Woodstock, NY Houses for Sale

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  /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

  

  Danielle Sevier

  Compass Greater NY, LLC

  (845) 385-1496

  14 Old Forge Rd, Woodstock, NY 12498
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  /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

  

  Diana Polack

  Compass Greater NY, LLC

  (845) 605-7386

  40 Mink Hollow Rd, Willow, NY 12495
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  /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+

  

  Amy Hawks

  Berardi Realty

  (845) 250-0616

  16-26 Shultis Brook Rd, Bearsville, NY 12409
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  /40

  $1,595,000 New Construction

  • 3 Beds
  • 4 Baths
  • 3,544 Sq Ft

  18 Ryan Dr, West Hurley, NY 12491

  Built in 2022, this modern home balances thoughtful design with a connection to nature. Every aspect of the home has been done with intention, including its private location nestled in the woods, energy efficient features and open, light-filled spaces. This is a rare find - a recently built home with privacy less than 15 minutes from both Woodstock and Kingston. As you approach the house

  

  Hillary Kolos

  Compass Greater NY, LLC

  (845) 534-6610

  18 Ryan Dr, West Hurley, NY 12491
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  /43

  $1,199,000 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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  /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
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  /44

  $895,000

  • 4 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

  $1,350,000

  • 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

  This property has an accepted offer. 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

  Sharon Breslau BHHS Hudson Valley Properties

  11 Grogkill Rd, Willow, NY 12495
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  /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
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  /42

  $1,495,000

  • 2 Beds
  • 4 Baths
  • 2,727 Sq Ft

  96 Meads Mountain Rd, Woodstock, NY 12498

  Tucked away on 7.26 acres of lush, storybook landscape with a stream-fed pond, this quintessential Woodstock home is more than a residence—it’s an experience. As you approach via a winding driveway that crosses a babbling stream and year-round waterfalls, the magic begins. You can hear the cascading water from the house itself, setting the tone for the serenity that follows. The main home offers

  Lisa Halter Halter Associates Realty Inc

  96 Meads Mountain Rd, Woodstock, NY 12498
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  /28

  $1,150,000

  • 3 Beds
  • 2 Baths
  • 1,948 Sq Ft

  99 Cannon Cir, Woodstock, NY 12498

  Tucked away in the pristine Ohayo Mountain forest and less than a mile from the heart of Woodstock, Cannon House offers the rare combination of seclusion, comfort, and modern design. Set on 1.65 acres, this contemporary retreat, built in 2020, is thoughtfully designed to immerse you in the natural surroundings while providing every modern convenience. With three bedrooms and two and a half baths,

  Laurie Ylvisaker Coldwell Banker Village Green

  99 Cannon Cir, Woodstock, NY 12498
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  /39

  $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

  $999,000 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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  /21

  $995,000

  • 5 Beds
  • 2 Baths
  • 2,772 Sq Ft

  1311 Wittenberg Rd, Mount Tremper, NY 12457

  Set well back from the road behind a handsome gated entry, this modern Catskills hideaway delivers the privacy everyone wants and the volume everyone hopes for. The approach is long and quiet; the house reveals itself slowly—wrapped by trees, with sky above and room to breathe on 4.04 acres. Inside, an airy great room rises with high ceilings and broad windows that pull in daylight and

  WINTON MORRISON Win Morrison Realty - W

  1311 Wittenberg Rd, Mount Tremper, NY 12457
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  /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
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  /24

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,607 Sq Ft

  311 Wittenberg Rd, Bearsville, NY 12409

  Welcome to the Stone Cottage A home that embodies the spirit of Woodstock with character, warmth and charm. Enter through the vintage kitchen, which opens into a charming dining area , the perfect setting for intimate dinners. The dining area flows seamlessly into the living room, creating the perfect gathering space for family and friends. Vaulted ceilings, wide board pine floors, a

  Anne Rajs Corcoran Country Living

  311 Wittenberg Rd, Bearsville, NY 12409
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /17

  $2,200,000

  • 8 Beds
  • 10 Baths

  20 Country Club Ln, Wood Stock, NY 12498

  A Rare Opportunity in the Heart of Woodstock. Own a remarkable piece of Woodstock history. Once the site of the Woodstock Lodgeand The Pinecrest, this storied property invites you to step back in time whileenvisioning its next chapter.Set on 6.5 acres of scenic land with a mix of cleared grounds, wooded trails, and aseasonal stream, this property offers a rare combination of

