Woodstock, NY Homes for Sale with Acreage

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  $825,000

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

  97 John Joy Rd, Woodstock, NY 12498

  Set beside one of Woodstock's most treasured and enduring landscapes, this quintessential Woodstock property unfolds along the edge of the Thorn Preserve--a protected 60-acre expanse celebrated for its sweeping open grasslands, riparian forest, ponds, and the most artist-captured views of Overlook Mountain. Even more remarkable, this landscape is permanently conserved, ensuring that the

  Richard Vizzini Corcoran Country Living

  97 John Joy Rd, Woodstock, NY 12498
• Explore Woodstock

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  /50

  $1,699,000

  • 8 Beds
  • 5.5 Baths
  • 4,648 Sq Ft

  2320 Glasco Turnpike, Woodstock, NY 12498

  Welcome to The Waterfall House, a truly rare offering nestled in the heart of Woodstock Proper, where nature, creativity, and privacy converge in the most enchanting way. Being offered for the first time, this storied 3,023 sq ft brick colonial is more than a home; it’s an experience, a retreat, and an open canvas for your vision to unfold. Set on nearly 12 acres of lush, mature landscape, the

  Leigh Wagner-Quintana Keller Williams Hudson Valley

  2320 Glasco Turnpike, Woodstock, NY 12498
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  /72

  $1,395,000

  • 3 Beds
  • 3 Baths
  • 2,566 Sq Ft

  1 Wittenberg Rd, Bearsville, NY 12409

  Welcome to Bearsville Record House, a landmark property with a legacy in American music. Built in 1873 and once home to Bearsville Records, this storied compound includes two dwellings; the main farmhouse and a guest cottage, plus a studio building waiting to be finished to your specs. A gunite saltwater pool, outdoor kitchen, and fenced-in plum orchard complete the grounds, all along 500 feet of

  Anthony D'Argenzio Houlihan Lawrence

  1 Wittenberg Rd, Bearsville, NY 12409
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  /52

  $1,275,000

  • 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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  /24

  $1,150,000

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

  540 Mount Tobias Rd, Mount Tremper, NY 12457

  A modernist retreat set against one of the most striking backdrops in the Catskills. 540 Mt. Tobias Road is an architect-designed home where clean lines and expansive glass dissolve the boundary between indoors and out. A wall of windows frames uninterrupted mountain views, pulling light and landscape into every corner of the home. The effect is immediate. Calm, quiet, and completely immersive.

  Alexander James Compass Greater NY, LLC

  540 Mount Tobias Rd, Mount Tremper, NY 12457
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  /30

  $1,167,000

  • 4 Beds
  • 3.5 Baths
  • 2,448 Sq Ft

  9 Munchkin Ln, Kingston, NY 12401

  Selling fully furnished. 9 Munchkin Lane: A Designer Sanctuary in Woodstock Experience turnkey luxury on 5 private, wooded acres. Featured in Instagram’s "Best of Design," this stunning estate is being sold fully furnished—including all high-end decor, electronics, and linens. Just 5 miles from Tinker Street, the home has been meticulously renovated with exposed beams, hardwood floors, and a

  Jonathan Minerick HomeCoin.com

  9 Munchkin Ln, Kingston, NY 12401
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  /42

  $1,199,000

  • 4 Beds
  • 2 Baths
  • 3,378 Sq Ft

  3207-3209 New York 212, Bearsville, NY 12409

  Enchanting Woodstock Compound with a Craftsman Home, Cottage, and Historic Barn. 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 a

  Michelle Bergkamp William Pitt Sotheby's Interna

  3207-3209 New York 212, Bearsville, NY 12409
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  /34

  $1,800,000

  • 4 Beds
  • 5.5 Baths
  • 3,870 Sq Ft

  21 Ori's View Dr, Saugerties, NY 12477

  This dramatic custom home with panoramic Overlook and Berkshire mountain views is located at the end of a long private drive. Enter through lighted stone pillars and past the pond to this light-filled, eco-friendly retreat. There are dramatic mountain views from almost every room. You'll be impressedd by the double height, beamed great room with wide picture windows overlooking the mountains on

