Woodstock, NY Homes for Sale

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  $1,195,000

  • 4 Beds
  • 6 Baths
  • 2,980 Sq Ft

  12 Tinker St, Woodstock, NY 12498

  Prime Village Green Historic Gem in Woodstock, NY. Discover a unique opportunity to own a piece of history in the heart of Woodstock. This remarkable 1875 era property originally known as The Snyder Homestead named after its original owner, was the grandest house in town. This old style home with its distinctive Mansard roof retains its grandeur to this day. It offers the quintessential blend of

  

  Danielle Sevier

  Compass Greater NY, LLC

  (845) 436-3857

  12 Tinker St, Woodstock, NY 12498
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  /31

  $975,000

  • 4 Beds
  • 4 Baths
  • 1,811 Sq Ft

  33 Tannery Brook Rd, Woodstock, NY 12498

  Nestled in the heart of Woodstock, this beautifully transformed farmhouse, originally constructed in the 1870s, seamlessly blends historic charm with modern living. The current owners, a talented architect and interior designer, have meticulously renovated this property to enhance its original architecture while maximizing natural light and integrating the surrounding landscape. The zoning allows

  

  Danielle Sevier

  Compass Greater NY, LLC

  (845) 456-8466

  33 Tannery Brook Rd, Woodstock, NY 12498
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  $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

  

  Danielle Sevier

  Compass Greater NY, LLC

  (845) 385-1496

  14 Old Forge Rd, Woodstock, NY 12498
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  $1,150,000

  • 2 Beds
  • 2.5 Baths
  • 2,010 Sq Ft

  109 the Middle Way, Mount Tremper, NY 12457

  Tucked away on over 7 private acres off a quiet road in coveted Mount Tremper, this striking 2-bedroom, 2.5-bath contemporary offers ultimate seclusion, panoramic mountain views, and the kind of indoor-outdoor living dreams are made of. With soaring windows and a bright open-concept layout, the living room flows effortlessly into the dining area and kitchen, complete with a breakfast bar for

  

  Catherine Quintard

  Compass Greater NY, LLC

  (845) 203-8492

  109 the Middle Way, Mount Tremper, NY 12457
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  $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+

  

  Amy Hawks

  Berardi Realty

  (845) 250-0616

  16-26 Shultis Brook Rd, Bearsville, NY 12409
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  /47

  $799,000

  • 5 Beds
  • 4 Baths
  • 1,908 Sq Ft

  39 Van Wagner Rd, Willow, NY 12495

  Experience the epitome of country living with this historic farm home nestled in the heart of the Catskill Mountains. Whether you’re looking for your forever home, a weekend escape, or to start an Airbnb, this spacious home has it all! With nearly 2000 sqft of living space, this charming abode features a BRAND NEW METAL ROOF and GUTTERS, ALL NEW WINDOWS, 5 bedrooms and 3 full bathrooms, each

  Gina Nikola Keller Williams Valley Realty

  39 Van Wagner Rd, Willow, NY 12495
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  $4,999,000

  • 4 Beds
  • 4 Baths
  • 3,899 Sq Ft

  18 Striebel Rd, Woodstock, NY 12498

  Nestled in the heart of Woodstock, this extraordinary 70+ acre estate is a rare offering of artistic heritage, architectural beauty, and serene natural surroundings. Known as The Stone House on Striebel Road, this iconic bluestone compound has stood at the crossroads of music, literature, and counterculture for over a century.Built in 1914 as a country retreat, the main Stone House

  Michelle Bergkamp Corcoran Country Living

  18 Striebel Rd, Woodstock, NY 12498
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  $1,000,000

  • 3 Beds
  • 2.5 Baths
  • 2,430 Sq Ft

  220 John Joy Rd, Wood Stock, NY 12498

  Welcome to 220 John Joy Road, a meticulously maintained and thoughtfully upgraded home tucked away in the heart of Woodstock, NY. Featuring three spacious bedrooms and two and a half baths, this property combines modern amenities with timeless charm, offering a rare opportunity to live comfortably and securely in one of the Hudson Valley’s most beloved areas. Built with concrete walls for

