Homes for Sale near Reginald Bennett Elementary School

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  /37

  $890,000

  • 3 Beds
  • 2.5 Baths
  • 2,184 Sq Ft

  2246 County Road 3, Olivebridge, NY 12461

  Nestled at the base of the Ashokan High Point mountain, one of the Catskills' most scenic peaks, this beautifully appointed, rustic 5.7-acre retreat is set back generously from a quiet country road just minutes from the Ashokan Reservoir. Custom built in 2000, the stylish, move-in-ready home features multiple great spaces for gathering with friends and family, both inside and out, starting with

  

  Hayes Clement

  Compass Greater New York, LLC

  (845) 456-9829

  2246 County Road 3, Olivebridge, NY 12461
• 

  Explore Reginald Bennett Elementary School

• 

  

  /2

  $229,000

  • 0.5 Baths
  • 4,173 Sq Ft

  8663 New York 28, Big Indian, NY 12410

  

  Elizabeth McGuire

  Listing by Keller Williams Upstate NY Properties

  (845) 516-9583

  

  8663 New York 28, Big Indian, NY 12410
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  /65

  $799,000

  • 3 Beds
  • 2 Baths
  • 2,196 Sq Ft

  26 Carle Rd, Mount Tremper, NY 12457

  Breathtaking mountain views set the stage at 26 Carle Rd in Mount Tremper, a custom 3-story Contemporary that truly reflects the spirit of the Catskills. With 3 bedrooms, 2 baths, and an open floor plan, the home offers both comfort and serenity. The centerpiece is a dramatic stone fireplace with a wood-burning insert, its chimney running through all three levels and filling the home with warmth

  

  Elizabeth 'Beth' Alfeld

  Keller Williams Realty HV Nort

  (845) 448-2157

  26 Carle Rd, Mount Tremper, NY 12457
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  /46

  $799,000

  • 3 Beds
  • 2 Baths
  • 2,196 Sq Ft

  26 Carle Rd, Mount Tremper, NY 12457

  Breathtaking mountain views set the stage at 26 Carle Rd in Mount Tremper, a custom 3-story Contemporary that truly reflects the spirit of the Catskills. With 3 bedrooms, 2 baths, and an open floor plan, the home offers both comfort and serenity. The centerpiece is a dramatic stone fireplace with a wood-burning insert, its chimney running through all three levels and filling the home with warmth

  

  Elizabeth 'Beth' Alfeld

  Keller Williams Hudson Valley

  (845) 448-2330

  26 Carle Rd, Mount Tremper, NY 12457
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  /52

  $1,340,000

  • 2 Beds
  • 2 Baths
  • 1,560 Sq Ft

  66 Plochmann Ln, Woodstock, NY 12498

  So close yet so far away! Walk to town from your totally private and like-new timber frame home with soaring 23-foot ceilings and walls of windows to bring nature in. As you enter from one of Woodstock's most coveted roads, through the stately pillars, you will feel a sense of tranquility with nature on this 9.94-acre lot that is just a half mile from the village of Woodstock and less than a half

  Mercedes Ross Coldwell Banker Village Green

  66 Plochmann Ln, Woodstock, NY 12498
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  /50

  $2,200,000

  • 4 Beds
  • 3 Baths
  • 3,671 Sq Ft

  53 Freeman Avery Rd, Olivebridge, NY 12461

  An architectural gem tucked away on 40 acres of pristine forest, this striking 3,671-square-foot residence is a stunning fusion of modern architecture and natural beauty. Crafted by the acclaimed Resolution: 4 Architecture, incorporating all of their most coveted features that converge in this divine mid century modern design. Travel down the tree lined driveway past a cascading waterfall to a

  Richard Vizzini Corcoran Country Living

  53 Freeman Avery Rd, Olivebridge, NY 12461
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  /67

  $6,995,000

  • 9 Beds
  • 7 Baths
  • 8,479 Sq Ft

  1471 New York 28a, West Hurley, NY 12491

  Welcome to one of the most exceptional private estates in the Hudson Valley—a rare and breathtaking 115-acre estate overlooking the shimmering waters of the Ashokan Reservoir and framed by sweeping Catskill Mountain vistas. This once-in-a-generation offering comprises three distinct residences, three separately deeded parcels, extensive manicured trails, and an unmatched suite of amenities—all

