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Olive, NY Homes for Sale

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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

    Agent Photo

    Hayes Clement

    Compass Greater New York, LLC

    (845) 456-9829

    2246 County Road 3, Olivebridge, NY 12461
  • /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—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
  • /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
  • /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
  • /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
  • /12

    $269,888

    • 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
  • /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
  • /51

    $1,275,000

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

    483 Acorn Hill Rd, Olivebridge, NY 12461

    Set along quiet Acorn Hill Road, this thoughtfully designed Catskills retreat delivers a rare balance of privacy, polish, and everyday convenience. Built in 2022, the home feels intentionally set apart, a place where calm and comfort take center stage, while favorite destinations remain just minutes away. Life unfolds with ease here. Mornings begin on the wide front porch with coffee in hand,

    Emily Daniels Berkshire Hathaway Homeservice

    483 Acorn Hill Rd, Olivebridge, NY 12461
  • /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
  • /50

    $1,275,000

    • 3 Beds
    • 2.5 Baths
    • 2,181 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

    Emily Daniels BHHS Nutshell Realty

    483 Acorn Hill Rd, Olivebridge, NY 12461
  • /28

    $599,000 New Construction

    • 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 Berkshire Hathaway Homeservice

    349 High Point Mountain Rd, West Shokan, NY 12494
  • /18

    $2,650,000 New Construction

    • 4 Beds
    • 5 Baths
    • 2,625 Sq Ft

    131 Oakley Rd, Accord, NY 12404

    Tucked along a quiet bend in one of Accord's most picturesque country roads, this newly built residence feels like stepping into another era - one defined by timeless beauty, quietude, and a deep connection to the land. Sited on four private acres that blend open meadow and mature forest, the home is introduced by a long driveway that winds through the grassland, past a serene pond that borders

    Leslie Foti Coldwell Banker Village Green

    131 Oakley Rd, Accord, NY 12404
  • /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
  • /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
  • /58

    $1,700,000

    • 3 Beds
    • 2.5 Baths
    • 2,406 Sq Ft

    186 Vly Atwood Rd, Stone Ridge, NY 12484

    Welcome to Vly House, a striking modern chalet set into a natural stone ledge in the heart of enchanting Stone Ridge. Oriented toward the private pond and gently rolling wooded acreage, the home feels both grounded and expansive. A steep gabled form rises from the rock, dark and quiet against the woods, its disciplined gabled form clad in dark siding that recedes into the trees. Below, wide decks

    Angelica VonDrak Houlihan Lawrence-R

    186 Vly Atwood Rd, Stone Ridge, NY 12484
  • /33

    $569,000

    • 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
  • /44

    $385,000

    • 2 Beds
    • 2 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
  • /6

    $289,900

    • Land
    • 13.14 Acres
    • $22,062 per Acre

    252 Upper Samsonville Rd, Krumville, NY 12461

    The perfect Catskill Mountain homesite. Unimproved vacant land with existing pad for manufactured home. Gently sloping with views at the top of the property.

    Timothy Ayers Berardi Realty

    252 Upper Samsonville Rd, Krumville, NY 12461
  • /5

    $75,000

    • Land
    • 0.45 Acre
    • $166,667 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 and zoning board of approval from the local municipality authorizes this lot as buildable for a 24x40 home. With additional Board of Health approval for a 2 bedroom septic, bring your minimalistic 960 square foot country home to vision on this

    Zachary Jarvis Berkshire Hathaway Homeservice

    1470 County Road 2, Olivebridge, NY 12461
  • /50

    $875,000

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

    18 Jomar Ln, Olivebridge, NY 12461

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

    Edwin Maldonado Howard Hanna Rand Realty

    18 Jomar Ln, Olivebridge, NY 12461
  • /27

    $429,000

    • Land
    • 14.3 Acres
    • $30,000 per Acre

    239 Sundale Rd, Accord, NY 12404

    Stunning 14.3 Acres of Peace and Possibility in Accord, NY Set along a quiet country road, this exceptional 14.3-acre property offers wooded privacy, natural beauty, and endless potential. The gently sloping landscape leads down to a tranquil pond and a meandering stream, with moss-covered stone steps descending toward the water. From the road and fenced area, two original entry points remain:

