Homes for Sale near Reginald Bennett Elementary 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 meticulously renovated 1900 carriage house. This exquisite 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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  /25

  $349,000

  • 2 Beds
  • 2 Baths
  • 848 Sq Ft

  442 Acorn Hill Rd, Olivebridge, NY 12461

  Charming & Updated 2-Bedroom Home in a Serene Country Setting. Discover this beautifully updated 2-bedroom, 2-bathroom home nestled in a private and peaceful location. With modernized electrical and mechanical systems, this home offers both comfort and reliability. The second-floor bathroom is brand new, adding a touch of luxury to the space. Step outside onto the lovely deck overlooking the

  

  Win Morrison

  Win Morrison Realty

  (845) 803-1710

  442 Acorn Hill Rd, Olivebridge, NY 12461
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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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  /41

  $2,400,000

  • 4 Beds
  • 3 Baths
  • 2,751 Sq Ft

  53 Freeman Avery Rd, Olivebridge, NY 12461

  Modern Marvel in Nature!! Perched atop a private 40-acre wooded sanctuary, this architecturally significant prefabricated modular home—designed by award-winning Resolution: 4 Architecture—offers a rare combination of design-forward living and immersive natural surroundings. Built in 2012 and spanning over 3,671 square feet, this four-bedroom, three-bathroom residence is a true retreat in the

  

  Michael Carr

  eXp Realty

  (845) 684-9454

  53 Freeman Avery Rd, Olivebridge, NY 12461
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  /47

  $799,000

  • 5 Beds
  • 4 Baths
  • 1,908 Sq Ft

  39 Van Wagner Rd, Willow, NY 12495

  Experience the epitome of country living with this historic farm home nestled in the heart of the Catskill Mountains. Whether you’re looking for your forever home, a weekend escape, or to start an Airbnb, this spacious home has it all! With nearly 2000 sqft of living space, this charming abode features a BRAND NEW METAL ROOF and GUTTERS, ALL NEW WINDOWS, 5 bedrooms and 3 full bathrooms, each

  Gina Nikola Keller Williams Valley Realty

  39 Van Wagner Rd, Willow, NY 12495
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  /50

  $4,999,000

  • 4 Beds
  • 4 Baths
  • 3,899 Sq Ft

  18 Striebel Rd, Woodstock, NY 12498

  Nestled in the heart of Woodstock, this extraordinary 70+ acre estate is a rare offering of artistic heritage, architectural beauty, and serene natural surroundings. Known as The Stone House on Striebel Road, this iconic bluestone compound has stood at the crossroads of music, literature, and counterculture for over a century.Built in 1914 as a country retreat, the main Stone House

  Michelle Bergkamp Corcoran Country Living

  18 Striebel Rd, Woodstock, NY 12498
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  /37

  $925,000

  • 7 Beds
  • 4.5 Baths
  • 3,775 Sq Ft

  28 Esopus Ave, Phoenicia, NY 12464

  At the entrance to Phoenicia's picturesque Woodland Valley you will find this amazing one of a kind compound. Current owners have lovingly maintained and renovated almost every part of the property. They have been living in the main house and running a thriving short-term rental business for the past 13 years and were featured in Curbed NY as one of the best vacation rentals in the Hudson Valley.

  Jasmine Jordaan Halter Associates Realty Inc.

  28 Esopus Ave, Phoenicia, NY 12464
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  /26

  $550,000

  • 3 Beds
  • 2.5 Baths
  • 1,400 Sq Ft

  58 Kelder Rd, Olivebridge, NY 12461

  This charming 3-bedroom, 2.5-bath home is nestled on 6.2 acres with picturesque mountain views abound. The home welcomes you with an inviting living area which opens up to the kitchen and dining area. Serving as the heart of the home, this thoughtful floor plan is ideal for gathering with loved ones or entertaining guests. The modern kitchen, with its sleek stainless steel appliances and ample

  Richard Vizzini Corcoran Country Living

  58 Kelder Rd, Olivebridge, NY 12461
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  /56

  $449,000

  • 3 Beds
  • 2 Baths
  • 1,779 Sq Ft

  49 Ulster and Delaware Turnpike, Big Indian, NY 12410

  Discover your dream ski home in a prime location minutes to Bellleayre Ski Center! This completely renovated 3-bedroom, 2-bathroom home offers the perfect blend of modern comfort and proximity to the slopes. Step inside to an open-concept living space designed for seamless entertaining and cozy gatherings. The centerpiece of the living area is an impressive floor to ceiling stone fireplace,