  Richard Vizzini Corcoran Country Living

  1471 New York 28a, West Hurley, NY 12491
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  /36

  $925,000

  • 3 Beds
  • 2 Baths
  • 1,998 Sq Ft

  64 Lower Byrdcliffe Rd, Woodstock, NY 12498

  This historic Woodstock home, complete with a legal short-term rental license, is ready for its next chapter. Just a short distance from the iconic village green and the heart of Woodstock, this recently restored 1897 Arts and Crafts farmhouse offers both privacy and convenience on one of the town's most desirable streets - a truly rare combination that seldom becomes available. The charming

  Victoria Stent Coldwell Banker Village Green

  64 Lower Byrdcliffe Rd, Woodstock, NY 12498
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  /41

  $459,000

  • 2 Beds
  • 2 Baths
  • 1,337 Sq Ft

  230 McKenley Hollow Rd, Big Indian, NY 12410

  Upgraded 1950s Catskills Ranch with Modern Comfort & Mountain Charm.Discover this beautifully upgraded 1950s ranch home set on 2 serene acres in the heart of the Catskill Mountains — just 2.5 hours from NYC.This thoughtfully designed 2-bedroom, 2-bath home offers an inviting open living plan with cathedral ceilings, ceiling fans, bamboo floors throughout, creating a warm and airy

  Jeffrey Ashton Coldwell Banker Timberland Pro

  230 McKenley Hollow Rd, Big Indian, NY 12410
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  /31

  $525,000

  • 2 Beds
  • 2 Baths
  • 1,130 Sq Ft

  233 Wittenberg Rd, Bearsville, NY 12409

  Picture yourself in this charming 1940 cottage with a roaring fire in its fieldstone double-height fireplace. If that doesn't capture your heart, the open living and dining areas with birch beamed ceilings will. Large expanses of windows flood the space with light, adding more charm essential to modern living. A wonderfully convenient full bath with claw-foot tub adds to the easy living. The

  Henry Ford Coldwell Banker Village Green

  233 Wittenberg Rd, Bearsville, NY 12409
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  /34

  $1,299,000 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,960 Sq Ft

  584 Acorn Hill Rd, Olivebridge, NY 12461

  Nestled on 2.9 acres on a country road in Olivebridge, this newly constructed residence offers a harmonious balance of contemporary elegance and the beauty of nature. Spanning nearly 3,000 square feet, this thoughtfully crafted home features 3 bedrooms, 3.5 baths, and a flex space ideal for an office, studio, or den. Each space has been designed with meticulous attention to detail, keeping modern

  Richard Vizzini Corcoran Country Living

  584 Acorn Hill Rd, Olivebridge, NY 12461
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  /28

  $674,500

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

  50 Halcott Ridge Rd, Pine Hill, NY 12465

  With 847 square feet of finished basement and 300 square foot hot tub room, this is larger than at first glance it seems. It boasts complete privacy and beauty. 6 lovely meandering minutes off Route 28.This beautiful home has 1557 square feet of living space before accounting for the basement and hot tub room. Drive down a winding driveway to your completely private retreat. Enjoy the

  Karen Sullivan Coldwell Banker Village GreenK

  50 Halcott Ridge Rd, Pine Hill, NY 12465
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  /3

  $10,299,000

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

  0 Dug Hill Rd Unit KEY909201, Hurley, NY 12443

  Now on the market: one of the most significant undeveloped land holdings in Ulster County, stretching from Kingston to the Ashokan Reservoir. Spanning over 686 acres, this rare offering is set in the ideal location: right in the heart of the Rondout Valley and just 90 minutes from New York City. Perfectly positioned between Kingston, Accord, and Saugerties/Woodstock. Surrounded by protected state

  Emily Haas-Godsil McRee Compass Greater NY, LLC

  0 Dug Hill Rd Unit KEY909201, Hurley, NY 12443
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  /18

  $400,000

  • 3 Beds
  • 1 Bath
  • 1,299 Sq Ft

  455 Woodland Valley Rd, Phoenicia, NY 12464

  Tucked away in the serene and highly sought-after Woodland Valley neighborhood of Phoenicia, this charming 3-bedroom, 1-bath home is the ideal country escape. Whether you're craving weekend getaways or looking for your own peaceful haven, this cozy retreat offers the perfect mix of rustic charm and natural beauty. Step outside to the soothing sound of a stream that runs through your

  Teresa Falkowski Keller Williams Realty HV Nort

  455 Woodland Valley Rd, Phoenicia, NY 12464
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  /11

  $499,000

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

  Tbd Wardwell Ln, Woodstock, NY 12498

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

  Laurie Osmond BHHS HUDSON VALLEY PROP-WDST

  Tbd Wardwell Ln, Woodstock, NY 12498
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  /27