    Jesse Marcus Habitat Real Estate Group

    239 Sundale Rd, Accord, NY 12404
  • /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
  • /18

    $349,000

    • 3 Beds
    • 2.5 Baths
    • 1,968 Sq Ft

    12 Fern Ln, Shokan, NY 12481

    Have you been looking for a Contemporary Home? Maybe you haven't found one that's right for you? Well here's your chance to make it perfect, exactly the way you want! This Contemporary Home is ready for you to finish, your way. Located on a dead-end road in the beautiful Hamlet of Shokan, Town of Olive, this Contemporary Home is set on +/- 1.7 acres of land offering a nice sense of privacy. The

    Edwin Maldonado Howard Hanna Rand Realty

    12 Fern Ln, Shokan, NY 12481
  • /28

    $299,000

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

    50 Harris Rd, Kerhonkson, NY 12446

    Turn-key renovated 3BR/2BA home at the end of a quiet cul-de-sac on a private road. Features hardwood floors throughout, a rustic-modern living area with pellet stove, and a bright updated kitchen with shaker cabinets, subway tile backsplash, and modern appliances. Both baths are refreshed and bedrooms are warm and move-in ready. Includes updated LG washer/dryer, multiple AC units, updated

    Ron Knowles Century 21 Alliance-NP

    50 Harris Rd, Kerhonkson, NY 12446
  • /21

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    76 Wynkoop Dr, Kerhonkson, NY 12446

    Nestled on just over one acre along a quiet, wooded private road, this inviting 3-bedroom, 2-full-bath ranch offers peaceful living in the heart of beautiful Ulster County. A covered front porch welcomes you into a warm and thoughtfully designed home featuring knotty pine wide-plank floors, solid wood doors, and wood trim and details throughout—creating a rustic yet modern feel. Neutral, clean

    Danielle Bartula Howard Hanna Rand Realty

    76 Wynkoop Dr, Kerhonkson, NY 12446
  • /36

    $549,900

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

    1441 County Road 2, Olivebridge, NY 12461

    Welcome to 1441 County Road 2 in Olivebridge, NY. This 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

    Nicholas Cuomo Keller Williams Realty

    1441 County Road 2, Olivebridge, NY 12461
  • /4

    $209,000

    • Land
    • 1.6 Acres
    • $130,625 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
  • /35

    $360,000

    • 1 Bed
    • 1 Bath
    • 405 Sq Ft

    26 Kelder Rd, Olivebridge, NY 12461

    Welcome to this exceptional modern A-frame retreat, newly built in 2023 and thoughtfully enhanced with quality upgrades throughout 2024. Nestled on 2.6 acres of natural beauty near the Ashokan Reservoir, this property blends expert craftsmanship, modern efficiency, and serene mountain living - minutes from Woodstock, Phoenicia, Shokan and Stone Ridge. Inside, you'll find Pella windows, sealed

    Nur Yilmaz Four Seasons Sotheby's Int'l-K

    26 Kelder Rd, Olivebridge, NY 12461
  • /22

    $450,000

    • 2 Beds
    • 1 Bath
    • 880 Sq Ft

    197 Trails End Rd, Kerhonkson, NY 12446

    Discover your own slice of mountain paradise where adventure literally begins at your doorstep. Set at the end of the rural, aptly named Trails End Road, this stunning modern cabin sits at the gateway to 19,000 acres of Sundown Forest, a wilderness with a system of hiking trails that starts just steps away. Completely renovated, rebuilt from the studs inside and out, this modern just-right

    Antonio Parrotta Coldwell Banker Village Green

    197 Trails End Rd, Kerhonkson, NY 12446
  • /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
  • /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
  • /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
  • /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

    Kristen Zigouras eXp Realty

    14 Saw Pitt Rd, Kerhonkson, NY 12446
  • /35

    $549,900

    • 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
  • /31

    $599,900

    • 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
  • /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 BHHS Nutshell Realty

    1626 County Road 2, Olivebridge, NY 12461
  • /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
  • /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
  • /15

    $499,000

    • Land
    • 10 Acres
    • $49,900 per Acre

    547 Glenford Wittenberg Rd, Bearsville, NY 12409

    This is an 86.2 acre property that is being subdivided into two- 3 acre parcels and one-10 acre parcel. The 10 ac parcel will be on the pond and the two 3 acre parcels are across the street from Yankeetown Pond. There are no houses for sale just land. There are beautiful views of the mountains and of Yankee Town Pond. The 10 acre parcel on the pond can have a structure build on it. There are 2+

    Siobhan Scanlan Win Morrison Realty-K

    547 Glenford Wittenberg Rd, Bearsville, NY 12409
  • /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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