Olive, NY Homes for Sale

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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
• 

  

  

  /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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  /63

  $9,500,000

  • 6 Beds
  • 4.5 Baths
  • 6,284 Sq Ft

  197-199 Chestnut Hill Rd, Stone Ridge, NY 12484

  Discover one of the Hudson Valley's most remarkable properties—a 90-acre private estate in coveted Stone Ridge where curated landscapes, architectural charm, and world-class amenities converge to create an unparalleled retreat. Designed for both refined living and unforgettable entertaining, this extraordinary compound feels more like a private resort than a residence. Approach the front gate and

  Richard Vizzini Corcoran Country Living

  197-199 Chestnut Hill Rd, Stone Ridge, NY 12484
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  /34

  $1,549,000 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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  /48

  $1,175,000

  • 4 Beds
  • 2.5 Baths
  • 2,500 Sq Ft

  4085 New York 28a, West Shokan, NY 12494

  Where the Hamptons Meet the Catskills: Thoughtfully Restored Farmhouse on 4 AcresDirectly across from the stunning and historic Ashokan Reservoir and set on four park-like acres with mountain views, this fully renovated farmhouse blends timeless country charm with breezy Hamptons elegance. Historic character meets modern comfort, creating a home defined by beauty, ease, and seamless

  Quinn Hagstrand BHHS HUDSON VALLEY PROP-WDST

  4085 New York 28a, West Shokan, NY 12494
• 

  

  /31

  $749,000

  • 3 Beds
  • 2 Baths
  • 1,364 Sq Ft

  650 Beaverkill Rd, Olivebridge, NY 12461

  Situated off the road and embraced by lush woods, this beautifully maintained contemporary home has been lovingly cared for by its sole owner. The freshly painted interior and newly refinished hardwood floors create a welcoming ambiance, enhanced by an abundance of natural light that fills the entire first floor throughout the day. The open floor plan is perfect for entertaining, featuring a cozy

  Danielle Marchisella The Kinderhook Group, Inc.

  650 Beaverkill Rd, Olivebridge, NY 12461
• 

  

  /22

  $925,000

  • 3 Beds
  • 2 Baths
  • 1,403 Sq Ft

  52 Aster Rd, Olivebridge, NY 12461

  The ultimate upstate escape is waiting for you at 52 Aster Road, Olivebridge, NY. A sanctuary of modern elegance and natural beauty, this exquisite property offers a harmonious blend of luxury and tranquility. Spanning just under 12 acres, this secluded haven backs up onto State Land, providing unparalleled privacy and a mystical ambiance.The residence features three spacious bedrooms

  Ashley Prather Corcoran Country Living

  52 Aster Rd, Olivebridge, NY 12461
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  /32

  $625,000

  • 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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  /52

  $789,000

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft

  323 Beaverkill Rd, Kingston, NY 12401

  Unique, Exciting, Warm and Inviting. Imagine a long winding driveway into your own private forested acreage with a Storybook Saltbox style home immersed in an abundance of magical perennial gardens and flowering trees enhanced with integrated rock walls, stepping stones and patio and Adirondack style arbors, all uniquely designed by the owner, a master landscaper & builder. All the gardens are

  Edwin Maldonado Howard Hanna Rand Realty

  323 Beaverkill Rd, Kingston, NY 12401
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  /31

  $645,000

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

  252 Upper Boiceville Rd, Boiceville, NY 12412

  OPEN HOUSE SATURDAY 9/13 FROM 11-1PM. 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

  Richard Greenspan Ruth Gale Realty

  252 Upper Boiceville Rd, Boiceville, NY 12412
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  /35

  $599,900

  • 6 Beds
  • 3 Baths
  • 3,059 Sq Ft

  1441 County Road 2, Olivebridge, NY 12461

  Welcome to 1441 County Road 2 in Olivebridge, NY—a beautifully renovated 6-bedroom, 3-bathroom home nestled on 2.32 acres in the heart of the Catskills. This spacious 3,059 sq ft retreat features a brand-new kitchen, three cozy fireplaces, a sun-drenched great room, and a primary en suite on the main floor. With three bedrooms on each level, a full walk-out basement, and a large deck over the

  Nicholas Cuomo Keller Williams Realty

  1441 County Road 2, Olivebridge, NY 12461
• 

  

  /31

  $649,500

  • 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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  /34

  $979,000 New Construction

  • 3 Beds
  • 2 Baths
  • 2,160 Sq Ft

  805 County Road 2, Accord, NY 12404

  *PUBLIC OPEN HOUSE 9/13 11AM-1PM* Another spectacular home just hit the market in the heart of the Catskills; The Black Diamond. Identified as Walnut Woods, this 2,160 square foot new construction home, boasts 3-bedrooms and 2-bathrooms. Its open concept, single level living space is exactly what you have been waiting for. Crafted and curated by Hamlet Builders, this model is nothing but a

