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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  /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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  /63

  $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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  /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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  /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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  /50

  $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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  /34

  $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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  /41

  $990,000

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

  8 Pine Grove St, Woodstock, NY 12498

  Discover the essence of refined country living in this impeccably restored 1920s farmhouse, perfectly positioned in the heart of Woodstock, NY—just 90 miles from New York City. Professionally designed and legally configured as a two-family residence, this unique property offers the rare opportunity for an immediate live/work lifestyle, a multi-generational retreat, or a lucrative rental

  Judy Steinfeld Halter Associates Realty

  8 Pine Grove St, 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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  /47

  $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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  /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
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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

  $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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  /64

  $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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  /49

  $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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  /26

  $499,000

  • 1 Bed
  • 2 Baths
  • 1,729 Sq Ft

  61 W Saugerties Woodstock Rd, Woodstock, NY 12498

  HIGHEST & BEST BY TUESDAY 7/29 AT 10AM!Tucked away at the end of a long, winding drive, this secluded loft-style retreat offers total privacy on six wooded acres in the heart of the Catskills. Surrounded by nature and saturated in light, the home is a sanctuary for artists, musicians, and anyone seeking a slower, more intentional way of life.With a barn-like feel and warm, soulful details

  Laurie Ylvisaker Coldwell Banker Village Green

  61 W Saugerties Woodstock 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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  /44

  $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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  /37

  $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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  /62

  $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

  $829,900

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

  2318 Glasco Turnpike, Woodstock, NY 12498

  Step into the charm of yesteryear while enjoying today's modern comforts. The spacious living room features an oversized stone fireplace with a wood burning insert that warms the entire home on chilly nights. It flows seamlessly into the generous dining area, perfect for hosting large gatherings and opens to a delightful rocking chair porch for relaxing afternoons. The updated galley kitchen

  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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  /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

  Anne Rajs 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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  /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
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  /41

  $495,000

  • 3 Beds
  • 1.5 Baths
  • 1,506 Sq Ft

  3523 Route 212, Bearsville, NY 12409

  WHIMSICAL WOODSTOCK ARTS AND CRAFTS - Live in a home steeped in history while making your own. Welcome to ''Quixote'', built in 1905 by Woodstock builder and former Artificer in the Civil War, John ''Barney'' Hoyt. Vintage character blends seamlessly with modern convenience. Original details of this 3 bedroom, 2.5 bath gem include wide plank floor boards, pressed tin ceilings, custom built-ins

  Peter Cantine Halter Associates Realty

  3523 Route 212, Bearsville, NY 12409
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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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  /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

  • 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
• 

  

  /33

  $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

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