  Jeffrey Ashton Coldwell Banker Timberland Pro

  49 Ulster and Delaware Turnpike, Big Indian, NY 12410
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  /50

  $449,000

  • 3 Beds
  • 2 Baths
  • 1,779 Sq Ft

  49 Ulster & Delaware Turnpike, Shandaken, NY 12480

  Discover your dream ski home in a prime location minutes to Bellleayre Ski Center! This completely renovated 3-bedroom, 2-bathroom home offers the perfect blend of modern comfort and proximity to the slopes. Step inside to an open-concept living space designed for seamless entertaining and cozy gatherings. The centerpiece of the living area is an impressive floor to ceiling stone fireplace,

  Jeffrey Ashton Listing by Coldwell Banker Timberland Properties

  

  49 Ulster & Delaware Turnpike, Shandaken, NY 12480
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  /70

  $1,399,000

  • 3 Beds
  • 3 Baths
  • 3,392 Sq Ft

  544 Herdman Rd, Shandaken, NY 12480

  Welcome to The Big Red House, an oasis at the end of a private road surrounded by Mountain Views, a stream and open skies. This property has everything you would want. Hike along miles of hiking trails on your 35 private acres with state land abutting on two sides; or drop in on the custom made skateboard ramp; or maybe just relax and meditate listening to the sounds of the stream; or sit by your

  Jasmine Jordaan Halter Associates Realty

  544 Herdman Rd, Shandaken, NY 12480
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  /60

  $115,000

  • Land
  • 12 Acres
  • $9,754 per Acre

  00 Garfield Road Lot Unit WP001, Phoenicia, NY 12464

  Located just minutes off Route 28 in the hamlet of Phoenicia, this beautiful property offers great hunting and recreational opportunities. Access to this parcel is provided by an improved right-of-way (ROW). Leading to a place to park, for hunting, camping, hiking, or unloading your ATVs. Bordering state land on two sides further enhances the seclusion and privacy while giving you more land to

  Clint Carlson Whitetail Properties Real Estate

  00 Garfield Road Lot Unit WP001, Phoenicia, NY 12464
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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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  /43

  $699,000

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  68 Garfield Rd, Phoenicia, NY 12464

  WOODLAND VALLEY-PHOENICIAPEACEFUL COUNTRY SETTINGThis is PERFECT full-time or weekend home, with mountain views. Windows in all directions provide continuous daylight. Only a very short drive from Main Street, Phoenicia. It's a 1.13 Acre property that's high up with extensive underground drainage systems. It goes across Herdman Road and down a slope to the Esopus with a viewing

  Alfred Peavy Ruth Gale Realty

  68 Garfield Rd, Phoenicia, NY 12464
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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

  $699,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 1,839 Sq Ft

  10 Norman Rd, Shandaken, NY 12480

  Private Split Level on 3 AcresTucked away in a quiet, wooded setting, this 3-bedroom, 2.5-bath split level offers the perfect blend of privacy, natural beauty, and thoughtful design. Set on 3 acres and surrounded by mature trees, seasonal waterfalls, and perennial gardens, the property borders forever-wild state forest, with hiking trails woven throughout...a peaceful retreat ideal for

  Amy Owens Coldwell Banker Village Green

  10 Norman Rd, Shandaken, NY 12480
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  /38

  $749,000

  • 2 Beds
  • 2 Baths
  • 1,208 Sq Ft

  18 Country Club Ln, Woodstock, NY 12498

  Stunning reimagined Ranch, just 1/2 Mile from the Center of Woodstock, 2/10 of a Mile to the NYC Bus Route,yet providing an excellent sense of privacy, and a perfect rural setting.Beautifully, and thoughtfully updated baths and kitchen, embracing the best of Modern Design principals and practicality.The perfect country escape, yet within easy access to restaurants, shopping and

  Margo Obourn Win Morrison Realty - W

  18 Country Club Ln, Woodstock, NY 12498
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  /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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  /38