  Lisa Halter Halter Associates Realty

  21 Ori's View Dr, Saugerties, NY 12477
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  /15

  $595,000

  • 3 Beds
  • 1.5 Baths
  • 1,133 Sq Ft

  501 Ohayo Mountain Rd, Woodstock, NY 12498

  Discover your Upstate sanctuary in this contemporary 3-bedroom, 1.5-bath gem on Ohayo Mountain Road. Nestled in wooded bliss on 1.8 acres and in close proximity to protected state land, this home delivers a rare sense of peace and enduring natural beauty. Gleaming hardwood floors, a cozy wood-burning stove, and an open-concept floorplan perfect for modern living. Step outside to your private

  James Angelakis BHHS HUDSON VALLEY PROP-WDST

  501 Ohayo Mountain Rd, Woodstock, NY 12498
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  /11

  $499,000

  • Land
  • 15.23 Acres
  • $32,764 per Acre

  Tbd Wardwell Ln, Woodstock, NY 12498

  A rarely available large, 15+ acre parcel in Woodstock -- less than a mile from the center of town! Completely private yet moments away from restaurants, music venues, shops, golf course and hiking. A mixture of mature deciduous and conifer trees offer a forest haven, with level land, rock features and an elevated knoll building site, ready for your next chapter.Much of the heavy lifting has

  Laurie Osmond BHHS HUDSON VALLEY PROP-WDST

  Tbd Wardwell Ln, Woodstock, NY 12498
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  /24

  $549,000

  • 2 Beds
  • 1.5 Baths
  • 1,191 Sq Ft

  208 Tinker St, Woodstock, NY 12498

  TURNKEY WOODSTOCK COTTAGE. A deep violet front door opens to a rustic ''mudroom'' with a bluestone floor and a closet for your outdoor gear. The kitchen, with its Liebherr and Bosch appliances, custom cabinetry with pantry, stylish lighting fixtures, radiant heat, beamed ceiling with a skylight - leads into a light-filled Living/Dining/Den space with original wide-plank wood floors, ceiling fan

  Marilyn Heir BHHS HUDSON VALLEY PROP-WDST

  208 Tinker St, Woodstock, NY 12498
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  /15

  $575,000

  • Land
  • 37 Acres
  • $15,541 per Acre

  00 Lauren Ct, Woodstock, NY 12498

  This spectacular 35+ acre property is a rare offering. Comprised of two separate lots with access points on both Lauren Ct and Church Rd - an open canvas for your boldest vision. Whether you're a developer seeking your next signature project or a homeowner dreaming of a private sanctuary, this land invites imagination and promises possibility. A harmonious blend of mature woodlands, sunlit

  Melissa Zoe Hirsch Coldwell Banker Village Green

  00 Lauren Ct, Woodstock, NY 12498
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  /30

  $749,990

  • 3 Beds
  • 3 Baths
  • 2,718 Sq Ft

  170 MacDaniel Rd, Bearsville, NY 12409

  Driving on this scenic road just minutes from Woodstock, you'll discover a long private driveway leading to a sunlit clearing and attractive raised ranch surrounded by lawns and breathtaking mountain views. After taking in the scenery, step up to the home's welcoming main level, where natural light pours in from all sides. The open living space includes sliders to a large deck perfect for

  Judy Steinfeld Halter Associates Realty

  170 MacDaniel Rd, Bearsville, NY 12409
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  /48

  $729,000

  • 1 Bed
  • 2 Baths
  • 1,128 Sq Ft

  14 Lions Way, Shady, NY 12409

  The essence of Woodstock; the artists, the poets, the musicians and the creatives who have gravitated to the beautiful, iconic Catskill Mountain town, no-one embodies the original spirit of Woodstock more than local artist and environmentalist Calvin Grimm. Every home tells a story. This hand built 1 Bd/ 2 Ba with additional flex room and art studio tucked away on 2 private acres on a dead end

