Olive, NY Homes for Sale

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  /50

  $595,000

  • 3 Beds
  • 3 Baths
  • 1,850 Sq Ft

  10 Old Farm Rd, Shokan, NY 12481

  Sited on a private 1.6-acre wooded corner lot in Shokan’s sought after Old Farm Estate, this serene and spacious contemporary Cape Cod blends comfort and style. The open concept living, dining, and kitchen areas flow easily to a partial wrap around deck—perfect for outdoor entertaining—with direct access to the ground level primary suite and hot tub. Upstairs, a super-sized guest suite features

  

  Leighton Ashley

  Coldwell Banker Timberland

  (845) 299-8073

  10 Old Farm Rd, Shokan, NY 12481
• 

  

  

  /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

  (845) 671-5010

  Tbd New York 28, Boiceville, NY 12412
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  /42

  $1,250,000

  $100K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  23 Traver Hollow Rd, Boiceville, NY 12412

  Custom-Built Modern Home with Dramatic Mountain Views There are homes with views - and then there are homes built for the view. Affectionately known as Mountain Thyme, the mountain is not simply a backdrop but the defining presence of the property. From the moment you arrive, it rises dramatically into view, close enough to feel immersive, yet expansive enough to inspire. Designed to showcase the

  

  Leigh Bokser

  Compass Greater NY, LLC

  (845) 609-1249

  23 Traver Hollow Rd, Boiceville, NY 12412
• 

  

  

  /42

  $574,999

  Coming Soon

  • 6 Beds
  • 2 Baths
  • 1,842 Sq Ft

  2 Mountain Valley Rd, Boiceville, NY 12412

  A rare and remarkable multi-family opportunity nestled in the heart of the Catskills — 2 Mountain Valley Road, Boiceville, New York presents two fully self-contained units, each delivering a level of space, privacy, and independence that is virtually unheard of in the multi-family market. Set against the stunning natural backdrop of Ulster County's Catskill Mountains, this 1,842 total square foot

  

  Richard Baxter

  Keller Williams Realty

  (845) 497-6342

  2 Mountain Valley Rd, Boiceville, NY 12412
• 

  

  

  /47

  $575,000

  Coming Soon

  • 6 Beds
  • 2 Baths
  • 1,842 Sq Ft

  2 Mountain Valley Rd, Boiceville, NY 12412

  A rare and remarkable multi-family opportunity nestled in the heart of the Catskills - 2 Mountain Valley Road, Boiceville, New York presents two fully self-contained units, each delivering a level of space, privacy, and independence that is virtually unheard of in the multi-family market. Set against the stunning natural backdrop of Ulster County's Catskill Mountains, this 1,842 total square foot

  

  Richard Baxter

  KELLER WILLIAMS REALTY

  (845) 957-7211

  2 Mountain Valley Rd, Boiceville, NY 12412
• 

  

  /34

  $1,990,000

  New Construction

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

  30 Narrow Rd, Kingston, NY 12401

  Welcome to Ashokan Forest Haven, a one-of-a-kind escape located between the heart of Stone Ridge and the Ashokan Reservoir. Constructed in 2024, the Haven is composed of clean lines, carefully considered finishes, and an ecological ethos creating a backdrop for adventurous, effortless living harmonized with its forest surroundings. This property can cater to a variety of lifestyles, whether

  

  Veronica Newton

  Compass Greater NY, LLC

  (329) 210-1502

  30 Narrow Rd, Kingston, NY 12401
• 

  

  /63

  $8,500,000

  $1M PRICE DROP

  • 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—an 80-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

  Richard Vizzini Corcoran Country Living

  197-199 Chestnut Hill Rd, Stone Ridge, NY 12484
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  /32

  $350,000

  • 2 Beds
  • 1.5 Baths
  • 1,055 Sq Ft

  32 Ridge Rd, Shokan, NY 12481

  Escape to the beauty of the Catskill Mountains in this cozy 2-bedroom, 1.5-bath home filled with rustic charm and full of warmth and character. The home features wide board plank floors, a charming loft area (perfect for guests or a creative workspace), and a classic brick fireplace that creates a cozy centerpiece for relaxing after a day outdoors.Step outside to enjoy the peaceful