  $750,000

  • 3 Beds
  • 2.5 Baths
  • 1,557 Sq Ft

  50 Halcott Ridge Rd, Pine Hill, NY 12465

  Welcome to an amazing home embodying serenity itself, a fabulous and totally private contemporary home with multiple green features.Drive down a winding driveway to your completely private retreat. Enjoy the light-filled living space with French doors to a large deck. Enjoy your beverage in front of a magnificent stone fireplace as you drink in the tranquil view.Then head down to a

  Karen Sullivan Coldwell Banker Village GreenK

  50 Halcott Ridge Rd, Pine Hill, NY 12465
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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

  $1,400,000

  • 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

  $1,400,000

  • 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 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 PROP-WDST

  11 Grog Kill Rd, Willow, NY 12495
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  /24

  $875,000

  • 3 Beds
  • 2.5 Baths
  • 2,695 Sq Ft

  19 Jay St, Phoenicia, NY 12464

  An incredibly unique water front home in the cute town of Phoenicia. Located at the end of a quiet road on the outskirts of town with its shops within walking distance, and a quick 2 hour drive or a convenient bus ride from Manhattan. This is a perfect weekend house or a full time residence for a hybrid/remote worker, that allows for the best of both worlds: Access to convenience of the

  George Denise Keller Williams Realty HV Nort

  19 Jay St, Phoenicia, NY 12464
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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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  /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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  /50

  $875,000

  • 3 Beds
  • 2 Baths
  • 1,485 Sq Ft

  18 Jomar Ln, Olivebridge, NY 12461

  You'll understand just how special this 41 Acre property is once you arrive. Just driving down the country road to get here is already a treat. Situated at the base of the majestic High Point Mountain you'll find a private driveway that takes you through a beautiful forest and then it opens up to acres of your own open farmlands.....the open fields are perfectly suited to horses and with an

  Edwin Maldonado Howard Hanna Rand Realty

  18 Jomar Ln, Olivebridge, NY 12461
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  /40

  $675,000

  • 2 Beds
  • 2 Baths
  • 1,737 Sq Ft

  1521 Wittenberg Rd, Mount Tremper, NY 12457

  Welcome to 1521 Wittenberg Road – a serene and special retreat nestled in the heart of Mt. Tremper, just minutes from Phoenicia and a scenic 10-minute drive to Woodstock. This well-maintained 2-bedroom, 2-bathroom home offers the kind of peace and privacy that’s increasingly rare. Set on a lush lot with mature plantings, flowering dogwoods, blooming rhododendrons, and a small meandering

  Baris Demirel Serhant LLC

  1521 Wittenberg Rd, Mount Tremper, NY 12457
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  /29

  $675,000

  • 7 Beds
  • 4 Baths
  • 3,500 Sq Ft

  49 Highlands Rd, Highmount, NY 12441

  Historic Victorian Elegance with Unmatched Belleayre Mountain Views --Step into timeless grandeur at this stately Victorian estate, perched directly across from Belleayre Mountain with panoramic views of its iconic ski runs. Set on 2.65 serene acres, this 1900s home offers 3,500 square feet of refined character, featuring seven bedrooms and four bathrooms, including a versatile accessory

  Felicity Taylor Corcoran Country Living

  49 Highlands Rd, Highmount, NY 12441
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  /38

  $845,000

  • 4 Beds
  • 3 Baths
  • 3,123 Sq Ft

  46 Sylken Ln, West Hurley, NY 12491

  Tucked at the end of a quiet, private road in beautiful and convenient West Hurley, this generously sized home offers a blend of seclusion and accessibility that's hard to find. Set on over 2.5 acres and surrounded by nature, it's just 15 minutes to both Woodstock and Kingston, with the Ashokan Reservoir and countless other Catskills towns within easy reach. Inside, the layout is made for easy

  Briana Cermak BHHS HUDSON VALLEY PROP-WDST

  46 Sylken Ln, West Hurley, NY 12491
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  /43

  $1,450,000

  • 4 Beds
  • 6 Baths
  • 4,961 Sq Ft

  110 Lost Clove Rd, Big Indian, NY 12410

  Welcome to Lost Clove Mountain House, an idyllic hideaway in the heart of the Catskills with ample room to roam. Tucked away at the end of a quiet road and bordered by NY State land, this fully renovated property offers unmatched privacy and a front-row seat to Catskills beauty. The main house features four bedrooms, three full baths, two half baths, a striking stone fireplace, and a wall of

  Jessica Brasseur Houlihan Lawrence Inc.

