Woodstock, NY Homes for Sale with Acreage

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  /46

  $695,000

  • 3 Beds
  • 2 Baths
  • 1,842 Sq Ft

  47 van de Bogart Rd, Woodstock, NY 12498

  Set well back from the road and sited on 4+ acres, this wonderful 1935 farmhouse has been updated over the years yet retains its original charm and character. Most recent upgrades within the year include a new kitchen with marble and butcherblock counters, a completely renovated main bathroom, new roof, and more. The grounds are lovely with established perennials, level grassy meadow and woods to

  

  Amy Lonas

  Coldwell Banker Village Green

  47 van de Bogart Rd, Woodstock, NY 12498
• Explore Woodstock

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  /74

  $1,195,000

  • 5 Beds
  • 4 Baths
  • 3,475 Sq Ft

  388-390 Wittenberg Rd, Bearsville, NY 12409

  A rare opportunity just minutes from the heart of historic Woodstock, this exceptional country compound pairs the timeless character of a beautifully updated farmhouse with the privacy and tranquility of an estate-like setting. A long private drive unfolds through peaceful, park-like grounds where meadow, mature woods, gardens, and abundant nature create a remarkable sense of seclusion so close

  Eric Amaral Coldwell Banker Village Green

  388-390 Wittenberg Rd, Bearsville, NY 12409
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  /56

  $2,300,000

  • 3 Beds
  • 4 Baths
  • 2,613 Sq Ft

  56 Lauren Ct, Woodstock, NY 12498

  Exceptional 3 bedroom, 4 bath light-filled contemporary home offering refined nouvelle living set on over 4 private acres in Woodstock, NY. This home has had a complete interior high-end designer renovation that has been thoughtfully curated with sophisticated finishes and fine craftsmanship blending seamless luxury, comfort, and architectural elegance.A dramatic great room framed by soaring

  Amy Owens Coldwell Banker Village Green

  56 Lauren Ct, Woodstock, NY 12498
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  /37

  $699,000

  $50K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,991 Sq Ft

  72 Van Dale Rd, Woodstock, NY 12498

  Nestled in a quiet Woodstock neighborhood five minutes from the village center and a short drive from Kingston, The Van Dale offers the privacy of nature without sacrificing convenience. Set on 1.36 acres in a quiet neighborhood, the property is bordered by a private creek that winds through the backyard, creating a peaceful natural setting just minutes from some of the Hudson Valley's most

  Leslie Foti Coldwell Banker Village Green

  72 Van Dale Rd, Woodstock, NY 12498
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  /40

  $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
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  /44

  $2,995,000

  $330K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,975 Sq Ft

  35 Van Wagner Rd, Willow, NY 12495

  More than a century in the making, and unlike anything else on the market, this extraordinary multi-residential estate began as a historic Hudson Valley farm before being thoughtfully transformed into a modern lifestyle retreat of remarkable scale and character. Over the years, musicians, entrepreneurs, and creative thinkers have called it home. Prior to that, it served as the Woodstock Farm

  Laurie Ylvisaker Coldwell Banker Village Green

  35 Van Wagner Rd, Willow, NY 12495
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  /42

  $2,300,000

  • 3 Beds
  • 4 Baths
  • 3,481 Sq Ft

  56 Lauren Ct, Kingston, NY 12401

  Exceptional 3 bedroom, 4 bath light-filled contemporary home offering refined nouvelle living set on over 4 private acres in Woodstock, NY. This home has had a complete interior high-end designer renovation that has been thoughtfully curated with sophisticated finishes and fine craftsmanship blending seamless luxury, comfort, and architectural elegance. A dramatic great room framed by soaring

  Amy Owens Coldwell Banker Village Green

  56 Lauren Ct, Kingston, NY 12401
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  /49

  $799,999

  $25K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,372 Sq Ft

  29 Maurizi Ln, Woodstock, NY 12498

  Set on an almost 3-acre wooded lot, this property has so much to offer in a quiet location close to the Village Green. On the main floor, you have a choice of rooms in which to entertain. A generous foyer leads to a comfortable living room with an actual dining room opposite. Beyond that space, a bright, recently redone, cheery eat-in kitchen awaits. Down the hall, for those cozy nights, a