  Donna Gray Redfin Real Estate

  220 John Joy Rd, Wood Stock, NY 12498
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  /51

  $799,000

  • 3 Beds
  • 2 Baths
  • 1,532 Sq Ft

  97 John Joy Rd, Woodstock, NY 12498

  The best of both worlds!A boho cottage paradise and a modern ADU (Accessory Dwelling Unit). Peace and tranquility and 3 miles from the center of the most famous small town in the world. Five-star dining and unique shopping opportunities.The property is situated adjacent to the Thorne Preserve - 60 acres boasting the most painted views of Overlook Mountain. The preserve is a sweeping grassland

  Benjamin Armento Coldwell Banker Village Green

  97 John Joy Rd, Woodstock, NY 12498
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  /42

  $1,244,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,088 Sq Ft

  178 Chestnut Hill Rd, Woodstock, NY 12498

  Discover the epitome of modern luxury in this brand new build, with a sleek aesthetic that seamlessly blends style and comfort. Using ecological and state of the art building practices highlighted by exceptional craftsmanship and distinctive design. Ascend an impressive switchback floating staircase to a stunning wall of windows that flood the open concept, living, kitchen, and dining area

  Richard Vizzini Corcoran Country Living

  178 Chestnut Hill Rd, Woodstock, NY 12498
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  /47

  $1,345,000

  • 3 Beds
  • 3 Baths
  • 2,327 Sq Ft

  263 California Quarry Rd, Woodstock, NY 12498

  Live above the clouds over Woodstock, the world's most famous little town. This remarkable contemporary home is just a few minutes from the bustling center of the village, in an absolutely tranquil setting! The views are breath-taking and expansive, and seen from almost every room. The Ashokan Reservoir, the entire Shawangunk Mountain Ridge (from Mohonk to Sam's Point) Ohayo Mountain, and, even

  Daniel Winn Halter Associates Realty

  263 California Quarry Rd, Woodstock, NY 12498
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  /44

  $925,000

  • 5 Beds
  • 3 Baths
  • 2,044 Sq Ft

  4868 New York 212, Willow, NY 12495

  Escape to the Catskills with this exquisitely remodeled home in Willow - where privacy, luxury, and mountain views converge on 3.6 pristine acres just minutes from the heart of Woodstock. This 5-bedroom, 3-bathroom home is a masterclass in modern design and thoughtful craftsmanship, with every detail curated for comfort, style, and effortless living. Inside, you'll find an airy open-concept

  Richard Vizzini Corcoran Country Living

  4868 New York 212, Willow, NY 12495
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  /43

  $1,450,000

  • 4 Beds
  • 5 Baths
  • 3,080 Sq Ft

  27 Old Wagon Rd, Woodstock, NY 12498

  Just a half mile from the center of Woodstock, this bucolic 3.7-acre compound offers a rare blend of architectural charm, natural beauty, and versatile living. The property includes the main house and two outbuildings, a one-bedroom cottage and a studio with an attached three-bay garage. Bedroom and bath layout described as the primary residence having three bedrooms and three full baths

  Megan Rios Berardi Realty

  27 Old Wagon Rd, Woodstock, NY 12498
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  /45

  $1,250,000

  • 3 Beds
  • 2.5 Baths
  • 3,080 Sq Ft

  11 Grogkill Rd, Willow, NY 12495

  Classic Country ''Haven'' — it's HEAVEN really! Elegance that checks off every box! This timeless and enduring style home designed with graciously proportioned rooms with high ceilings and light streaming through windows from every direction. Centrally located and perched on 3 exclusive landscaped acres with a pool, an oversized 2-car garage, and mountain views; all next door to your own country

  Sharon Breslau BHHS Hudson Valley Properties

  11 Grogkill Rd, Willow, NY 12495
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  $1,250,000

  • 3 Beds
  • 2.5 Baths
  • 3,080 Sq Ft

  11 Grog Kill Rd, Willow, NY 12495

  Classic Country ''Haven'' — it's HEAVEN really! Elegance that checks off every box! This timeless and enduring style home designed with graciously proportioned rooms with high (12') ceilings and light streaming through windows from every direction. Centrally located and perched on 3 exclusive landscaped acres with a pool, an oversized 2-car garage, and mountain views; all next door to your own