  Joel Craig Coldwell Banker Village Green

  32 Ridge Rd, Shokan, NY 12481
• 

  

  /42

  $1,499,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,850 Sq Ft

  99 W Shokan Heights Rd, West Shokan, NY 12494

  Tucked into the rolling landscape of West Shokan, where seasonal Catskill Mountain views emerge through the trees, this new construction contemporary home offers a rare blend of modern craftsmanship, warmth, and quiet luxury across 4.25 private acres. Surrounded by forest and designed to embrace its natural setting, the home captures the essence of elevated country living--where refined interiors

  Richard Vizzini Corcoran Country Living

  99 W Shokan Heights Rd, West Shokan, NY 12494
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  /70

  $1,180,000

  Open Sun 11:30AM - 1:30PM

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

  10 Kolb Rd, Boiceville, NY 12412

  Dear buyer, I want you to know the story of this house. My family bought it three years ago and we did a total renovation to all the bathrooms and kitchen with new appliances and tile and all new fixtures. We also changed the back of the house and opened it up with a huge dormer facing the mountain since before the main view was to the expansive side meadow. We thought this was going to be our

  Jasmine Jordaan Halter Associates Realty

  10 Kolb Rd, Boiceville, NY 12412
• 

  

  /50

  $2,000,000

  $200K PRICE DROP

  • 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
• 

  

  /53

  $2,100,000

  • 4 Beds
  • 3 Baths
  • 5,199 Sq Ft

  250 Brodhead Rd, West Shokan, NY 12494

  A rare sanctuary where wellness, nature, and inspired country living converge across 17 idyllic acres. Framed by meadows, woodland, and a serene pond, the property offers a rare sense of escape--an immersive landscape designed as much for gathering and inspiration as for quiet retreat. At the heart of the grounds, the pond becomes a focal point for a lifestyle centered around wellness and

  Richard Vizzini Corcoran Country Living

  250 Brodhead Rd, West Shokan, NY 12494
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  /44

  $1,300,000

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

  95 Mill Rock Rd, Accord, NY 12404

  Set on a private road in the hamlet of Accord, Mill Rock Farmhouse is a modern, sun drenched home overlooking the Catskill Mountains, designed to balance privacy, nature, and modern convenience. Drive up the long, tree-lined driveway that opens to mountain views, a bluestone walkway, and thoughtfully upgraded landscaping that complements the natural surroundings. Enter the bright main floor with

  Antonia Gomez Country House Realty

  95 Mill Rock Rd, Accord, NY 12404
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  /6

  $725,000

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  720 Upper Cherrytown Rd, Kerhonkson, NY 12446

  To be built new construction by Cedar Development Group (@CedarDGHomes on IG). CDG uses fine finishes throughout and significant customization is possible with this home, or you can proceed with it as contemplated. Pictures are representative of another similarly completed house by CDG however exact finishes may vary and are subject to change or withdrawal. Home size can be augmented or reduced

  Ryan Scully Cedar Properties

  720 Upper Cherrytown Rd, Kerhonkson, NY 12446
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  /53

  $849,000

  • 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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  /24

  $649,000

  • 3 Beds
  • 2 Baths
  • 1,559 Sq Ft

  26 Krom Rd, Olivebridge, NY 12461

  Welcome to 26 Krom Rd in Olivebridge, a beautifully updated mid century ranch set against the rolling foothills of the Catskills. Offering over 1,500 square feet of thoughtfully designed living space, this 3 bedroom, 2 full bathroom home strikes the perfect balance between comfort, style and setting. Ideal as a full time residence or a weekend retreat, this property delivers easy living in one of