  Henry Ford Coldwell Banker Village Green

  29 Maurizi Ln, Woodstock, NY 12498
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  /14

  $199,000

  • Land
  • 3.19 Acres
  • $62,382 per Acre

  Lot 6 Mount Guardian Rd, Bearsville, NY 12409

  Discover 3.19 wooded acres in the heart of Bearsville, offering a rare opportunity to create your own Hudson Valley retreat just minutes from Woodstock. Set at the corner of Mt. Guardian Road and Mt. Guardian Road Extension, this fully wooded residentially zoned parcel is located along a privately maintained road in a peaceful, natural setting. Surrounded by the beauty and character that make the

  STEVEN WROBEL JR. Serhant LLC

  Lot 6 Mount Guardian Rd, Bearsville, NY 12409
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  /30

  $1,150,000

  • 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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  /8

  $249,000

  • Land
  • 10 Acres
  • $24,900 per Acre

  4912 Ny-212, Willow, NY 12495

  Discover the opportunity to create your dream escape on this serene 10-acre parcel nestled in the quiet hamlet of Willow, NY. Tucked away in nature yet just a short drive from the vibrant village of Woodstock, this expansive property offers the perfect blend of privacy and proximity. Towering trees, dappled sunlight, and the calming sounds of nature create a peaceful setting for your future home,

  Richard Vizzini Corcoran Country Living

  4912 Ny-212, Willow, NY 12495
• 

  

  /14

  $199,000

  • Land
  • 3.19 Acres
  • $62,382 per Acre

  Lot 6 Mt Guardian Rd, Bearsville, NY 12498

  Discover 3.19 wooded acres in the heart of Bearsville, offering a rare opportunity to create your own Hudson Valley retreat just minutes from Woodstock. Set at the corner of Mt. Guardian Road and Mt. Guardian Road Extension, this fully wooded residentially zoned parcel is located along a privately maintained road in a peaceful, natural setting.Surrounded by the beauty and character that make

  STEVEN WROBEL JR. Serhant LLC

  Lot 6 Mt Guardian Rd, Bearsville, NY 12498
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  /39

  $1,295,000

  $200K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,731 Sq Ft

  41 Wittenberg Rd, Woodstock, NY 12498

  Hidden among the trees and just seven minutes from the center of Woodstock, this 1970s contemporary feels like a private creative compound, untouched in all the right ways.Set on 2 wooded acres with the Sawkill Creek at the rear of the property, the home unfolds through a series of unexpected spaces and strong architectural moments. A dramatic sunken living room anchors the house,

  Kathryn Johnson William Pitt Sothebys Int Rlty

  41 Wittenberg Rd, Woodstock, NY 12498
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  /13

  $599,000

  • Land
  • 7.18 Acres
  • $83,426 per Acre

  Lot 2 11 Marion's Way, Woodstock, NY 12498

  A once-in-a-generation opportunity to create your dream home in the heart of Woodstock, the coolest small town in America. Nestled on 7 shovel-ready acres just moments from the vibrant village center, this exceptional property offers the perfect balance of privacy, natural beauty, and convenience. Steeped in local history, the land is one of the last remaining vacant parcels from an historic

  Joel Craig Coldwell Banker Village Green

  Lot 2 11 Marion's Way, Woodstock, NY 12498
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  /61

  $3,950,000

  • 7 Beds
  • 4 Baths
  • 3,948 Sq Ft

  21-23 Library Ln, Woodstock, NY 12498

  There are places that transcend the idea of home, offering a way of life shaped by beauty, history, and nature. Library Lane Estate, a historically significant property in the heart of Woodstock, is where architectural heritage, artistic provenance, and landscape converge. Nestled along a quiet lane just moments from the village, it offers a rare balance of privacy, connection, and a profound

  Sarah Broach Compass Greater NY, LLC

  21-23 Library Ln, Woodstock, NY 12498
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  /82