  Johanna Trimboli Halter Associates Realty

  14 Lions Way, Shady, NY 12409
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  /13

  $135,000

  • Land
  • 2 Acres
  • $67,500 per Acre

  0 Lot Cross Patch Rd, Woodstock, NY 12495

  Come experience the restorative powers of a mediative rest along side a rushing mountain creek. This 2 acre parcel with frontage on the East Branch of the Silver Hollow Creek will be an amazing location to build that country home that you have been envisioning. There is survey and preliminary site plan sketch to help you envision your dream. This parcel features a 19th Century building foundation

  Sean Zimmerman Halter Associates Realty

  0 Lot Cross Patch Rd, Woodstock, NY 12495
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  /30

  $849,000

  • 4 Beds
  • 2.5 Baths
  • 2,584 Sq Ft

  1 Stone Ridge Ct, Woodstock, NY 12498

  Tucked into a quiet cul-de-sac, this spacious 4-bedroom, 2.5-bath Colonial features a gorgeous in-ground swimming pool surrounded by mature plantings. With a comfortable, easy flow, a welcoming foyer opens to a bright main level that connects the living room, dining area, and updated kitchen.The kitchen is equipped with granite countertops and stainless-steel appliances, while the bathrooms

  Susanna Scott-Mitchell Compass Greater NY, LLC

  1 Stone Ridge Ct, Woodstock, NY 12498
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  $4,900,000 Open Sun 11AM - 1PM

  • 3 Beds
  • 6 Baths
  • 4,688 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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  /18

  $799,000

  • Land
  • 27.19 Acres
  • $29,386 per Acre

  TBD MacDaniel Rd, Bearsville, NY 12409

  Pollinator's Pathway in Woodstock Discover 27+ acres of untouched beauty just steps from the Tibetan Monastery, Magic Meadow, and the trailheads to Meads Mountain and Overlook Mountain. A private, winding ~.5-mile driveway opens to a sunlit clearing alive with wildflowers and pollinator plants — a natural canvas awaiting your vision. With selective tree trimming, sweeping Catskill Mountain views

  Genevieve Geaney Compass Greater New York, LLC

  TBD MacDaniel Rd, Bearsville, NY 12409
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  /7

  $495,000

  • Land
  • 15 Acres
  • $33,000 per Acre

  256 MacDaniel Rd, Bearsville, NY 12409

  Rare opportunity to create your dream home on a magical piece of property! Private/ quiet road, yet minutes from the center of the town of Woodstock, with all it has to offer! Potential majestic mountain views, with clearing. A dirt road leading up to the property is already in place. This 15 acre parcel of land is located on one of the Woodstock area's most coveted roads. The Karma Triyana

  Corinne Gervai Coldwell Banker Village Green

  256 MacDaniel Rd, Bearsville, NY 12409
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  /10

  $158,000

  • Land
  • 2.1 Acres
  • $75,238 per Acre

  00 Whites Ln, Woodstock, NY 12498

  PRICE REDUCEDPrime location offering both privacy and proximity to the heart of Woodstock Village. Although the parcel's address is Whites Lane it is a fully wooded lot fronting Playhouse Lane Extension, a private and secluded road starting at the junction of Whites Lane and Playhouse. This setting is ideal for building your dream home while enjoying the convenience of walking to the Village.

  Daniel Hauspurg Potter Realty

  00 Whites Ln, Woodstock, NY 12498
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  $585,000

  • 2 Beds
  • 2 Baths
  • 1,365 Sq Ft

  171 W Hurley Rd, Woodstock, NY 12498

  Stylish, single-story living: This fully reinvented bungalow is convenient to both Woodstock and Kingston, and features large over-sized rooms and systems, all in a tight semi-open layout that takes full advantage of its over-sized 2+ acre wooded parcel. Grounded by hardwood or polished-concrete floors throughout and topped by dramatic cathedral ceilings in most rooms, the house features two main

  Hayes Clement Compass Greater New York, LLC

  171 W Hurley Rd, Woodstock, NY 12498
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  /33

  $569,000

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  328 John Joy Rd, Woodstock, NY 12498