  Kristen Jock Compass Greater NY, LLC

  26 Krom Rd, Olivebridge, NY 12461
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  /50

  $1,750,000

  Open Sun 12PM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 4,103 Sq Ft

  16 Sahler Mill Rd, Olivebridge, NY 12461

  Set back down a long paved driveway, this property's picturesque setting provides complete privacy, breathtaking views and a tranquil atmosphere that truly defines country living at its finest. Discover the charm of this stunning 6 acre park-like property, featuring 3 ponds surrounded by stone walls (one with a timer-set fountain), meandering streams and frontage on the Rochester Creek. The

  Amy Levine Howard Hanna Rand Realty

  16 Sahler Mill Rd, Olivebridge, NY 12461
• 

  

  /78

  $1,750,000

  Open Sun 12PM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 4,103 Sq Ft

  16 Lower Sahler Mill Rd, Olivebridge, NY 12461

  Set back down a long paved driveway, this property's picturesque setting provides complete privacy, breathtaking views and a tranquil atmosphere that truly defines country living at its finest. Discover the charm of this stunning 6 acre park-like property, featuring 3 ponds surrounded by stone walls (one with a timer-set fountain), meandering streams and frontage on the Rochester Creek. The

  Amy Levine Howard Hanna Rand Realty

  16 Lower Sahler Mill Rd, Olivebridge, NY 12461
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  /50

  $875,000

  • 4 Beds
  • 3 Baths
  • 2,074 Sq Ft

  11 Blue Heron Dr, Kingston, NY 12401

  11 Blue Heron Drive, MarbletownFabulous 4-bedroom, 3-bath custom home set on 3.7 level acres just moments from the Ashokan Reservoir. Thoughtfully built in 1996 by a contractor for his own family, this residence offers quality craftsmanship and enduring comfort in a serene, natural setting. Privately sited on a quiet, tree-lined lot, the home overlooks a picturesque lagoon (not part of the

  Deb Dolan Keller Williams Upstate NY

  11 Blue Heron Dr, Kingston, NY 12401
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  /38

  $1,825,000

  New Construction

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

  20 Anderson Rd, Olivebridge, NY 12461

  Welcome to The Forest at Acorn Hill--a private sanctuary set deep within the natural beauty of the Catskills. Tucked away at the end of a quiet cul-de-sac, this exceptional property offers the rare balance of complete seclusion and effortless access to Woodstock, Kingston, and the coveted hamlets of Accord, Stone Ridge, and High Falls. An 850-foot approach winds through the landscape,

  Daniel Hauspurg Potter Realty

  20 Anderson Rd, Olivebridge, NY 12461
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  /69

  $1,200,000

  $95K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,955 Sq Ft

  269 Watson Hollow Rd, West Shokan, NY 12494

  Set in the quiet, storied hills of West Shokan, 269 Watson Hollow Road offers a rare blend of historic character and natural beauty. Originally constructed in the 1800s as a barn, this distinctive home was thoughtfully relocated across the stream approximately 40 years ago, where it now rests gracefully against the mountain backdrop.16.5 acres extend to the top of the ridge behind the house.

  Jeanne Boice Howard Hanna Rand Realty

  269 Watson Hollow Rd, West Shokan, NY 12494
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  /46

  $799,999

  $150K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,758 Sq Ft

  25 Old Farm Rd, Shokan, NY 12481

  This inviting country farmhouse-inspired home features 4 bedrooms and 2.5 baths, with all four bedrooms located on the second floor where original hardwood floors add warmth and character throughout. The primary suite includes an en-suite bath and three closets, while a finished walk-up attic with wide-plank floors and skylights offers flexible space for a studio, office, or guest area. The first

  Keely Vandebogart Halter Associates Realty

  25 Old Farm Rd, Shokan, NY 12481
• 

  

  /31

  $319,900

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

  1087 Samsonville Rd, Kerhonkson, NY 12446

  Charming Cape Cod set on 2 peaceful acres in the heart of the Hudson Valley! Located within the sought-after Rondout Valley Central School District, this 3-bedroom, 2 full bathroom home offers a wonderful opportunity to create your dream space.The spacious, well-maintained kitchen flows effortlessly into a large living room filled with natural light, creating a warm and inviting setting. A