  $2,600,000

  • 2 Beds
  • 2 Baths
  • 1,511 Sq Ft

  2673 Glasco Turnpike, Woodstock, NY 12498

  History abounds at this remarkable estate, reached by a quarter-mile-long drive offering complete seclusion across 43+ acres spanning two parcels. Sited below the slopes of the historic Byrdcliffe Arts Colony and adjacent to the legendary Grossman estate, the property offers a rare combination of privacy, natural beauty, and Woodstock history.The property features three main buildings: a

  Henry Ford Coldwell Banker Village Green

  2673 Glasco Turnpike, Woodstock, NY 12498
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  /26

  $399,000

  • 1,000 Sq Ft

  281 Cold Brook Rd, Bearsville, NY 12409

  There are homes that ask you to compromise, and then there are homes that ask you to dream.Set against a backdrop of sweeping mountain views, this is a rare opportunity to create something that’s unmistakably yours. The hardest work has already been done. What’s left is the part that reflects your style, your vision, and the way you want to live.Picture slow mornings with coffee

  Ron Knowles Century 21 Alliance Rlty Group

  281 Cold Brook Rd, Bearsville, NY 12409
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  /33

  $595,000

  • 2 Beds
  • 2 Baths
  • 1,321 Sq Ft

  419 Sickler Rd, Willow, NY 12495

  Relax, unwind, and take in the views from this charming cottage on one of the most bucolic and peaceful roads in the Woodstock hamlet of Willow--where every day feels like a weekend escape.The tranquility, mountain views, and picturesque valley setting have been cherished by one family for 47 years.Tucked away from the road and nearly invisible to passersby, the property welcomes

  Marcia Weiss Halter Associates Realty

  419 Sickler Rd, Willow, NY 12495
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  /34

  $569,000

  • 2 Beds
  • 1 Bath
  • 980 Sq Ft

  495 Silver Hollow Rd, Willow, NY 12495

  Situated at the very end of Silver Hollow set against the Catskill Forest with hundreds of acres of forever wild DEP land, sits this privately sited, newly renovated 2 Bd/ 1 Ba quintessential Catskill Mountain home with Warner Creek frontage. Designed in 1971 by a commercial artist from London who had a robust career in NYC, he executed his design in 1972 with the vision of creating a country

  Johanna Trimboli Halter Associates Realty

  495 Silver Hollow Rd, Willow, NY 12495
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  /36

  $1,700,000

  • 5 Beds
  • 5 Baths
  • 4,628 Sq Ft

  7 Downer Ln, Woodstock, NY 12498

  A Woodstock compound with two distinct residences on eight acres, currently set up as STR. Included as part of this unique offering, 7 Downer Road brings an entirely different yet equally compelling dimension to the property. Set on approximately two private acres with beautiful mountain views, this authentic mid-century ranch captures the simplicity and warmth.The one-bedroom home

  Baris Demirel Serhant LLC

  7 Downer Ln, Woodstock, NY 12498
• 

  

  /13

  $599,000

  • Land
  • 7.18 Acres
  • $83,426 per Acre

  Lot 2 11 Marions Way, Woodstock, NY 12498

  A once-in-a-generation opportunity to create your dream home in the heart of Woodstock, the coolest small town in America. Nestled on 7 shovel-ready acres just moments from the vibrant village center, this exceptional property offers the perfect balance of privacy, natural beauty, and convenience. Steeped in local history, the land is one of the last remaining vacant parcels from an historic

  Joel Craig Coldwell Banker Village Green

  Lot 2 11 Marions Way, Woodstock, NY 12498
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  /63

  $895,000

  $20K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,265 Sq Ft

  15 Chipmunk Ln, Woodstock, NY 12498

  Rarely does a Woodstock home come along with this much soul, flexibility, and built-in opportunity. Tucked away on just over an acre off private Chipmunk Lane, this charming 2265 sq ft Cape Cod cottage style home captures the feeling people come to Woodstock hoping to find: a little privacy, a little magic, a little room to create, and a home that feels deeply personal from the moment you

  Dylan Taft Taft Street Realty, Inc.

