Homes for Sale near Woodstock Day School

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  /31

  $975,000

  • 4 Beds
  • 4 Baths
  • 1,811 Sq Ft

  33 Tannery Brook Rd, Woodstock, NY 12498

  Nestled in the heart of Woodstock, this beautifully transformed farmhouse, originally constructed in the 1870s, seamlessly blends historic charm with modern living. The current owners, a talented architect and interior designer, have meticulously renovated this property to enhance its original architecture while maximizing natural light and integrating the surrounding landscape. The zoning allows

  

  Danielle Sevier

  Compass Greater NY, LLC

  (845) 456-8466

  33 Tannery Brook Rd, Woodstock, NY 12498
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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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  /32

  $1,195,000

  • 4 Beds
  • 6 Baths
  • 2,980 Sq Ft

  12 Tinker St, Woodstock, NY 12498

  Prime Village Green Historic Gem in Woodstock, NY. Discover a unique opportunity to own a piece of history in the heart of Woodstock. This remarkable 1875 era property originally known as The Snyder Homestead named after its original owner, was the grandest house in town. This old style home with its distinctive Mansard roof retains its grandeur to this day. It offers the quintessential blend of

  

  Danielle Sevier

  Compass Greater NY, LLC

  (845) 436-3857

  12 Tinker St, 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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  /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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  /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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  /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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  /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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  /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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  /42

  $1,495,000

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

  96 Meads Mountain Rd, Woodstock, NY 12498

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

  Lisa Halter HALTER ASSOCIATES REALTY INC

  96 Meads Mountain Rd, Woodstock, NY 12498
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  /28

  $1,225,000

  • 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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  /56

  $899,000

  • 4 Beds
  • 3 Baths
  • 2,125 Sq Ft

  48 Cooper Hollow Rd, 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 Rd, Bearsville, NY 12409
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  /32

  $845,000

  • 4 Beds
  • 2.5 Baths
  • 1,860 Sq Ft

  1531 Glasco Turnpike, Saugerties, NY 12477

  Rebuilt with care and vision, this 4-bedroom, 2.5-bathroom home on 2 private, wooded acres feels like a brand-new home—just minutes from both Woodstock and Saugerties. Tucked away from the road for total privacy yet close to shopping, dining, outdoor adventures, and the NY Thruway, this move-in-ready gem blends peaceful living with unmatched convenience.A full head-to-toe renovation has

  Baris Demirel Serhant LLC

  1531 Glasco Turnpike, Saugerties, NY 12477
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  /42

  $899,000

  • 4 Beds
  • 3 Baths
  • 1,456 Sq Ft

  40 Maxs Place, Kingston, NY 12401

  Tucked away on a quiet private road, this exceptional property offers a rare blend of privacy, style, and resort-like amenities—all just minutes from Woodstock and the best of the Catskills. At the heart of this beautifully updated home is a truly remarkable feature: a 40x60 indoor pool and sauna, creating an all-season sanctuary that's as perfect for quiet morning swims as it is for

  Leigh Wagner-Quintana Keller Williams Realty HV Nort

  40 Maxs Place, Kingston, NY 12401
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  /44

  $1,799,500

  • 5 Beds
  • 6 Baths
  • 6,164 Sq Ft

  174 Bristol Hill Rd, Glenford, NY 12433

  Beautiful spacious Contemporary. Soaring living room with custom fireplace. Interior renovation in 2019 includes Brazilian Walnut flooring, mix of oak and hickory. recent furnace and hot water tank. New windows, doors and roof as well as update lighting (2) 200 amp electric. Gourmet kitchen includes high end energy star appliances. Sauna. Seasonal Reservoir views.

  Thomas Pignone Green Ventures Realty

  174 Bristol Hill Rd, Glenford, NY 12433
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  /33

  $729,000

  • 2 Beds
  • 2 Baths
  • 1,565 Sq Ft

  28 Pine Grove St, Woodstock, NY 12498

  Nestled in the heart of the Village of Woodstock, this enchanting cottage awaits your arrival. Just a block from exquisite restaurants and vibrant shopping, it graces an oversized corner lot, providing a sense of space in its beautifully landscaped, fully fenced yard.With two generous bedrooms and two full bathrooms, the home invites you into an extended living area that radiates warmth

