Olivebridge, NY Homes for Sale

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  /65

  $899,000

  • 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

  

  Elizabeth 'Beth' Alfeld

  Keller Williams Realty HV Nort

  (845) 448-2157

  26 Carle Rd, Mount Tremper, NY 12457
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  /46

  $899,000

  • 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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  /24

  $325,000

  • 3 Beds
  • 1 Bath
  • 1,113 Sq Ft

  2772 New York 28, Shokan, NY 12481

  This charming ranch in the heart of Shokan offers a bright and cozy living space that's easy to fall for. With 1,113 square feet, 3 bedrooms, and 1 bath, it's the perfect size for simple living, whether you're starting out or looking to scale down. Inside, you'll find beautiful hardwood floors throughout and a stone fireplace that anchors the living room with warmth and character. The galley

  

  Donna Brooks

  Compass Greater NY, LLC

  (845) 622-8031

  2772 New York 28, Shokan, NY 12481
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  /39

  $299,000

  • 2 Beds
  • 2 Baths
  • 1,916 Sq Ft

  2914 New York 28, Shokan, NY 12481

  Affordable Two-Family Opportunity in Shokan! Set on 2 acres with frontage along Route 28, this two-family home is ready for its next chapter. The first-floor unit features 2 bedrooms and 1 bath; the second-floor apartment includes 1 bedroom and 1 bath—ideal for extended family, rental income, or offsetting your mortgage. The property needs renovation, but the potential is real for first-time

  

  Elizabeth 'Beth' Alfeld

  Keller Williams Hudson Valley

  (845) 506-1533

  2914 New York 28, Shokan, NY 12481
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  /39

  $369,000

  • 3 Beds
  • 2 Baths
  • 1,873 Sq Ft

  18 Tonche Terrace, Shokan, NY 12481

  This home is being sold as is make offers accordingly, inspections for informational purposes only. Home needs updating and TLC. Commuter friendly close to NY State Thruway, minutes to Woodstock, NY and close to major ski areas. Full finished basement with many possibilties.

  

  Frank Tangredi

  Frank Tangredi Realty Company

  (845) 957-9903

  18 Tonche Terrace, Shokan, NY 12481
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  /48

  $699,000

  • 3 Beds
  • 2 Baths
  • 1,596 Sq Ft

  258 Watson Hollow Rd, West Shokan, NY 12494

  Spacious 3 bedroom home with breathtaking mountain views. Perched on a hill, this home offers panoramic mountain views and sits on 19.20 acres bordered by a serene stream. There is a front entrance to the home that brings you into the lower level foyer room with blue stone flooring.. On this level is a finished game room/ office space/TV room with plenty of finished space. You also have access to

  

  Win Morrison

  Win Morrison Realty

  (845) 506-1624

  258 Watson Hollow Rd, West Shokan, NY 12494
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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
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  /31

  $1,990,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,775 Sq Ft

  30 Narrow Rd, Kingston, NY 12401

  Discover minimalist modern luxury in this stunning new contemporary home, set on an expansive 7.3-acre private lot. Whether you're dreaming of a tranquil upstate retreat or a primary residence, this property offers the perfect sanctuary. The open-concept living space features soaring double-height ceilings, creating an inviting and airy atmosphere, while two breathtaking walls of windows provide

  

  Veronica Newton

  Compass Greater NY, LLC

  (845) 328-5883

  30 Narrow Rd, Kingston, NY 12401
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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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  /41

  $825,000

  • 3 Beds
  • 3 Baths
  • 1,895 Sq Ft

  345 Glenford Wittenberg Rd, Glenford, NY 12433

  Set on three wooded and landscaped acres in the heart of the Catskills, this beautifully designed home blends modern comfort with timeless country charm. Offering 3 bedrooms, 3 bathrooms, including an attached ADU, the property is ideal for multi-generational living, guest accommodations, or additional rental income. Make your way to the top of the long tree lined driveway to be greeted by the