  15 Chipmunk Ln, Woodstock, NY 12498
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  /50

  $1,195,000

  $130K PRICE DROP

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

  2320 Glasco Turnpike, Woodstock, NY 12498

  Welcome to The Waterfall House, a rare opportunity tucked away in the heart of Woodstock Proper. Set on nearly 12 private acres, this classic brick Colonial offers an exceptional combination of privacy, natural beauty, and endless potential, all just minutes from the shops, restaurants, galleries, and vibrant arts scene that have made Woodstock an iconic destination.Offering approximately

  Leigh Wagner-Quintana KW Hudson Valley North

  2320 Glasco Turnpike, Woodstock, NY 12498
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  /34

  $799,000

  $50K PRICE DROP

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

  1 Stone Ridge Ct, Woodstock, NY 12498

  Private Woodstock retreat with a heated in-ground pool, set on 1.21 beautifully landscaped acres located on a quiet cul-de-sac. This spacious 4-bedroom, 2.5-bath home offers 2,584 square feet of versatile living space.The heart of the property is the outdoor space, with a heated 18' x 36' in-ground pool, bluestone patio and mature landscaping creating your own private summer retreat. A

  Susanna Scott-Mitchell Compass Greater NY, LLC

  1 Stone Ridge Ct, Woodstock, NY 12498
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  /49

  $3,600,000

  • 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 Inc

  306 Meads Mountain Rd, Woodstock, NY 12498
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  /32

  $3,650,000

  New Construction $350K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,750 Sq Ft

  2 Stonecreek Rd, Woodstock, NY 12498

  Stonecreek is a one-of-a-kind newly constructed turnkey furnished designerresidence conceived and designed with Dichotomy Interiors, brought to lifethrough a female-led collaboration rooted in design, craftsmanship, and adeep connection to the surrounding landscape, set on 8.3 private acres within101 acres of protected conservation land just five minutes from Tinker Street

  Sheena Lepez Compass Greater New York, LLC

  2 Stonecreek Rd, Woodstock, NY 12498
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  /14

  $2,175,000

  • 9 Beds
  • 5 Baths
  • 4,000 Sq Ft

  589-595 Plank Rd, Mount Tremper, NY 12457

  Legendary Estate & Compound on the Esopus Creek. **A Historic Masterpiece with a Superhero Pedigree** Steeped in history and once owned by **George Reeves**, the iconic star of the 1950s *Superman*, this meticulously renovated 1870s farmhouse compound offers a lifestyle of unparalleled versatility. Spanning **5+ park-like acres** with direct **Esopus Creek water frontage**, this sprawling estate

  Derek Greene Greene Realty Group

  589-595 Plank Rd, Mount Tremper, NY 12457
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  /91

  $795,000

  Open Sat 12AM - 3PM

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

  4868 State Route 212, Willow, NY 12495

  Income Opportunity! This residential property includes a transferable short-term rental license, excellent investment and income-producing potential.Beautifully renovated and thoughtfully updated with numerous high-end upgrades, see below, this versatile 4-5 bedroom, 3-full bath home sits on 3.6 private acres with breathtaking views of Ohayo Mountain, Mount Guardian, Mount Tremper, and

  Ruti kabel Keller Williams Realty HV Nort

  4868 State Route 212, Willow, NY 12495
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  /68

  $865,000

  $113K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,410 Sq Ft

  25-29 Mink Hollow Rd, Woodstock, NY

  Directly across from Cooper Lake and tucked quietly among the trees just minutes from Woodstock, this rare Catskills compound captures the kind of escape buyers dream about but rarely find. Surrounded by woods, mountain air, hiking, legendary fly-fishing waters, and the natural beauty that defines the Catskills, the property offers a unique blend of privacy, flexibility, creative space, and

  Yan Wang Realty One Group Key

  25-29 Mink Hollow Rd, Woodstock, NY
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  /50

  $1,395,000

  • 3 Beds
  • 3 Baths
  • 2,258 Sq Ft

  7 Wilber Ln, Woodstock, NY 12498

  ROOMS WITH A VIEW! Welcome to 7 Wilber Lane, a stylish mid-century modern ranch set on four glorious acres in the heart of Woodstock, where nearly every room connects you to the beauty outside. Overlook Mountain provides a magnificent backdrop to established gardens, open sky and a wonderfully wild landscape where more than 40 species of birds have been observed.Inside, the home unfolds