  Zachary Jarvis Berkshire Hathaway Homeservice

  805 County Road 2, Accord, NY 12404
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  /22

  $189,000

  • Land
  • 5.7 Acres
  • $33,158 per Acre

  187 Rocky Mountain Rd, Rochester, NY 12446

  Build your dream home on this private 5.7-acre parcel, tucked away at the end of a quiet town road. Mostly wooded and filled with natural beauty, the property is highlighted by the Mettachahonts Creek winding through the middle, creating a peaceful, picturesque backdrop. With clearing, mountain views are possible, adding even more potential to this setting. For outdoor enthusiasts, the land

  Sally Sprogis Four Seasons Sotheby's Int'l R

  187 Rocky Mountain Rd, Rochester, NY 12446
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  /38

  $325,000

  • 2 Beds
  • 1 Bath
  • 1,204 Sq Ft

  50 Bell Ln, West Shokan, NY 12494

  Peaceful 2-Bedroom Home in West Shokan.Set on nearly an acre in the heart of Catskill Park at the foothills of Peekamoose Mountain, this 2-bedroom, 1-bath home combines comfort, character, and natural beauty - fully move-in ready with thoughtful updates throughout. Inside, you'll find newly refinished hardwood floors, fresh paint, and a functional kitchen with brand-new appliances plus a new

  Amy Owens Coldwell Banker Village Green

  50 Bell Ln, West Shokan, NY 12494
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  /8

  $79,000

  • Land
  • 0.78 Acre
  • $101,282 per Acre

  0 Deerfield Rd Unit 20254253, Boiceville, NY 12412

  Rare lot in Boiceville with sewer connection available. This is a lightly wooded lot on a quiet dead end street but yet walking distance to Onteora High School, local supermarket, bus route, pharmacy, liquor store and Convenient Mart Gas Station and the Boiceville Rail Trail. Come take a look. The lot is near the end of the dead end so rarely any traffic. Boiceville has a lot to offer in this

  Siobhan Scanlan Win Morrison Realty-K

  0 Deerfield Rd Unit 20254253, Boiceville, NY 12412
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  /27

  $219,000

  • 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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  /42

  $2,399,000

  • 2 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  202 Dancing Rock Rd, Shokan, NY 12481

  Bathed in natural light and defined by expansive, uninterrupted panoramic reservoir and mountain views, this bold and award-winning modernist retreat is a masterpiece of clean, contemporary design. Set on 5 private, fenced and gated acres this 3,000 sq. ft. 2BD/2BA home (which can easily flex to 3BD) is surrounded by forever-wild land, offering total privacy and a profound connection to

  Joseph Satto Compass Greater NY, LLC

  202 Dancing Rock Rd, Shokan, NY 12481
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  /24

  $565,000

  • 6 Beds
  • 6 Baths
  • 1,025 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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  /27

  $375,000

  • 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 1 bedroom and 1 bath plus an office; 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

  Beth Alfeld Keller Williams Realty HV Nort

  2914 New York 28, Shokan, NY 12481
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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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  /49

  $550,000

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

  58 Kelder Hwy, Olivebridge, NY 12461

  Tucked in the heart of the Catskills, this meticulously maintained property is a private retreat where every detail has been thoughtfully designed for comfort, beauty, and enjoyment. Surrounded by lush, mature landscaping, the home's outdoor spaces are truly extraordinary—swim in the sparkling pool, entertain on the expansive patio with wet bar, rinse off in the outdoor shower, or simply relax

  Jeanne Boice Howard Hanna Rand Realty

  58 Kelder Hwy, Olivebridge, NY 12461
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  /25

  $349,999

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

  3076 New York 28, Shokan, NY 12481

  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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  /24

  $495,000

  • 2 Beds
  • 1 Bath
  • 1,388 Sq Ft

  44 Sheldon Hill Rd, Olivebridge, NY 12461

  As you enter the property your first impression will be of the abundance of plants organized into sections by the antique split-rail fencing. Then in front of you is a huge barn-style building and to your right is the ranch home. Rustic charm screams from every angle: The barn has 3 horse stalls on the right side, flanking a large central garage. On the left side is a workshop. All of this

  Yvonne Wilder Four Seasons Sotheby's Int'l R

  44 Sheldon Hill Rd, Olivebridge, NY 12461
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  /30

  $400,000

  • 2 Beds
  • 1 Bath
  • 876 Sq Ft

  4618 Atwood Rd, Stone Ridge, NY 12484

  Charming two-bedroom cottage, tucked along a country road, just minutes from the heart of Stone Ridge, NY. This sunny and well maintained two-bedroom, one-bath cottage offers a perfect blend of charm, comfort, and convenience in the Hudson Valley. Step inside to find an inviting eat-in kitchen anchored by a cozy woodstove—ideal for gathering on cool evenings and adding warmth and character to the

  Eric Bean Coldwell Banker Village Green

  4618 Atwood Rd, Stone Ridge, NY 12484
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  /25

  $550,000

  • 4 Beds
  • 1.5 Baths
  • 2,136 Sq Ft

  174 Palentown Rd, Kerhonkson, NY 12446

  They don't build them like this anymore! This home is a testament to quality craftsmanship, featuring a sturdy stone foundation, a charming brick exterior on the first floor, and floor joists that are practically tree-sized beams. With beautiful Swiss Chalet-style influences in the intricate railings and unique woodwork, plus custom built-ins throughout, this house is as solid and charming as

  Heather Hughes

  174 Palentown Rd, Kerhonkson, NY 12446
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  /20

  $189,900

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

  TBD Bostock Rd, Shokan, NY 12481

  This nearly 3 acre parcel of land is located in the countryside of Shokan NY on a quiet country road at the foothills of the Catskill Mountains. Let your imagination run wild with this level and partially wooded property. Electric is at the road and this parcel may also fit into the future Shokan Sewer District.