  Nearly Six Lush, Scenic And Private Acres Located Eight Minutes From The Heart Of Woodstock! This Home Features Two / Possibly Three Bedrooms And Two Full Baths. Meticulously Maintained! Enjoy Sunrises Or Sunsets From The Wrap Around Deck. Relax And Take In All Of The Tranquility While Sitting Stream Side Or Enjoy The Changing Of The Leaves During The Beautiful Fall Season While Sipping Hot Cocoa

  Michael Alpert Daniel Gale Sothebys Intl Rlty

  328 John Joy Rd, Woodstock, NY 12498
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  /42

  $895,000

  • 3 Beds
  • 3 Baths
  • 2,316 Sq Ft

  5 Maverick Terrace, Woodstock, NY 12498

  Tucked away on a peaceful, wooded lane, this inviting home offers the perfect blend of privacy, space, and convenience- just minutes to the heart of Woodstock. Inside, the home opens to an expansive living room anchored by a beautiful brick fireplace, creating a warm and inviting centerpiece for gatherings or quiet evenings. This oversized space includes a full bathroom and flows effortlessly to

  Dominique Musialkiewicz Howard Hanna Rand Realty

  5 Maverick Terrace, Woodstock, NY 12498
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  /28

  $2,250,000

  • 4 Beds
  • 3 Baths
  • 3,539 Sq Ft

  9 Black Bear Rd, Bearsville, NY 12409

  Tucked just beyond the heart of Woodstock, down a private road off a quiet dead-end street, this completely renovated home feels like a secret you're lucky to have discovered. Just 2.5 miles from town and moments from the Bearsville Theatre, the setting is both deeply private and wonderfully connected.While the exterior presents a discreet, understated presence, the interior unfolds into a

  Alexis Li Corcoran Country Living

  9 Black Bear Rd, Bearsville, NY 12409
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  /34

  $1,475,000

  • Land
  • 25.38 Acres
  • $58,117 per Acre

  132 Valley View Way, Woodstock, NY 12448

  The Ledges at Valley View High above the Beaverkill River, where the Catskills unfold in a sweep of peaks and light, lies The Ledges at Valley View - a design-ready estate site where modern architecture meets the mountain. Sited on more than 25 private acres, this south-facing ridgeline property captures cinematic views of Twin, Indian Head, Overlook, and Mount Guardian. The land adjoins more

  Margaret Bellar The Catskill Dream Team

  132 Valley View Way, Woodstock, NY 12448
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  /28

  $1,750,000

  • Land
  • 60.94 Acres
  • $28,717 per Acre

  Tbd Mulberry Ln, Woodstock, NY 12498

  An incredible, rare opportunity in Woodstock. It has been very long time since a parcel of this magnitude has available for sale in Woodstock. This contiguous 60-acre property, consisting of two 30-acre lots, features rolling hills, stunning rock outcroppings, mountain views, and diverse mature trees, uniquely offering both beauty and potential. A privately built road, completed by the owners,

  Baris Demirel Serhant LLC

  Tbd Mulberry Ln, Woodstock, NY 12498
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  /61

  $760,000

  • 2 Beds
  • 1.5 Baths
  • 1,410 Sq Ft

  15 Lake View Dr, Lake Hill, NY 12448

  Own this stunning, architect-designed contemporary home in Woodstock, NY. Professionally decorated and thoughtfully crafted with passive solar principles, this energy-efficient residence seamlessly blends modern design with its natural surroundings. Set just across the road from the famous Cooper Lake, the home is nestled in a beautiful, 3 acre wooded setting—private yet not isolated—surrounded

  Mackenzie Grate The Machree Group, LLC

  15 Lake View Dr, Lake Hill, NY 12448
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  /70

  $3,600,000 Open Sun 11AM - 1PM

  • 4 Beds
  • 4 Baths
  • 5,272 Sq Ft

  306 Meads Mountain Rd, Woodstock, NY 12498

  Inside Swoop House there is a versatile floor plan that includes four en suite bedrooms, one an attached guest suite, and two two-story great rooms, one of which was designed as a professional art studio. Designed by FT Architecture & Interiors and inspired by the Diller Scofidio Slow House, two non-parallel curved walls and sloping ceilings create a graceful series of shapes. This singular