  $949,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 2,552 Sq Ft

  58 Jones Quarry Rd, Woodstock, NY 12498

  Set on over four acres just minutes from the heart of Woodstock, this contemporary retreat offers the perfect balance of modern living and a deep connection to nature. Thoughtfully designed for both comfort and flexibility, the home features three bedrooms and three bathrooms with a light-filled, open layout that encourages connection to the outdoors. The main level offers a full bathroom,

  Michelle Bergkamp William Pitt Sotheby's Interna

  58 Jones Quarry Rd, Woodstock, NY 12498
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  /40

  $750,000

  • 3 Beds
  • 1.5 Baths
  • 799 Sq Ft

  161 Pine Hill Rd, Pine Hill, NY 12465

  As featured on HBO Max’s Cabin Chronicles (Season 3, Episode 2), this exceptional mountain retreat in Shandaken, Ulster County, seamlessly blends modern design with cozy Catskills living. Thoughtfully crafted inside and out, every detail evokes calm, comfort, and a deep connection to the surrounding natural landscape. Offered fully furnished and turnkey, the home features 3 bedrooms and 1.5

  Terry Robison Douglas Elliman Real Estate

  161 Pine Hill Rd, Pine Hill, NY 12465
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  /17

  $149,900

  • 3 Beds
  • 1 Bath
  • 800 Sq Ft

  244 Upper Samsonville Rd, Olivebridge, NY 12461

  Perfect 1 acre Catskill Mountain property with old mobile home in need of total rehabilitation. No well or septic on site. No existing heat source.

  Timothy Ayers Berardi Realty

  244 Upper Samsonville Rd, Olivebridge, NY 12461
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  /25

  $575,000

  • 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
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  /12

  $299,888

  • 2 Beds
  • 2 Baths
  • 1,536 Sq Ft

  515 Acorn Hill Rd, Olivebridge, NY 12461

  GREAT FOR BUILDERS.....THIS IS 2 FUNCTIONING MOBILE HOMES ON 2 LOTS BEING SOLD TOGETHER. ADDRESSES ARE 115 AND 117 ACORN HILL RD..... COMBINED LOTS IS A TOTAL OF 2.4 ACRES OF BEAUTIFUL LAND IN THE HIGHLY DESIRED AREA OF CATSKILL.....THIS LAND GRANDFATHERED IN YOU CAN BUILD 3-4 HOMES, AND IT IS PERFECT FOR INVESTORS....1.5 MILLION DOLLAR HOMES ARE BEING BUILT ACROSS THE STREET AND ON THE SAME

  Joseph Lombardo Listing by Lombardo Homes & Estates

  

  515 Acorn Hill Rd, Olivebridge, NY 12461
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  /42

  $639,000

  • 5 Beds
  • 2.5 Baths
  • 1,939 Sq Ft

  83 Ratterman Rd, Woodstock, NY 12498

  It's a WINNER! This is truly a wonderful house in an excellent location! Surrounded by trees with a quiet, rural feel, yet walking distance to the Village of Woodstock, it's everything a Woodstock buyer is looking for! From the moment you step up to this charmer, you'll be welcomed by a wide, impressive Bluestone walkway to the Bluestone front porch where you can envision many peaceful hours

  Edwin Maldonado Howard Hanna Rand Realty

  83 Ratterman Rd, Woodstock, NY 12498
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  /41

  $779,000

  • 7 Beds
  • 5 Baths
  • 3,968 Sq Ft

  8643 New York 28, Big Indian, NY 12410

  Catskills Creekside Chalet – Big Indian, Minutes from Belleayre Ski weekends, summer hikes, and fireside nights all begin here at this nearly 4,000 sq ft retreat on 3.1 acres (two parcels included) with creek access. Just minutes from Belleayre Mountain, it’s a true Catskills playground — whether for private use, rental income, or multi-family gatherings. Host up to 20 guests with ease! Designed

  Leslie Hill Hudson Modern Co

  8643 New York 28, Big Indian, NY 12410
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  /33

  $779,000

  • Land
  • 8.18 Acres
  • $95,232 per Acre

  281 Dewitt Rd, Olivebridge, NY 12461

  ONE OF THE MOST SPECTACULAR WATERFALLS IN ULSTER COUNTY is front and center on this extremely rare and unusual land offering. The visual beauty of the waterfall, stream, cliffs and land is unparalleled. Calming audio of the waterfall and rushing Mettacahonts stream is 24/7 and year-round. Pulling into the circular driveway you are greeted by a master stone worker's hand-built raised garden bed,