  Richard Vizzini Corcoran Country Living

  345 Glenford Wittenberg Rd, Glenford, NY 12433
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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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  /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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  /42

  $699,000

  • 4 Beds
  • 3 Baths
  • 1,952 Sq Ft

  4723 State Route 213, Olivebridge, NY 12461

  Opportunity Awaits! Two Homes with stunning, panoramic mountain views on 4.88 Acres.This unique and private property in Olivebridge features two separately deeded homes situated on a combined 4.88 acres, offering sweeping, unobstructed views of Ashokan High Point, Slide and the surrounding Catskill Mountains. From nearly every angle, the landscape stretches out before you, creating a peaceful

  Amy Owens Coldwell Banker Village Green

  4723 State Route 213, Olivebridge, NY 12461
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  /35

  $629,900

  • 3 Beds
  • 1 Bath
  • 1,930 Sq Ft

  5030 State Route 213, Olivebridge, NY 12461

  Privacy and seclusion await at this inviting retreat set on 1.10 acres along a quiet country road. A charming rocking-chair front porch welcomes you into the foyer and sets the tone for the warmth found throughout the home. Offering three bedrooms and one full bath, the layout provides comfort and ease for everyday living. The family room flows seamlessly into the living room and the eat-in

  Megan Rios Berardi Realty

  5030 State Route 213, Olivebridge, NY 12461
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  /33

  $1,295,000

  • 3 Beds
  • 2 Baths
  • 1,646 Sq Ft

  2372 County Road 3, Olivebridge, NY 12461

  Welcome to Bluestone Cove, a modern cabin tucked away on over 20 wooded acres in the heart of Olivebridge — where state-of-the-art construction meets the quiet rhythm of nature. Finished in 2022 on the site of a former bluestone quarry, this contemporary retreat balances strength, sustainability, and serenity in every detail. The exterior is clad in Nakamoto Wood's shou sugi ban Japanese cypress

  Briana Cermak BHHS HUDSON VALLEY PROP-WDST

  2372 County Road 3, Olivebridge, NY 12461
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  /29

  $975,000

  • 3 Beds
  • 2.5 Baths
  • 3,033 Sq Ft

  48 Hillside Dr, West Shokan, NY 12494

  Secluded Luxury Log Home with Spectacular Ashokan Reservoir ViewsWelcome to your dream retreat in the heart of the Catskills. Nestled on a private, serene hillside overlooking the stunning Ashokan Reservoir, this impeccably built 2006 log home combines rustic charm with modern luxury and energy efficiency.Crafted with top-of-the-line mechanicals and highly efficient flat-interior

  Mark Kanter BHHS HUDSON VALLEY PROP-WDST

  48 Hillside Dr, West Shokan, NY 12494
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  /51

  $1,325,000

  • 3 Beds
  • 3.5 Baths
  • 3,581 Sq Ft

  483 Acorn Hill Rd, Olivebridge, NY 12461

  Lean into Catskills living at your stylish country retreat on Acorn Hill Road. Built in 2022, this home is equal parts sanctuary and gathering place. Mornings begin on the wide front porch with coffee and crossword puzzle in hand. Afternoons spill onto the back deck, overlooking an expansive lawn framed by timeless stone walls. The lush backyard is the perfect place for games, gardening, and

  Laurel Sweeney Berkshire Hathaway Homeservice

  483 Acorn Hill Rd, Olivebridge, NY 12461
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  /31

  $645,000

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft

  110 Brown Station Rd, Olivebridge, NY 12461

  Escape to this beautifully updated 3-bedroom, 2-bath Cape home located in the heart of Olive Bridge. Set on a generous lot, the residence blends modern comfort with rustic charm. Inside, you'll find beamed ceilings and elegant hardwood floors throughout, enhancing the spacious layout that's perfect for both relaxation and entertaining. The first floor features a large living/dining area, a full

  Megan Rios Berardi Realty

  110 Brown Station Rd, Olivebridge, NY 12461
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  /42

  $949,000

  • 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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  /45