  Sharon Breslau BHHS HUDSON VALLEY PROP-WDST

  11 Grog Kill Rd, Willow, NY 12495
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  $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
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  $1,100,000

  • 2 Beds
  • 2 Baths
  • 2,209 Sq Ft

  11 Louie Way, Woodstock, NY 12498

  A spectacular view of Bass Meadow and mountains is just one of the highpoints of this beautiful Cape Cod home on 6.1 acres located a few miles from Woodstock Village. From the home's wraparound stone patio and large windows, imagine looking out at a serene 70-acre vista of meadow and woods that is protected from development. This lovely, turnkey 2209-square-foot home features an open-plan living

  Gary Heckelman Halter Associates Realty Inc

  11 Louie Way, Woodstock, NY 12498
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  /31

  $1,099,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,252 Sq Ft

  32 Maurizi Ln, Woodstock, NY 12498

  Blending classic country charm with modern sophistication, this newly built modern farmhouse offers over 3,000 square feet of beautifully finished living space. Designed with clean lines, a neutral palette, and layered textures, it delivers a timeless aesthetic full of warmth and character. The home features four spacious bedrooms, three and a half baths, a fully finished lower level, and

  Richard Vizzini Corcoran Country Living

  32 Maurizi Ln, Woodstock, NY 12498
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  /20

  $329,000

  • 2 Beds
  • 2 Baths
  • 1,177 Sq Ft

  57 Overlook Dr, Woodstock, NY 12498

  Charming Woodstock Ranch Just Minutes from TownLocated in a quiet neighborhood just outside the center of Woodstock, this adorable single-level ranch offers easy living in a prime location. The home features a spacious living area with vaulted ceilings, new flooring, and a propane fireplace flanked by custom built-ins that add character and function.Two generously sized bedrooms open to a

  Laurie Ylvisaker Coldwell Banker Village Green

  57 Overlook Dr, Woodstock, NY 12498
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  $729,000 Open Sat 11AM - 1PM

  • 2 Beds
  • 2 Baths
  • 1,565 Sq Ft

  28 Pine Grove St, Woodstock, NY 12498

  Nestled in the heart of the Village of Woodstock, this enchanting cottage awaits your arrival. Just a block from exquisite restaurants and vibrant shopping, it graces an oversized corner lot, providing a sense of space in its beautifully landscaped, fully fenced yard.With two generous bedrooms and two full bathrooms, the home invites you into an extended living area that radiates warmth

  Sheena Lepez Compass Greater New York, LLC

  28 Pine Grove St, Woodstock, NY 12498
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  $2,950,000

  • 3 Beds
  • 3 Baths
  • 2,608 Sq Ft

  235 California Quarry Rd, Woodstock, NY 12498

  Architect-Designed Modern Retreat with Unparalleled Views Over WoodstockPerched high above the town of Woodstock, this rare and exceptional home offers a front-row seat to breathtaking panoramic views that stretch from the mountains to the Ashokan Reservoir. Designed by noted architect Les Walker, this contemporary residence evokes the magic of living in a luxurious treehouse—where every

  Ellen Osgood Coldwell Banker Village Green

  235 California Quarry Rd, Woodstock, NY 12498
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  /12

  $1,168,250

  • Land
  • 38 Acres
  • $31,054 per Acre

  33 Mamoud Hills Rd, Woodstock, NY 12401

  The Grand Estate at Mamoud HillsA Singular Offering of 37.62 Private Acres in the Catskills' Most Prestigious Hidden EnclaveLegacy has a location. This is it.Now offered as a complete estate assemblage, this extraordinary 37.62-acre landholding within the exclusive Mamoud Hills enclave is a rare opportunity in the heart of the Catskills. Comprising several contiguous,