  Sheena Lepez Compass Greater New York, LLC

  28 Pine Grove St, Woodstock, NY 12498
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  /55

  $679,000 Open Sat 11AM - 1PM

  • 2 Beds
  • 2 Baths
  • 1,350 Sq Ft

  1338 Glasco Turnpike, Saugerties, NY 12477

  Welcome to an exquisite sanctuary nestled on a tranquil 1.8 acre lot at 1338 Glasco Turnpike, Saugerties, NY. This stunning home was built in 1935 and has been immaculately maintained and updated with modern luxury in mind.Upon entering, you are greeted by an incredible, fully furnished, two-bedroom, two-bathroom home with a brand new gourmet kitchen containing top-of-the-line appliances,

  Benjamin Armento Coldwell Banker Village Green

  1338 Glasco Turnpike, Saugerties, NY 12477
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  /26

  $479,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 1 Bath
  • 1,124 Sq Ft

  14 Goat Hill Rd Unit 15, Saugerties, NY 12477

  Welcome to your dream home, nestled in the serene landscape that perfectly balances country charm with modern convenience. This beautifully revamped house is an ideal retreat for anyone seeking a move-in ready haven, boasting a single-level living experience that caters to comfort and accessibility. As you step inside, you'll be greeted by a freshly painted interior that radiates warmth and

  Sara Gorman Maliha Coldwell Banker Village GreenK

  14 Goat Hill Rd Unit 15, Saugerties, NY 12477
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  /26

  $749,500

  • 3 Beds
  • 2.5 Baths
  • 2,450 Sq Ft

  94 Tanglewood Rd, West Hurley, NY 12491

  Set on 2.3 private acres in the heart of West Hurley, this spacious and light filled home offers a flexible layout with multiple living areas, and plenty of space to grow, both inside and out. Step inside to a generous entryway that opens into a living room / dining room area, perfect for entertaining. The well appointed kitchen features abundant cabinet space and sliding glass doors leading to

  Alyson Dugan Reidy Halter Associates Realty

  94 Tanglewood Rd, West Hurley, NY 12491
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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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  /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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  /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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  /29

  $799,000

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

  1521 Glasco Turnpike, Saugerties, NY 12477

  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, Saugerties, NY 12477
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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

  $990,000

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

  8 Pine Grove St, Woodstock, NY 12498

  Discover a rare investment opportunity in the vibrant enclave of Woodstock, NY with this impeccably restored, easy-to-show 1920s farmhouse located just minutes from the bus to NYC and Woodstock's iconic dining, shops, galleries, and live music. Freshly painted, with a new roof, this proven income-generating property offers reclaimed wide-plank pine floors, exposed beams, and curated designer

  Gary Heckelman Halter Associates Realty

  8 Pine Grove St, 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
• 

  

  /21

  $349,000

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  1055 Route 212, Saugerties, NY 12477

  Adorable getaway on 2 pretty acres. Light and bright ranch with open kitchen and living area with cozy wood stove. Two large bedrooms (one currently being used as a formal dining room). Separate oversized garage with electric. Conveniently located just minutes to the Saugerties and Woodstock Villages for shopping and restaurants. Three miles to the NYS Thruway exit 20.

  Bonnie Keegan Grist Mill Real Estate

  1055 Route 212, Saugerties, NY 12477
• 

  

  /25

  $625,000

  • 3 Beds
  • 2.5 Baths
  • 1,921 Sq Ft

  24 Normandy Ct, West Hurley, NY 12491

  Welcome to 24 Normandy, a spacious and inviting place to call home. Located just 2 miles to the heart of Village of Woodstock sited on a quiet cul de sac with private back yard with beautiful bluestone patio. This turn-key home has everything you have been looking for, generous living space offering both a living room and den with fireplace, a first floor bedroom suite, a renovated and updated

  Sheena Lepez Compass Greater New York, LLC

  24 Normandy Ct, West Hurley, NY 12491
• 

  

  /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
• 

  

  /32

  $399,500

  • 4 Beds
  • 1.5 Baths
  • 1,440 Sq Ft

  43 Brittany Dr, West Hurley, NY 12491

  Classic Colonial Charm in Prime LocationFirst time on the market in decades. This lovingly maintained and stately Colonial sits on over half an acre just minutes to the heart of the Village of Woodstock. A perfect blend of tranquility and convenience.From the moment you arrive the curb appeal is apparent, with its expansive front lawn, mature trees and its timeless architecture.

  Marcia Weiss Halter Associates Realty

  43 Brittany Dr, West Hurley, NY 12491
• 

  

  /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

  Gary DiMauro Four Seasons Sotheby's Int'l-K

  128 Newcut Rd, Bearsville, NY 12409

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