  $1,495,000

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

  174 Bristol Hill Rd, Glenford, NY 12433

  Secluded 6-Bedroom Estate with Seasonal Reservoir Views and Stunning Sunrises !sauna, reservoir view, Woodstock, luxury kitchen, elevator shaft, accessibility and grand staircase Nestled on a quiet, picturesque road just 4 miles from the heart of Woodstock, this extraordinary 6-bedroom, 6-bathroom estate offers privacy, craftsmanship, and timeless character on nearly 2 acres of lush, serene

  Thomas Pignone Green Ventures Realty

  174 Bristol Hill Rd, Glenford, NY 12433
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  /62

  $699,000

  • 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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  /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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  /3

  $215,000

  • Land
  • 1.6 Acres
  • $134,375 per Acre

  48 Ridge Rd, Shokan, NY 12481

  Discover the perfect blend of rural charm and convenience with this mostly level parcel in the Town of Olive. A municipal sewer system is scheduled for construction within the next year, adding future value and ease for development. Located just 4 minutes from Shokan and only 12 miles from Exit 19 on the NYS Thruway, you'll enjoy quick access to Kingston in about 15 minutes and the vibrant

  Julie Ronda BHHS HUDSON VALLEY PROP-NP

  48 Ridge Rd, Shokan, NY 12481
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  /57

  $529,000

  • 2 Beds
  • 2 Baths
  • 1,526 Sq Ft

  88 Burgher Rd, West Shokan, NY 12494

  Nestled in the Catskill Mountains, the small Hamlet of West Shokan sits in Watson Hollow at the base of South Mountain and Samuels Point where the Bushkill and Drybrook converge and enter into the picturesque Ashokan Reservoir. This beautiful little town is bordered by the vast acreage that surrounds the reservoir and has retained its rural character and charm for generations. On the approach to

  Edwin Maldonado Howard Hanna Rand Realty

  88 Burgher Rd, West Shokan, NY 12494
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  /23

  $415,000

  • 3 Beds
  • 2 Baths
  • 1,625 Sq Ft

  74 Upper Boiceville Rd, Boiceville, NY 12412

  Welcome to your fully reimagined 2025 Catskills retreat—move-in ready the moment you turn the key. This light-filled home has been updated top to bottom: energy-efficient windows, updated electric and plumbing, mini-split climate control, on-demand hot water, newer roof and a whole-house generator that keeps the lights on no matter what. Inside, fresh flooring, crisp paint, new trim and doors

  Dustin Leibowitz eXp Realty

  74 Upper Boiceville Rd, Boiceville, NY 12412
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  /14

  $350,000

  • Land
  • 2.7 Acres
  • $129,630 per Acre

  679 Vly Rd, Stone Ridge, NY 12484

  On a peaceful road in one of the most beautiful locations of the Vly in Stone Ridge. With Striking views and Wide Open Skies this property has hidden fern gardens, mature trees and bordered by stone walls. Lovely open meadows lead to your private forest to hike and explore. Pond site. An added advantage is that while the property has a Stone Ridge address it has Town of Olive taxes. Listing

  Bill Sidoriak Flemming Realty

  679 Vly Rd, Stone Ridge, NY 12484
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  /24

  $359,000

  • 2 Beds
  • 2 Baths
  • 1,587 Sq Ft

  143 Dubois Rd, Shokan, NY 12481

  Nestled atop a picturesque hill, this beautifully maintained home offers stunning seasonal views of the ridge behind. With freshly painted walls and refinished hardwood floors, the interior presents a neutral palette ready for your personal touch. This quality 1950s construction boasts generously sized bedrooms bathed in natural light, complete with large closets. A full bath conveniently located

  Danielle Marchisella The Kinderhook Group, Inc.