  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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  /39

  $2,995,000

  • 4 Beds
  • 4.5 Baths
  • 4,167 Sq Ft

  245 Brown Rd, Olivebridge, NY 12461

  Welcome to Bucky’s Pond. A long, private driveway lined with tall pines and mountain laurel leads you to this newly built home, sited on ten acres with a beautiful pond. The single story home is the latest project from renowned Bone Hollow Studio, expertly sited with no neighbors in sight. It is NorCal meets Hudson Valley, it is 4,100+ square feet of polished living space. With a sparkling

  Annabel Taylor Four Seasons Sothebys Intl

  245 Brown Rd, Olivebridge, NY 12461
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  /25

  $499,000

  • 3 Beds
  • 3 Baths
  • 1,500 Sq Ft

  27 Crosswell Manor Dr, Shokan, NY 12481

  Bright loft-style retreat with studio potential in low-tax Olive. Spacious and light, this open concept home is perfect for weekend escapes and full-time enjoyment. Set in a semi-private location with potential for lovely views with some selective cutting, the layout features Great rooms on both levels , ideal for live/work use, entertaining or a creative retreat. Upstairs,

  Laura Prince Hudson Dwellings Realty

  27 Crosswell Manor Dr, Shokan, NY 12481
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  /21

  $515,000

  • 2 Beds
  • 1 Bath
  • 1,251 Sq Ft

  183 Mill Rd, Olivebridge, NY 12461

  Nestled in the Catskill Mountains on 2.2 private acres, this fully renovated 2-bedroom, 1-bath home offers the ideal retreat. Enjoy serene woodland views from the back porch or relax inside with cathedral ceilings and abundant natural light. The home boasts all-new plumbing and electric, a modern kitchen with custom wood cabinetry, quartz countertops, and high-end stainless appliances. Hardwood

  Michael Bussa K. Fortuna Realty, Inc.

  183 Mill Rd, Olivebridge, NY 12461
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  /61

  $849,000

  • 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

  Siobhan Scanlan Win Morrison Realty-K

  258 Watson Hollow Rd, West Shokan, NY 12494
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  /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
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  /9

  $75,000

  • Land
  • 1 Acre
  • $75,000 per Acre

  14 Saw Pitt Rd, Kerhonkson, NY 12446

  Discover a rare opportunity to own a private getaway tucked inside Camp Adventure! This beautiful 1-acre wooded lot offers endless potential. Renovate or replace the 1960 seasonal cottage with a modern home and add a deck to fully enjoy the peaceful surroundings and natural beauty. Please use caution when entering the existing structure.The location is ideal for outdoor enthusiasts and those who

  Kristen Zigouras eXp Realty

  14 Saw Pitt Rd, Kerhonkson, NY 12446
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  /42

  $410,000

  • 2 Beds
  • 2 Baths
  • 1,196 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. Yard has beautiful

  Toni Scalici Asset Property Services

  2 Shokan Park Rd, Shokan, NY 12481
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  /30

  $1,175,000

  • 3 Beds
  • 2 Baths
  • 2,376 Sq Ft

  16 Blue Spruce Ln, Kerhonkson, NY 12446

  Enjoy smart living in this handcrafted, architect-designed modern cabin in sold-out Hudson Woods. Sited on 4.2 private acres with seasonal mountain views, this three-bedroom, two-bathroom residence blends modern design with natural materials for a timeless retreat in the woods. Walls of glass bring the outdoors in, filling the open-concept living space with light and offering a seamless

  Briana Cermak BHHS HUDSON VALLEY PROP-WDST

  16 Blue Spruce Ln, Kerhonkson, NY 12446
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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
• 

  

  /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
• 

  

  /56

  $525,000

  • 3 Beds
  • 3 Baths
  • 1,794 Sq Ft

  44 Dogwood Dr, Shokan, NY 12481

  Located in a highly desired part of the Catskill park! This home is perched on a hill with neighbors far enough away for your privacy, but close enough for security. Just minutes for the Ashokan reservoir, rail trail, skiing, hiking, fishing, Woodstock & Kingston. The home features a beautiful fireplace, pellet stove, hardwood floors, sauna, and lots of space to play or work from home. The large

  George Denise Keller Williams Realty HV Nort

  44 Dogwood Dr, Shokan, NY 12481
• 

  

  /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 weekend

  Paige McClintock Howard Hanna Rand Realty

  291 Acorn Hill Rd, Olivebridge, NY 12461

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