliffe

    John Kralik Compass Greater NY, LLC

    253 Upper Byrdcliffe Rd, Woodstock, NY 12498
  • /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
  • /13

    $440,000

    • 1 Bed
    • 1 Bath
    • 841 Sq Ft

    57 Ohayo Mountain Rd, Woodstock, NY 12498

    THE EXCITEMENT AND CONVENIENCE OF WOODSTOCK VILLAGE LIVING! Adorable period bungalow moments from Tinker St. and all the dining, entertainment, shops, hiking, biking and golfing that Woodstock has to offer. This 1 BR, 1 BA charmer features an additional room/four-season sun porch, handsome masonry fireplace with river rock chimney, modern kitchen, a clawfoot tub, separate laundry area,

    Laurie Osmond BHHS HUDSON VALLEY PROP-WDST

    57 Ohayo Mountain Rd, Woodstock, NY 12498
  • /25

    $739,000

    • 4 Beds
    • 3 Baths
    • 2,208 Sq Ft

    36-38 Ohayo Mountain Rd, Woodstock, NY 12498

    Welcome to The Mill House, nestled in the vibrant heart of Woodstock, NY—a delightful farmhouse that beautifully blends historic charm with modern comforts. Spanning 1,764 square feet, this inviting home includes three cozy bedrooms and two full bathrooms, offering a spacious layout for everyday living.As you wander through the lush gardens and cross a quaint bridge over a seasonal

    Sheena Lepez Compass Greater New York, LLC

    36-38 Ohayo Mountain Rd, Woodstock, NY 12498
  • /30

    $575,000

    • 2 Beds
    • 2 Baths
    • 1,130 Sq Ft

    233 Wittenberg Rd, Bearsville, NY 12409

    Picture yourself in this charming 1940 cottage with a roaring fire in its fieldstone double-height fireplace. If that doesn't capture your heart, the open living and dining areas with birch beamed ceilings will. Large expanses of windows flood the space with light, adding more charm essential to modern living. A wonderfully convenient full bath with claw-foot tub adds to the easy

    Henry Ford Coldwell Banker Village Green

    233 Wittenberg Rd, Bearsville, NY 12409
  • /38

    $795,000

    • 3 Beds
    • 2 Baths
    • 2,390 Sq Ft

    1 Bellows Ln, Woodstock, NY 12498

    Welcome to Blues Quarry—where tucked-away tranquility meets ''close to everything'' convenience in the heart of Woodstock, NY.This 2.78-acre ridge-top retreat offers a seasonal stream below, plenty of flat usable land up top, and a landscape framed by a sweeping lawn, mature flower gardens, and wooded privacy.For the dreamers and doers: a dog kennel with fenced yard can keep its current

    Baris Demirel Serhant LLC

    1 Bellows Ln, Woodstock, NY 12498
  • /109

    $6,700,000

    • 3 Beds
    • 6 Baths
    • 2,417 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
  • /27

    $300,000

    • 3 Beds
    • 1 Bath
    • 917 Sq Ft

    20 Overlook Dr, Woodstock, NY 12498

    Woodstock Ranch with Room to Make It Your OwnJust minutes from the heart of Woodstock, this single-level ranch combines charm, comfort, and exciting potential. The sunny living room flows to a cozy back sitting area, while three freshly painted bedrooms are ready for immediate enjoyment. The living area awaits your choice of flooring, and the kitchen offers the option to open a wall for

    Baris Demirel Serhant LLC

    20 Overlook Dr, Woodstock, NY 12498
  • /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
  • /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
  • /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. PLUS, there is a legal Woodstock STR permit! Behind the home, a fully fenced backyard - shaded by mature trees and thoughtfully landscaped - frames both the primary residence and detached guest studio with its legal short-term rental permit. This is a true

    Eric Amaral Coldwell Banker Village Green

    12 Library Ln, 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
  • /28

    $575,000

    • 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
  • /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
  • /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 introduced thoughtful upgrades throughout, including a brand-new septic system, kitchen and baths, new roof, heating system, flooring, and enhanced insulation. Original stained glass windows remain as artistic focal points, honoring the

    Sally Sprogis Four Seasons Sothebys Intl

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

    $450,000

    • 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
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