  Cameron Ashkarkhizani Serhant LLC

  33 Mamoud Hills Rd, Woodstock, NY 12401
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  /8

  $277,550

  • Land
  • 8 Acres
  • $35,000 per Acre

  39 Mamoud Hills Rd, Kingston, NY 12401

  39 Mamoud Hills: The Art of Arrival7.93 Acres of Prepared, Private, and Inspired Land in the Catskills' Most Exclusive EnclaveDesign the life. Shape the land. Set the tone.At 39 Mamoud Hills, you are not simply buying 7.93 acres you're claiming your own corner of one of the Catskills' most prestigious private communities, just minutes from Woodstock. This is land that doesn't

  Cameron Ashkarkhizani Serhant LLC

  39 Mamoud Hills Rd, Kingston, NY 12401
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  $364,800

  • Land
  • 12 Acres
  • $30,000 per Acre

  40 Mamoud Hills Rd, Kingston, NY 12401

  Mamoud Hills: The Best-Kept Secret in the Catskills12.16 Acres of Elevated Potential in a Private Estate Community Minutes from WoodstockNot just land. Legacy.Tucked behind a gated, lamp-lit private road in the Catskills' most exclusive hideaway, this 12.16 acre estate parcel in Mamoud Hills is where architectural daydreams grow up and get built.Imagine: a long, tree-lined

  Cameron Ashkarkhizani Serhant LLC

  40 Mamoud Hills Rd, Kingston, NY 12401
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  $269,700

  • Land
  • 9 Acres
  • $30,000 per Acre

  41 Mamoud Hills Rd, Kingston, NY 12401

  Your Private Sanctuary in the Catskills' Elite Mamoud HillsDiscover a once-in-a-generation opportunity in the prestigious Mamoud Hills enclave, nestled in the luxury real estate market of the Catskills. Demonstrating the pinnacle of bespoke development potential, this over 8-acre parcel is woven into a secure private community just minutes from Woodstock, the ultimate destination for

  Cameron Ashkarkhizani Serhant LLC

  41 Mamoud Hills Rd, Kingston, NY 12401
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  /11

  $256,200

  • Land
  • 9 Acres
  • $30,000 per Acre

  21 Mamoud Hills Rd, Kingston, NY 12401

  Welcome to The Place Where Masterpieces Take Shape Tucked away in the serene embrace of the Catskills, this expansive parcel in the sought-after Mamoud Hills enclave offers more than just land—it offers a legacy. Set within a refined private community just minutes from the iconic hamlet of Woodstock, this over 8-acre homesite lies at the gateway to inspiration.A graceful

  Cameron Ashkarkhizani Serhant LLC

  21 Mamoud Hills Rd, Kingston, NY 12401
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  $1,900,000

  • 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
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  $525,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  296 Maverick Rd, Woodstock, NY 12498

  OPEN HOUSE!!! Saturday, 8/2 from 1:00-3:00.This private and beautifully sited Woodstock home is set well off the road yet convenient to everything Woodstock and the Hudson Valley have to offer. The sunshine filled living room opens up to a dining area and kitchen plus 3 bedrooms and 1.5 baths all on the main level. A fully finished walk-out lower level offers flexible space with a rec room,

  Amy Lonas Coldwell Banker Village Green

  296 Maverick Rd, Woodstock, NY 12498
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  /38

  $649,000

  • 3 Beds
  • 2 Baths
  • 1,684 Sq Ft

  92 Erikas Walk, Mount Tremper, NY 12457

  Welcome to Erika's Walk, an alluring retreat with seasonal mountain views in Mt. Tremper, just minutes from Woodstock and Phoenicia. Set on 5.32 acres with no neighbors in view, this unique home offers a peaceful Catskills escape with the perfect mix of privacy, charm, and light-filled living. With 1,684 square feet of living space, three bedrooms, and two full baths, the home is thoughtfully

  Leslie Foti Coldwell Banker Village Green

  92 Erikas Walk, Mount Tremper, NY 12457
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  $525,000

  • 4 Beds
  • 2 Baths
  • 1,652 Sq Ft

  1502 Sawkill Rd, Kingston, NY 12401

  Nestled between the vibrant arts community of Woodstock and the historic charm of Kingston, this unique 2.13-acre property offers a rare opportunity to create your own riverside sanctuary along the serene Saw Kill Creek. The main residence is a 1,073-square-foot home featuring two bedrooms and one full bathroom. Oversized windows in the living room provide stunning views of the creek, allowing