  110 Lost Clove Rd, Big Indian, NY 12410
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  /56

  $825,000

  • 8 Beds
  • 4.5 Baths
  • 2,623 Sq Ft

  7376 New York 28, Shandaken, NY 12480

  Take a look at this 8 bedroom, 4 full bathroom home with 4 floors of living space along with 1.77 fenced in acres. Completely renovated with modern fixtures and amenities, nothing to do but move in or rent immediately. The outside of the property features a front porch, Tesla charging station, spacious back deck with pergola and hot tub, large open yard and firepit area. Located right down the

  Jamie Sittner Oxford Property Group USA

  7376 New York 28, Shandaken, NY 12480
• 

  

  /18

  $795,000

  • 1 Bed
  • 1 Bath
  • 604 Sq Ft

  8 Emerson Terrace, Shandaken, NY 12464

  Quintessential Catskill cabin on 38 picturesque acres of multi-tiered, terraced terrain with diverse rock features and stunning mountain views. Extensive stone work by longtime contractor-owner repurposing bluestone quarried on the property. Stone walls, an outdoor grilling station and amazing natural rock face of the mountain itself shape the central lawn of this alpine oasis. The owner-built

  Peter Cantine Halter Associates Realty

  8 Emerson Terrace, Shandaken, NY 12464
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  /37

  $720,000 Coming Soon

  • 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
• 

  

  /26

  $549,000

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft

  76 Firehouse Rd, Big Indian, NY 12410

  Modern 3 Bedroom, 2 Bath Ranch - Single Family Home, 3 Zone Radiant heated polished concrete floor, Open floor plan, Well lit by expansive 5 foot Anderson windows, Large Fireplace, MBR with ensuite and large walk in closet, Inviting covered porch, home is bordered by the picturesque Esopus Creek with fly fishing access, 1.22 Acre property, county road is well plowed, High quality custom home,

  Ralph Harvey ListWithFreedom.Com

  76 Firehouse Rd, Big Indian, NY 12410
• 

  

  /6

  $250,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,361 Sq Ft

  2 Lake St, Pine Hill, NY 12465

  Escape to your own creekside retreat in the Catskills!This fixer-upper in charming Pine Hill offers incredible potential and a picturesque setting. Imagine cozy evenings by Birch creek, with mountain views off your deck.Set on a dead-end street leading to Belleayre Lake, this 3-bedroom, 2-bathroom home features a detached 2-car garage and a private backyard with plenty of

  Einat Bar Compass Greater NY, LLC

  2 Lake St, Pine Hill, NY 12465
• 

  

  /21

  $675,000

  • 15 Beds
  • 15 Baths
  • 10,130 Sq Ft

  288-292 Main St, Pine Hill, NY 12465

  The Pine Hill Arms - a Catskills classic, ready for revival! Built in 1882 and set on nearly 2 acres in the heart of Pine Hill, this historic 15-bedroom inn with full-service restaurant, bar, and cafe offers a rare opportunity to reimagine a beloved Catskills institution. With a total interior square footage of over 10,000 sq ft, the property features a spacious lobby, commercial kitchen,

  Laura Warren Coldwell Banker Village Green

  288-292 Main St, Pine Hill, NY 12465
• 

  

  /56

  $355,000 Open Sat 12PM - 2PM

  • 2 Beds
  • 1.5 Baths
  • 1,324 Sq Ft

  18 Tremper Ave, Phoenicia, NY 12464

  Anchored in the vibrant heart of the Catskills Park, this traditional 1800s village home blends timeless character with thoughtful modern updates. Offering 2 bedrooms, 1.5 baths, and 1,324 sq ft of all-season comfort, the property features a well-tended backyard garden which is an oasis with perennials, mature shade trees and an inviting post-and-beam screened back porch perfect for seasonal

  Leighton Ashley Coldwell Banker Timberland

  18 Tremper Ave, Phoenicia, NY 12464

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