  Kimberly Cantine Halter Associates Realty

  306 Meads Mountain Rd, Woodstock, NY 12498
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  /31

  $2,400,000

  • 5 Beds
  • 4.5 Baths
  • 2,978 Sq Ft

  177 Tinker St, Woodstock, NY 12498

  Fall in love with this artfully reimagined and expanded 1930 farmhouse, privately set on a gentle hill just moments from the heart of Woodstock. Rich in history and character, this special home was once owned by Michael Lang, the legendary founder of the 1969 Woodstock Festival—adding a rare and meaningful connection to the town's iconic past.Thoughtfully renovated, the home offers a

  Joan Capria Four Seasons Sotheby's Int'l R

  177 Tinker St, Woodstock, NY 12498
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  /29

  $1,499,900

  • 3 Beds
  • 4 Baths
  • 3,330 Sq Ft

  106 Mountain Laurel Ln, Woodstock, NY 12498

  A truly one-of-a-kind residence and rare opportunity, this exceptional home offers a seamless blend of architecture and art in the heart of Woodstock, walking distance to Tinker Street, yet set privately on 1.73 secluded acres just minutes from the village.Designed as a fusion of a Frank Lloyd Wright–inspired contemporary addition and an original Buckminster Fuller–style geodesic dome, the

  Ashley Olson Minard eXp Realty

  106 Mountain Laurel Ln, Woodstock, NY 12498
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  /6

  $184,900

  • Land
  • 2.31 Acres
  • $80,043 per Acre

  100 Zena Rd, Woodstock, NY 12498

  One of the last commercial lots in Woodstock. Zoned neighborhood commercial..excellent drainage. Great location for nursery school, medical or dental clinic, funeral home, or professional office, bank retail mix strip complex. Based on Zoning and bulk requirements site can facilitate approx. 16,000 sq. ft. of building...Soil has excellent drainage for inground septic system. The Town Building

  Michael Bernholz Sr. Hudson Valley Appraisal

  100 Zena Rd, Woodstock, NY 12498
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  /46

  $1,295,000

  • 3 Beds
  • 2 Baths
  • 1,817 Sq Ft

  36 Summers Ln, Woodstock, NY 12498

  Tucked into Woodstock's coveted Upper Byrdcliffe arts enclave, this thoughtfully built contemporary offers a rare combination of privacy, architectural character and effortless access to the village. Set on two acres with seasonal mountain views, the property blends modern comfort with artistic heritage in one of Woodstock's most sought after locations. The main house features 3 bedrooms and 2

  Valerie Cashen Coldwell Banker Village Green

  36 Summers Ln, Woodstock, NY 12498
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  /19

  $590,000

  • 2 Beds
  • 2 Baths
  • 2,040 Sq Ft

  4 Ashley Ln, Woodstock, NY 12498

  Totally private two bedroom and two bath contemporary home bordering 44 acres of DEP protected land. Just off Mink Hollow Road in the hamlet of Lake Hill. Drive down long driveway to discover an artesian spring pond, garden beds, perennials and forest. Main living area on first floor includes open kitchen, dining and living room. Breakfast bar, wood cabinets and custom tile backsplash with window

  Jennifer Mangione Grist Mill Real Estate

  4 Ashley Ln, Woodstock, NY 12498
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  /41

  $895,000

  • 3 Beds
  • 2.5 Baths
  • 2,264 Sq Ft

  168 Cooper Lake Rd, Bearsville, NY 12409

  Set on one of Woodstock's most coveted country roads, this classic home offers the rare combination of timeless charm, privacy, and an exceptional location. Just moments from the heart of Woodstock, yet quietly removed, Cooper Lake Road is known for its scenic beauty, peaceful surroundings, and idyllic walks to nearby Cooper Lake. Originally built in 1940 and renovated over the years, this