  Savannah Miceli Century 21 Alliance-NP

  1502 Sawkill Rd, Kingston, NY 12401
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  $720,000

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft

  273 Grog Kill Rd, Willow, NY 12495

  Once in a while a listing comes along that offers buyers a unique opportunity for peaceful living with luxury finishes... At 273 Grog Kill Road, you have an opportunity to treat your home like a getaway experience. The design of this contemporary home blends with tranquil scenery. As you pull in the driveway, you are provided a detached one car garage, with additional driveway parking. Enjoy

  Jorge Lugo Real Broker NY LLC

  273 Grog Kill Rd, Willow, NY 12495
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  $825,000

  • 2 Beds
  • 1 Bath
  • 1,256 Sq Ft

  90 Aarons Way, Mount Tremper, NY 12457

  Tucked away at the end of a quiet private road near the top of Roundtop Mountain, this 2-bedroom, 1-bath home offers serene seclusion surrounded by protected DEP land and a private forest preserve. A true nature lover's paradise, the property is alive with wildlife and boasts beautifully landscaped grounds, seasonal mountain views, and the potential for year-round vistas with the clearing of

  Darlene Griffin Halter Associates Realty

  90 Aarons Way, Mount Tremper, NY 12457
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  /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
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  $990,000

  • 5 Beds
  • 4 Baths
  • 2,426 Sq Ft

  8 Pine Grove St, Woodstock, NY 12498

  Discover a rare investment opportunity in the vibrant enclave of Woodstock, NY with this impeccably restored, easy-to-show 1920s farmhouse located just minutes from the bus to NYC and Woodstock's iconic dining, shops, galleries, and live music. Freshly painted, with a new roof, this proven income-generating property offers reclaimed wide-plank pine floors, exposed beams, and curated designer

  Gary Heckelman Halter Associates Realty

  8 Pine Grove St, Woodstock, NY 12498
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  /41

  $749,000

  • 2 Beds
  • 2 Baths
  • 1,208 Sq Ft

  18 Country Club Ln, Woodstock, NY 12498

  Stunning reimagined Ranch, just 1/2 Mile from the Center of Woodstock, 2/10 of a Mile to the NYC Bus Route,yet providing an excellent sense of privacy, and a perfect rural setting.Beautifully, and thoughtfully updated baths and kitchen, embracing the best of Modern Design principals and practicality.The perfect country escape, yet within easy access to restaurants, shopping and

  Margo Obourn Win Morrison Realty - W

  18 Country Club Ln, Woodstock, NY 12498
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  /35

  $749,000

  • 2 Beds
  • 2 Baths
  • 1,868 Sq Ft

  1637 Glasco Turnpike, Woodstock, NY 12498

  Welcome to the Woodstock Retreat House.This exceptional multi-residential compound has been thoughtfully renovated to the highest standards and is fully furnished with a curated mix of vintage and contemporary pieces. A proven high-volume income producer, the property offers flexibility as a primary residence, part-time escape, or short-term rental investment.Set on 1.5 lush,

  Leslie Foti Coldwell Banker Village Green

  1637 Glasco Turnpike, Woodstock, NY 12498
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  /49

  $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

  Gary DiMauro Four Seasons Sotheby's Int'l-K

  128 Newcut Rd, Bearsville, NY 12409
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  /31

  $749,900

  • 4 Beds
  • 2.5 Baths
  • 2,657 Sq Ft

  49 Dorns Wood Rd, Woodstock, NY 12498

  Nestled on 10.6 private acres at the end of a quiet cul-de-sac, this custom-built contemporary home offers a rare blend of privacy, space, and modern comfort, highlighted by charming Arts & Crafts details. This spacious 4-bedroom, 2.5-bath home features stunning handcrafted cherry woodwork in the kitchen and stairway, beautifully complemented by gorgeous hardwood floors throughout. A skylit foyer

  Megan Rios Berardi Realty

  49 Dorns Wood Rd, Woodstock, NY 12498
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  /25

  $499,500

  • 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
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  /38

  $899,000

  • 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

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