  Hilton Purvis Coldwell Banker Village GreenN

  281 Dewitt Rd, Olivebridge, NY 12461
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  /14

  $399,000

  • 1 Bed
  • 1 Bath
  • 841 Sq Ft

  57 Ohayo Mountain Rd, Woodstock, NY 12498

  BACK ON THE MARKET! BUYER FINANCING FELL THROUGH All the charm and convenience of Woodstock village living! Adorable period bungalow moments from the center of Woodstock! This 1 BR, 1 BA charmer features an additional room/four-season sunroom, handsome masonry fireplace with wood stove and a river rock chimney, modern kitchen, a clawfoot tub, separate laundry area, and is nestled in a wooded,

  Laurie Osmond BHHS HUDSON VALLEY PROP-WDST

  57 Ohayo Mountain Rd, Woodstock, NY 12498
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  /33

  $1,888,000

  • Land
  • 60.94 Acres
  • $30,981 per Acre

  TBD Zena Rd, Woodstock, NY 12498

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

  Baris Demirel Serhant LLC

  TBD Zena Rd, Woodstock, NY 12498
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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 Find Advisors

  7376 New York 28, Shandaken, NY 12480
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  /21

  $625,000

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

  16 Moggre Rd, Chichester, NY 12416

  Completely renovated & rebuilt modular ranch home with 5 bedrooms, 3 full bathrooms and open concept. From the modern kitchen to the elegant new bathrooms, this home has it all. Outside you have a large composite deck that overlooks the private 1.1 acres with patio and firepit. Close to Belleayre, Hunter and Windham Mountains. The home can come fully furnished for the right price. Currently being

  Jamie Sittner Find Advisors

  16 Moggre Rd, Chichester, NY 12416
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  /37

  $695,000

  • 3 Beds
  • 2.5 Baths
  • 3,630 Sq Ft

  14 Park Rd, Chichester, NY 12416

  Nestled on a quiet street in the tiny rural hamlet of Chichester, this large contemporary Colonial redefines ''room in the country.'' Spanning 3,600 sq ft of gracious living space, the home features a massive lower level with a spacious den, kitchen, and full bath—perfect for recreation, guests, or flexible use. The main level offers seamless circular flow from the kitchen into the living room

  James Angelakis BHHS HUDSON VALLEY PROP-WDST

  14 Park Rd, Chichester, NY 12416
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  /23

  $450,000

  • 2 Beds
  • 1 Bath
  • 1,232 Sq Ft

  55 John St, West Hurley, NY 12491

  Nestled in the picturesque hamlet of West Hurley, New York, this charming residence offers a wonderful opportunity to embrace the tranquility and natural beauty of the Catskill Mountains. Situated in a beautiful neighborhood, this property provides a true escape while remaining conveniently located to local amenities.

  Alexander Rokicki Pennywise Properties

  55 John St, West Hurley, NY 12491
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  /2

  $29,000

  • Land
  • 0.38 Acre
  • $76,316 per Acre

  Lot 48 Garfield Rd, Shandaken, NY 12464

  Lot 48 on Garfield Road sits quietly where the Catskills stop feeling like a destination and start feeling like home. Zoned R1.5, this parcel offers a rare balance of flexibility and restraint—enough land to build comfortably while preserving the sense of space and privacy that draws people to Shandaken in the first place. From the road, the property feels understated, but once you step onto the

  Thomas Santore Coldwell Banker Realty

  Lot 48 Garfield Rd, Shandaken, NY 12464
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  /7

  $149,000

  29 Reservoir Rd, Shokan, NY 12481

  Property has a 3BR, 1bath house which needs complete Renovation or Demolition. BEING SOLD AS-IS This is an ideal quiet location just a few lots off route 28 and walkable to The Asokan Reservoir. Minutes from all services and shopping. Kingston and Woodstock are near-by. Onteora school system right down the road. Rail Trail around the corner. Live in a country location and work in Kingston with