  143 Dubois Rd, Shokan, NY 12481
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  /6

  $289,000

  • Land
  • 3.2 Acres
  • $90,312 per Acre

  61 Hillside Dr, Olive, NY 12494

  --3 Acres with Mountain Views, Stream, and Ready-to-Build ImprovementsThis beautiful 3-acre parcel offers the perfect blend of light, privacy, and convenience. The land has been thoughtfully cleared and de-stumped, allowing sunlight to pour in while mature trees frame the property’s natural borders. A gentle stream runs along the western edge, with Hanover Mountain providing a striking

  Ellen Osgood Coldwell Banker Village Green

  61 Hillside Dr, Olive, NY 12494
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  /27

  $199,000

  • 2 Beds
  • 2 Baths
  • 1,668 Sq Ft

  340 Upper Boiceville Rd, Boiceville, NY 12412

  This is a ''Diamond in the Rough...Excellent potential to create a wonderful country home.Bring your vision, imagination and your contractor.Truly, an instance of ''Location, Location, Location.''Privately sited on 3.8 acres, in Low Tax Olive.Property includes some acreage across the road to insure privacy.

  Margo Obourn Win Morrison Realty - W

  340 Upper Boiceville Rd, Boiceville, NY 12412
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  /24

  $545,000

  • 6 Beds
  • 6 Baths
  • 2,050 Sq Ft

  2 Mountain Valley Rd, Boiceville, NY 12412

  Welcome to this exquisite two-family home nestled in the picturesque town of Olive. The upstairs apartment boasts charming cathedral ceilings and skylights, bathing the space in natural light and offering a sense of openness and serenity. Each of the spacious three-bedroom apartments, complete with a well-appointed bathroom, comes with its own garage for added convenience. Washer and dryer

  Barry Creagan Howard Hanna Rand Realty

  2 Mountain Valley Rd, Boiceville, NY 12412
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  /40

  $249,000

  • 1 Bed
  • 1 Bath
  • 1,100 Sq Ft

  62 Watson Hollow Rd, West Shokan, NY 12494

  Vintage 3-Season Cottage on the Bushkill Creek! Brimming with charm and potential, this beloved vintage cottage has been in the same family for over 50 years. Set on 1.4 park-like acres along the scenic Bushkill Creek, it offers a peaceful retreat with a touch of nostalgia. The large eat-in kitchen serves as a versatile gathering space, perfect for casual meals or creative projects. While the

  Ellen Osgood Coldwell Banker Village Green

  62 Watson Hollow Rd, West Shokan, NY 12494
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  /24

  $299,000

  • 3 Beds
  • 1.5 Baths
  • 2,520 Sq Ft

  3076 New York 28, Shokan, NY 12481

  A/O 11/25/2025 Nestled in the heart of the beautifully scenic Town of Olive, this spacious 3-bedroom, 2-bath home offers over 2,500 sq ft of potential just waiting for your vision and TLC. Set back on more than 3 peaceful acres with a serene stream running through the backyard, the property provides the perfect backdrop for a dream renovation or full-time retreat. Whether you're seeking a private

  Barry Creagan Howard Hanna Rand Realty

  3076 New York 28, Shokan, NY 12481
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  /20

  $189,900

  • Land
  • 2.6 Acres
  • $73,038 per Acre

  TBD Bostock Rd, Shokan, NY 12481

  The best of both worlds! Both private seclusion of living in the countryside, yet only seconds away from restaurants, shopping, major parks and emergency services! This rare opportunity of a beautiful, level, and ideally sized parcel in desirable Shokan. The perfect balance of flat cleared pasture and wooded wonderland with a year round stream. This dream parcel is nestled between Grant Averly

  Michael Lawlor Howard Hanna Rand Realty

  TBD Bostock Rd, Shokan, NY 12481
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  /11

  $749,900

  • Land
  • 27.9 Acres
  • $26,878 per Acre

  Tbd New York 28, Boiceville, NY 12412

  Incredible 27.9-acre development opportunity with mixed-use zoning and dual access from Route 28 and Upper Boiceville road. The front portion is zoned Highway Business with a 0.5-acre minimum, ideal for commercial use along this high-traffic corridor. The rear is zoned residential with a 1-acre minimum and could be subdivided for housing, a strip along the middle can go either way to be added to

