Woodstock, NY Homes for Sale with Acreage

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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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  /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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  /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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  /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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  /28

  $1,225,000

  • 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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  /38

  $1,200,000

  • 3 Beds
  • 3.5 Baths
  • 2,337 Sq Ft

  94 the Middle Way, Mount Tremper, NY 12457

  Privately sited on a quiet back road in the Catskills, Noorden House is a modern retreat offering both seclusion and convenience—just 20 minutes to Woodstock, 15 to Phoenicia, and 30 to two ski mountains. Elevated on over 5 acres, the home enjoys distant mountain views, beautifully landscaped grounds, and serene natural features including a heated freeform pool, a small pond, and a picturesque

  Jennifer Grimes Country House Realty Inc

  94 the Middle Way, Mount Tremper, NY 12457
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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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  /38

  $1,182,750

  • 3 Beds
  • 2.5 Baths
  • 2,644 Sq Ft

  241 Silver Hollow Rd, Willow, NY 12495

  A whimsical compound just minutes to the village of Woodstock. On the two acre property you'll find a rushing stream and scenic pond, a three bedroom house, a cabin and a beautiful, modern barn that the current owners use for gatherings, yoga & music. The barn has been entirely rebuilt from the ground up so you'll find new electrical, a new heating & cooling system, local custom millwork, and

  Annabel Taylor Four Seasons Sothebys Intl

  241 Silver Hollow Rd, Willow, NY 12495
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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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  /72

  $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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  /9

  $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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  /11

  $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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  $525,000

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

  296 Maverick Rd, Woodstock, NY 12498

  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, laundry room plus an office, bedroom, workout

  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

  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 throughout, the 1,729 sq ft two-story

  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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  /29

  $799,000

  • 3 Beds
  • 2.5 Baths
  • 2,077 Sq Ft

  1521 Glasco Turnpike, Woodstock, NY 12498

  Tucked away on 2.2 acres of peaceful, park-like grounds, this inviting home offers the perfect blend of privacy, beauty and convenience. A long gravel driveway winds past tall trees and green space, opening to your own hidden haven—set well back from the road, yet just minutes to Woodstock and Saugerties, with their vibrant shops, restaurants, and culture. The approach is unforgettable: a wide

  Kathryn Johnson William Pitt Sotheby's Int'l

  1521 Glasco Turnpike, Woodstock, NY 12498
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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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  /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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  /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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  /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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  /36

  $299,000

  • Land
  • 8 Acres
  • $37,143 per Acre

  00 Lot 2 Church Rd, Woodstock, NY 12409

  Embrace the opportunity to build your dream home in the idyllic surroundings of Woodstock, in beautiful Ulster County. Situated amidst tall evergreens and broadleaf trees with winding bluestone walls you are instantly enveloped in peace and serenity, this parcel offers the perfect setting for your Catskill Mountain retreat.Conscientiously subdivided parcels provide privacy and tranquility

  Melissa McGill Coldwell Banker Village Green

  00 Lot 2 Church Rd, Woodstock, NY 12409
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  /30

  $299,000

  • Land
  • 8 Acres
  • $39,708 per Acre

  0 Lot 1 Church Rd, Woodstock, NY 12409

  Embrace the opportunity to build your dream home in the idyllic surroundings of Woodstock. Situated amidst beautiful evergreen and broadleaf trees with winding bluestone walls you are instantly enveloped in peace and serenity, this parcel offers the perfect setting for your Catskill Mountain retreat.Conscientiously subdivided parcels provide privacy and tranquility with stunning rock

  Melissa McGill Coldwell Banker Village Green

  0 Lot 1 Church Rd, Woodstock, NY 12409
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  /39

  $799,000

  • 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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  /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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