  Jeanne Rakowski Corcoran Country Living

  7 Wilber Ln, Woodstock, NY 12498
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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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  /51

  $2,400,000

  • 2 Beds
  • 2 Baths
  • 1,904 Sq Ft

  262 MacDaniel Rd, Bearsville, NY 12409

  Wend up your forested driveway to this idyllic piece of paradise -- 12 secluded acres, just minutes from Woodstock Village. The current owner/architect/builder designed this uniquely curated home and its surroundings to create the penultimate natural setting. As the house is revealed through the trees, a mirror image is reflected in the 13' deep, swimmable, mini-lake. BREATHE! That's the perfect

  Sharon Breslau BHHS HUDSON VALLEY PROP-WDST

  262 MacDaniel 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

  Kathryn Johnson William Pitt Sothebys Int Rlty

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

  $600,000

  • Land
  • 28.17 Acres
  • $21,299 per Acre

  465 Sickler Rd, Willow, NY 12495

  28+ Acres in Woodstock with Views Set at the foot of Mt. Tobias and surrounded by protected state and conservancy land on all sides, this exceptional 28+ acre parcel offers a rare opportunity to build with lasting privacy just minutes from the heart of Woodstock. An established driveway leads to a thoughtfully cleared build site where expansive valley and mountain views create a stunning backdrop

  Leigh Bokser Compass Greater NY, LLC

  465 Sickler Rd, Willow, NY 12495
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  /51

  $675,000

  $55K PRICE DROP

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

  15 Lake View Dr, Lake Hill, NY 12448

  15 Lake View Drive | Lake Hill, NYA modern Catskills retreat with thoughtful architecture, natural beauty, and Cooper Lake just across the road.Set on three wooded acres in Lake Hill, this distinctive architect-designed contemporary offers a rare combination of privacy, design, and proximity to the best of the Hudson Valley. Tucked among mature trees and dramatic natural

  Mackenzie Grate The Machree Group, LLC

  15 Lake View Dr, Lake Hill, NY 12448
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  /61

  $889,000

  • 4 Beds
  • 3 Baths
  • 2,410 Sq Ft

  25-29 Mink Hollow Rd, Lake Hill, NY 12448

  Yan Wang REALTY ONE GROUP KEY

  25-29 Mink Hollow Rd, Lake Hill, NY 12448
• 

  

  /44

  $1,325,000

  $250K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,360 Sq Ft

  94 Chestnut Hill Rd, Woodstock, NY 12498

  A rare opportunity to own a truly special piece of the Hudson Valley. Nestled in the heart of Woodstock, NY, this iconic property offers 11.17 breathtaking acres of open meadows and sweeping mountain views that change beautifully with every season.The well-maintained 3-bedroom, 1-bath ranch house spans 1,360 square feet and offers comfortable single-level living with a warm, classic

  Henry Ford Coldwell Banker Village Green

  94 Chestnut Hill Rd, Woodstock, NY 12498
• 

  

  /40

  $865,000

  Open Sat 12PM - 2PM

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

  168 Cooper Lake Rd, Woodstock, NY 12498

  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 portion of the house possibly dates to 1875 with

  Melissa Mayes Serhant LLC

  168 Cooper Lake Rd, Woodstock, NY 12498
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  /33

  $569,000

  $30K PRICE DROP

  • 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
• 

  

  /33

  $300,000

  $195K PRICE DROP

  • Land
  • 5.4 Acres
  • $55,556 per Acre

  334 Yerry Hill Rd, Woodstock, NY 12498

  Tucked away just minutes from the heart of Woodstock, this exceptional 5-acre parcel offers a rare opportunity to create something truly special in one of the Hudson Valley's most sought-after locations. Surrounded by mature woods and natural beauty, the property features the serene Little Beaver Kill winding through the land along with seasonal mountain views from the upper elevation, creating

  Eliana Amodio Amodio Real Estate & Prop

  334 Yerry Hill Rd, Woodstock, NY 12498

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