  Teresa Falkowski Keller Williams Realty HV Nort

  Tbd New York 28, Boiceville, NY 12412
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  /50

  $2,500,000

  • 5 Beds
  • 3 Baths
  • 3,566 Sq Ft

  169 Baker Rd, West Hurley, NY 12491

  Set at the end of a long, private driveway, Eagle Ridge Estate sits high above the Ashokan Reservoir on over nine secluded acres, offering rare peace, unbroken mountain views, and the quiet grace of a home rooted deeply in history. Surrounded by century-old lilacs and a broad open lawn, this 5-bedroom, 3-bathroom residence spans 3,566 square feet across three floors, with timeless design and

  Jake Garay Serhant LLC

  169 Baker Rd, West Hurley, NY 12491
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  /33

  $625,000

  • 3 Beds
  • 2 Baths
  • 1,924 Sq Ft

  252 Upper Boiceville Rd, Boiceville, NY 12412

  This property is conveniently located between Woodstock and Phoenicia, This stunning .90 acre, 3bed/2bath renovated 2-story home with both floors having an open floor plan with skylights on the 2nd floor, transom windows, and has beautiful wood accents. The second floor has high ceilings, skylights and loft-like great room that showcase picturesque sunsets and mountain views. The first floor open

  Richard Greenspan Ruth Gale Realty

  252 Upper Boiceville Rd, Boiceville, NY 12412
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  /44

  $403,500

  • 2 Beds
  • 1.5 Baths
  • 1,525 Sq Ft

  2 Shokan Park Rd, Shokan, NY 12481

  Two bedroom, two bath ranch style home. Updates include brand new carpet, Vinyl plank flooring and some sheetrock. Home is freshly painted and just ready for you to move in. Home features floor to ceiling windows in the kitchen and living room. We are sure you will absolutely enjoy all the natural light all day long and watching all the changing of the seasons through them. Use your imagination

  Toni Scalici Asset Property Realty Services

  2 Shokan Park Rd, Shokan, NY 12481
• 

  

  /22

  $25,000

  • Land
  • 2 Acres
  • $12,500 per Acre

  Tbd New York 28, Oliverea, NY 12725

  2 Acres with Stream Access and Mountain Views - Big Indian, NY Discover a rare 2-acre parcel in the heart of the Catskill Mountains, offering raw natural beauty and boundless potential for the right buyer. Located just off the scenic Route 28 corridor in Big Indian (Town of Shandaken, Onteora School District), this wooded lot is surrounded by mountain ridgelines and bordered by the tranquil Birch

  Jeivan Castro Keller Williams Realty HV Nort

  Tbd New York 28, Oliverea, NY 12725
• 

  

  /30

  $1,175,000

  • 3 Beds
  • 2.5 Baths
  • 3,033 Sq Ft

  48 Hillside Dr, West Shokan, NY 12494

  Secluded Luxury Log Home with Spectacular Ashokan Reservoir Views + Additional ParcelWelcome to your dream retreat in the heart of the Catskills. Nestled on a private, serene hillside overlooking the stunning Ashokan Reservoir, this impeccably built 2006 log home combines rustic charm with modern luxury and energy efficiency.Crafted with top-of-the-line mechanicals and highly

  Mark Kanter BHHS HUDSON VALLEY PROP-WDST

  48 Hillside Dr, West Shokan, NY 12494
• 

  

  /7

  $110,000

  • Land
  • 2.6 Acres
  • $42,308 per Acre

  291 Acorn Hill Rd, Olivebridge, NY 12461

  Nestled off a private drive on Acorn Hill Road in the picturesque town of Olive, this 2.60-acre wooded lot offers the perfect blend of seclusion and natural beauty. Tucked away yet easily accessible via a deeded right of way, the property features stunning mountain views, rock outcroppings, and a peaceful, private setting surrounded by mature trees.Whether you're looking to build a serene

  Paige McClintock Howard Hanna Rand Realty

  291 Acorn Hill Rd, Olivebridge, NY 12461

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