  Melissa Mayes Serhant LLC

  168 Cooper Lake Rd, Bearsville, NY 12409
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  /17

  $1,995,000

  • 8 Beds
  • 10 Baths
  • 12,393 Sq Ft

  20 Country Club Ln, Wood Stock, NY 12498

  Experience the legacy of Woodstock through this extraordinary historic offering. Once home to the iconic Woodstock Lodge and The Pinecrest, this storied 6.5-acre property offers a unique opportunity to reimagine a legacy estate in one of the Hudson Valley's most sought-after destinations. Set on scenic, gently rolling land with a blend of open clearings, wooded trails, and a seasonal stream, the

  Kathryn Johnson William Pitt Sotheby's Interna

  20 Country Club Ln, Wood Stock, NY 12498
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  /49

  $3,500,000

  • 4 Beds
  • 4 Baths
  • 4,201 Sq Ft

  289 Upper Byrdcliffe Rd, Woodstock, NY 12498

  Set on nearly 9 serene acres in the heart of Woodstock's historic Byrdcliffe Arts Colony is a rare synthesis of architectural precision and natural harmony—an embodiment of award-winning architect John Storyk's deep understanding of space, sound, and site. Designed in 1969 at the very beginning of Storyk's now-legendary career—just after his groundbreaking work on Jimi Hendrix's Electric Lady

  Sharon Breslau BHHS HUDSON VALLEY PROP-WDST

  289 Upper Byrdcliffe Rd, Woodstock, NY 12498
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  /23

  $600,000

  • Land
  • 5.45 Acres
  • $110,092 per Acre

  326 Raycliffe Dr, Woodstock, NY 12498

  Discover a rare opportunity to own 5.45 acres atop one of Woodstock's most coveted locations. This private, east-facing lot offers panoramic views that stretch endlessly over the Catskill Mountains, providing an awe-inspiring backdrop for your dream home. With the space and natural beauty to build a sleek, modern estate, this land is the perfect canvas for a luxury retreat. Surrounded by the

  Alexis Li Corcoran Country Living

  326 Raycliffe Dr, Woodstock, NY 12498
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  /36

  $596,000

  • 3 Beds
  • 1 Bath
  • 1,187 Sq Ft

  28 Shultis Farm Rd, Bearsville, NY 12409

  Longing for the vibrant artistic Woodstock community but yearning for serene and peaceful country living? This is it! This charming and quaint one level cottage in a bucolic setting with mountain views is sure to check all the boxes. The expansive landscaped lawn offers a multitude of flower bushes and fruit trees. A pond sits at the edge of the property while the babbling brook in the back is

  Sylvie Ross Halter Associates Realty

  28 Shultis Farm Rd, Bearsville, NY 12409
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  /33

  $799,000

  • 4 Beds
  • 2.5 Baths
  • 2,340 Sq Ft

  12 Oriole Dr, Woodstock, NY 12498

  A bright and sunny Colonial gem just minutes into the center of Woodstock! This home is set far back and hidden from the road creating a true sense of privacy. Coming down the driveway, you begin to see the 1.47 acre yard wrapping around the house which is partially bordered by a charming stone wall. Once inside, the spacious living room is on your left with built-in bookcases and a fireplace

  Richard Stoll Halter Associates Realty

  12 Oriole Dr, Woodstock, NY 12498
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  /26

  $349,000

  • Land
  • 3 Acres
  • $116,333 per Acre

  547 Glenford Wittenberg Rd, Bearsville, NY 12409

  Three acres available on Yankee Town Pond in Bearsville. Convenient to Woodstock yet only 15 minutes to the NYS Thruway. Minutes to the Ulster County Rail Trail w hiking and biking all at your fingertips. Love to fish? This is perfect. This lot is being subdivided from a larger parcel and will be a buildable lot with engineered plans for the house. The taxes and assessment reflect the entire

  Siobhan Scanlan Win Morrison Realty-K

  547 Glenford Wittenberg Rd, Bearsville, NY 12409

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