  Maria Sairrino Cronin & Company Real Estate

  1087 Samsonville Rd, Kerhonkson, NY 12446
• 

  

  /5

  $67,500

  $8K PRICE DROP

  • Land
  • 14,374 Sq Ft
  • $204,545 per Acre

  1470 County Road 2, Olivebridge, NY 12461

  Looking to build a quaint, country escape on a low maintenance buildable lot? 1470 County Road 2 is the perfect location to do so! Equipped with a survey, BOH approval for a 2 bedroom home and zoning board of appeals approval from the local municipality, authorizes this lot as buildable for a 24x40 home. Bring your minimalistic 960 square foot country home to vision on this 0.44 acre lot in

  Zachary Jarvis BHHS Nutshell Realty

  1470 County Road 2, Olivebridge, NY 12461
• 

  

  /17

  $99,900

  $50K PRICE DROP

  • 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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  /35

  $599,900

  • 3 Beds
  • 3 Baths
  • 1,568 Sq Ft

  90 Jomar Ln, Olivebridge, NY 12461

  Welcome to 90 Jomar Lane, a spacious, move-in-ready ranch thoughtfully laid out for comfortable living. An additional 920 sq ft of living space is located in the fully finished basement and is not included in the 1,568 sq ft of the main level. This home features 3 bedrooms and 3 full bathrooms, and a large walk-up attic offering excellent storage or future potential. The primary bedroom opens to

  Chris Weber BHHS HUDSON VALLEY PROP-NP

  90 Jomar Ln, Olivebridge, NY 12461
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  /27

  $2,390,000

  • Land
  • 182.2 Acres
  • $13,117 per Acre

  Tbd Ryan Rd, Kerhonkson, NY 12446

  182 acres in Kerhonkson. Privacy, scale, beauty, and possibility in one rare piece of land. Tucked into the quiet landscape of Kerhonkson, this extraordinary 181-acre property offers the kind of space, privacy, and natural character that is almost impossible to find at this scale. Whether imagined as a secluded family compound, a private mountain retreat, or a thoughtful three-home development

  Kristian Unvericht Compass Greater NY, LLC

  Tbd Ryan Rd, Kerhonkson, NY 12446
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  /33

  $779,000

  $46K PRICE DROP

  • 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,

  Anne Hilton Purvis Coldwell Banker Village GreenN

  281 Dewitt Rd, Olivebridge, NY 12461
• 

  

  /25

  $589,000

  New Construction $14K PRICE INCREASE

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  349 High Point Mountain Rd, West Shokan, NY 12494

  Looking for an easy, simple move to the country? This is the one for you! This brand new construction, 2 bedroom 2 bath home offers easy living at its finest. Situated on 2.6 acres on a quiet country road, enjoy open concept living while bringing the outdoors in through the large sliding glass doors and windows. The main area of the home is perfect for entertaining with the high ceilings and

  Zachary Jarvis BHHS Nutshell Realty

  349 High Point Mountain Rd, West Shokan, NY 12494
• 

  /2

  $180,000

  • Land
  • 5.61 Acres
  • $32,086 per Acre

  00 Fischer Ln, Olive, NY 12461

  Location location location! This beautifully wooded lot is located on aprivate road with close proximity to Woodstock. Build your dream home or use it for your privacy buffer. and combine it with Kelder and 55 G Fischer for a total of 20 acres.