  Kathryn Johnson William Pitt Sothebys Int Rlty

  20 Country Club Ln, Wood Stock, NY 12498
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  /24

  $540,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 1.5 Baths
  • 1,804 Sq Ft

  5 Violet Place, Woodstock, NY 12498

  Lovely 3-4 bedroom home located in a quiet, friendly neighborhood, just minutes from the shopping, dining, and arts in the village of Woodstock, and about 15 minutes to bustling Kingston and Saugerties. 12 minutes to Thruway, 15 minutes to Trailways bus in Kingston (5 minutes to Woodstock stop), 25 minutes to Rhinecliff Amtrak train station for car-free access to NYC. Upstairs you'll find 3

  Fawn Denue Keller Williams Hudson Valley

  5 Violet Place, Woodstock, NY 12498
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  /62

  $649,000

  • 4 Beds
  • 2 Baths
  • 1,188 Sq Ft

  12 Arnold Dr, Woodstock, NY 12498

  Located on a quiet, country road is this meticulously maintained raised ranch home with ample privacy. Enjoy nature in the many sitting areas in this beautifully landscaped yard with charming bluestone walkway and walls, and lovely shade trees. Upon entering the house the inviting tiled foyer takes you up to the first floor where the first thing you'll notice are those beautiful well cared for

  Rodney Batista Howard Hanna Rand Realty

  12 Arnold Dr, Woodstock, NY 12498
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  /74

  $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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  /37

  $720,000 Open Sat 11AM - 1PM

  • 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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  /62

  $799,000

  • 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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  /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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  /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
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  /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
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  /38

  $795,000

  • 2 Beds
  • 1 Bath
  • 1,250 Sq Ft

  276 Chestnut Hill Rd, Woodstock, NY 12498

  Tucked back on a six acre lot just minutes to the town of Woodstock sits this fairytale two bedroom cottage. The woodland view is yours to explore, the deep forest of evergreens, ferns and moss. Inside, you're tucked into charming spaces or enjoying the expansive Great Room, with a stone fireplace at the center and vaulted ceilings with beautiful exposed beams. A wall of windows frames the view.

  Annabel Taylor Four Seasons Sotheby's Int.

  276 Chestnut Hill Rd, Woodstock, NY 12498
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  /56

  $1,295,000 Open Sat 1PM - 2:30PM

  • 4 Beds
  • 2 Baths
  • 2,377 Sq Ft

  35 Abbey Rd, Mount Tremper, NY 12457

  35 Abbey Road — A Mid-Century Sanctuary minutes from Woodstock TownTucked away off of Abbey Rd and just a short pass over a charming stream you'll arrive at this pristine, authentic mid-century retreat, nestled in the heart of Woodstock's beloved Abbey Road. Set on 5.4 magical acres, this serene property captures the essence of Catskills living- graceful, grounded, and surrounded by

  Quinn Hagstrand BHHS HUDSON VALLEY PROP-WDST

  35 Abbey Rd, Mount Tremper, NY 12457
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  /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
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  /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
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  /33

  $2,175,000

  • 3 Beds
  • 2 Baths
  • 3,100 Sq Ft

  44 Old Wagon Rd, Wood Stock, NY 12498

  Just a short walk from the vibrant village of Woodstock, this exceptional modern contemporary home is truly one-of-a-kind. Designed by a renowned Park Avenue architect, this residence perfectly blends modern design and comfortable living, with no detail overlooked. As you enter through the foyer, you're immediately struck by the abundance of natural light streaming through the wall-to-wall

  Megan Rios Berardi Realty

  44 Old Wagon Rd, Wood Stock, NY 12498
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  /36

  $1,295,000

  • 3 Beds
  • 4 Baths
  • 3,120 Sq Ft

  540 Mount Tobias Rd, Mount Tremper, NY 12457

  Step into the pages of Dwell magazine and immerse yourself in this architect-designed gem offering a harmonious blend of modern design and natural beauty. Feel a wave of calm wash over you, greeted by resplendent views, clean lines, and a wall of windows overlooking majestic mountain vistas. Modernists rejoice. Design aficionados delight. And nature enthusiasts revel. A minimalist aesthetic

  Alexander James Compass Greater NY, LLC

  540 Mount Tobias Rd, Mount Tremper, NY 12457
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  /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

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