  Faye Storms Ruth Gale Realty

  29 Reservoir Rd, Shokan, NY 12481
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  /15

  $575,000

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

  00 Lauren Ct, Woodstock, NY 12498

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

  Melissa Zoe Hirsch Coldwell Banker Village Green

  00 Lauren Ct, Woodstock, NY 12498
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  /43

  $950,000

  • 7 Beds
  • 3 Baths
  • 3,806 Sq Ft

  57 Birch Creek Rd, Shandaken, NY 12480

  Take a look at this 3800 sq ft 1800s home that has been renovated top to bottom. This home has 7 bedrooms, 3 full bathrooms and lots of room to roam with 1.36 acres. Outside you'll find a back deck, patio, firepit area and Birch Creek at the back of the property. The home can come fully furnished for the right price. Currently being used as a short term rental with a gross revenue of 113k+ in

  Jamie Sittner Find Advisors

  57 Birch Creek Rd, Shandaken, NY 12480
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  /42

  $899,000

  • 5 Beds
  • 2 Baths
  • 1,764 Sq Ft

  1311 Wittenberg Rd, Mount Tremper, NY 12457

  Set well back from the road behind a handsome gated entry, this modern Catskills hideaway delivers the privacy everyone wants and the volume everyone hopes for. The approach is long and quiet; the house reveals itself slowly—wrapped by trees, with sky above and room to breathe on 4.04 acres. Inside, an airy great room rises with high ceilings and broad windows that pull in daylight and treetops.

  WINTON MORRISON Win Morrison Realty - W

  1311 Wittenberg Rd, Mount Tremper, NY 12457
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  /32

  $575,000

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

  1626 County Road 2, Olivebridge, NY 12461

  Welcome to this fully renovated country ranch nestled in the scenic Hudson Valley! This charming 3-bedroom, 2-bathroom home offers 1,400 square feet of thoughtfully designed living space that perfectly balances warm and neutral tones with modern attributes. Enter through the covered rocking chair front porch into a mudroom offering plenty of space with a coat closet, and storage for other outdoor

  Zachary Jarvis Berkshire Hathaway Homeservice

  1626 County Road 2, Olivebridge, NY 12461
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  /39

  $899,000

  • 2 Beds
  • 2 Baths
  • 2,545 Sq Ft

  176 Silver Hollow Rd, Chichester, NY 12416

  Set privately on 13+ acres and bordered by protected New York State land, this Catskills contemporary offers over 500 feet of private creek frontage along Silver Hollow (Warner) Creek. A rare combination of privacy, scale, and natural beauty. From multiple rooms, the gentle flow of the creek can be heard, connecting the home to its serene surroundings. The 2,500+ square foot residence unfolds

  Jessica Brasseur Houlihan Lawrence Millbrook Of

  176 Silver Hollow Rd, Chichester, NY 12416
• 

  

  /53

  $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
• 

  

  /24

  $2,400,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,420 Sq Ft

  420 Wittenberg Rd, Bearsville, NY 12409

  Woodstock Custom Compound - Create your own private family compound on 2.44 serene acres in the Woodstock Hamlet of Wittenberg—an exceptional to-be-built offering that brings together architectural vision, artisan materials, and the craftsmanship of noted builder James Nelson. This unique project includes a three-bedroom, three-and-a-half-bath main residence, a one-bedroom guest house, and a

  Peter Cantine Halter Associates Realty

  420 Wittenberg Rd, Bearsville, NY 12409
• 

  

  /39

  $1,799,000

  • 6 Beds
  • 3.5 Baths
  • 3,023 Sq Ft

  2320 Glasco Turnpike, Woodstock, NY 12498

  For the first time in its history, this 12-acre family estate—designed, built, and cherished by a prominent Woodstock family—comes to market. It's a rare opportunity for the next generation to build their own private compound for extended family or multiple guests. The property boasts a babbling brook, waterfall, two vintage Woodstock cottages, and acres of woods to explore. Located less than a

  George Denise Keller Williams Realty HV Nort

  2320 Glasco Turnpike, Woodstock, NY 12498
• 

  

  /10

  $125,000

  • Land
  • 0.58 Acre
  • $215,517 per Acre

  5485 New York 212, Shandaken, NY 12480

  CAUTION ! The garage on the property has previously caught fire .Must be torn down .DO NOT ENTER THE GARAGE Prime Catskills Land Listing - HB Commercial/Residential ZoningPerfectly positioned in the heart of the Catskills, this 1⁄2+ acre parcel offers dream-worthy mountain views and unbeatable access to the region's most sought-after outdoor attractions. Whether you're planning a

  Stephanie Berryann United Real Estate HV Edge

  5485 New York 212, Shandaken, NY 12480

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