  Adrienne Volpe KW Mid-Hudson

  00 Fischer Ln, Olive, NY 12461
• 

  

  /12

  $224,999

  • 2 Beds
  • 1.5 Baths
  • 1,456 Sq Ft

  106 Sheldon Hill Rd, Olivebridge, NY 12461

  Investor opportunity in Olivebridge! Situated on 1.12 acres, 106 Sheldon Hill Road offers a 2-bedroom, 1.5-bath home with approximately 1,456 square feet of living space and a full unfinished basement, providing additional potential for storage or future expansion. Ideal for investors, contractors, or buyers looking for a renovation project in the Hudson Valley, this home presents a chance to

  Vincent Reda Keller Williams Realty

  106 Sheldon Hill Rd, Olivebridge, NY 12461
• 

  

  /17

  $315,000

  • 2 Beds
  • 1 Bath
  • 660 Sq Ft

  20 Kelder Rd, Olivebridge, NY 12461

  This charming Olivbridge cottage on a full acre is ideal as both a peaceful full-time residence or a perfect weekend escape. Step out onto the rear deck, which overlooks a serene, private green haven complete with its own organic garden. In the winter months, enjoy lovely seasonal views of Ashokan High Point. Conveniently located just minutes from the Ashokan Reservoir, the Ashokan Quarry Trail,

  June Mastropietro Mary Collins Real Estate, Inc

  20 Kelder Rd, Olivebridge, NY 12461
• 

  

  /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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  /49

  $550,000

  • 3 Beds
  • 2.5 Baths
  • 2,128 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
• 

  

  /13

  $229,888

  $80K PRICE DROP

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

  115 Acorn Hill Rd, Olivebridge, NY 12461

  Rare Turn-Key Development Opportunity in the Heart of the Catskills - Olive, NY GREAT FOR BUILDERS, DEVELOPERS & SAVVY INVESTORS!!!!! Two mobile homes on two separately deeded lots are being sold together as one exceptional package..... • Addresses: 115 & 117 Acorn Hill Rd, Olive, NY 12461 This prime offering features 2.04 acres of beautiful, usable land in a highly desirable residential area of

  Joseph Lombardo LOMBARDO HOMES & ESTATES

  115 Acorn Hill Rd, Olivebridge, NY 12461
• 

  

  /50

  $499,000

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

  252 Upper Boiceville Rd, Boiceville, NY 12412

  Set on a private, partially wooded one acre lot in Boiceville, this 3-bedroom, 2-bath home offers 1,924 square feet of flexible living space within the Onteora Central School District. Formerly an art gallery, the home combines architectural character, wooded surroundings, and a layout designed for both everyday living and entertaining. Oversized windows, skylights, and transom windows throughout

  Virginia Corbett eXp Realty

  252 Upper Boiceville Rd, Boiceville, NY 12412
• 

  

  /30

  $515,000

  • 2 Beds
  • 1 Bath
  • 1,251 Sq Ft

  183 Mill Rd, Olivebridge, NY 12461

  The perfect getaway from the hustle and bustle of the world. Nestled quietly in the Catskill Mountain Range, just minutes from the Ashokan Reservoir and a short drive away from Woodstock, Rosendale, Kingston, and New Paltz sits this lovely, renovated 2 bed, 1 bath home. On the property you'll find 2.2 acres of tranquility as you can look out the back windows at nearly all hours and see the

  Michael Bussa K. Fortuna Realty, Inc.

  183 Mill Rd, Olivebridge, NY 12461
• 

  /2

  $120,000

  • Land
  • 3.4 Acres
  • $35,294 per Acre

  00 Kelder Hwy, Olive, NY 12461

  Totally wooded and on a private road in a highly desirable area of Olive. Other lots available on this road as well.

  Adrienne Volpe KW Mid-Hudson

  00 Kelder Hwy, Olive, NY 12461
• 

  

  /49

  $570,000

  • 3 Beds
  • 2.5 Baths
  • 1,615 Sq Ft

  99 Wildflower Ln, Shokan, NY 12481

  Privately set on 5.6 acres in the heart of Olive, this distinctive home designed by renowned Woodstock architect Les Walker and built in 1985, the residence reflects a thoughtful contemporary vision with warm, livable spaces and a strong connection to the surrounding landscape. Ready for your own personal interior design upgrades. The main house features 1,615 square feet of unique living space,

  Baris Demirel Serhant LLC

  99 Wildflower Ln, Shokan, NY 12481
• 

  

  /50

  $849,000

  $26K PRICE DROP

  • 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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