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
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  /41

  $2,400,000

  • 4 Beds
  • 3 Baths
  • 2,751 Sq Ft

  53 Freeman Avery Rd, Olivebridge, NY 12461

  Modern Marvel in Nature!! Perched atop a private 40-acre wooded sanctuary, this architecturally significant prefabricated modular home—designed by award-winning Resolution: 4 Architecture—offers a rare combination of design-forward living and immersive natural surroundings. Built in 2012 and spanning over 3,671 square feet, this four-bedroom, three-bathroom residence is a true retreat in the

  

  Michael Carr

  eXp Realty

  (845) 684-9454

  53 Freeman Avery Rd, Olivebridge, NY 12461
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  /25

  $344,900

  • 2 Beds
  • 2 Baths
  • 848 Sq Ft

  442 Acorn Hill Rd, Olivebridge, NY 12461

  Charming & Updated 2-Bedroom Home in a Serene Country Setting. Discover this beautifully updated 2-bedroom, 2-bathroom home nestled in a private and peaceful location. With modernized electrical and mechanical systems, this home offers both comfort and reliability. The second-floor bathroom is brand new, adding a touch of luxury to the space. Step outside onto the lovely deck overlooking the

  

  Win Morrison

  Win Morrison Realty

  (845) 377-9502

  442 Acorn Hill Rd, 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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  /30

  $829,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  4 Burger Dr, Kerhonkson, NY 12446

  For those seeking a turnkey retreat with contemporary farmhouse charm, this newly built home on 1.3 acres is a true standout. Thoughtfully designed for both beauty and low maintenance, it features white Hardie board and batten siding, bluestone patios, cedar accents, and efficient Pella windows. A picturesque pond with tall cattails and a floating stone platform adds to the serene setting, while

  

  Catherine Quintard

  Compass Greater NY, LLC

  (845) 599-0447

  4 Burger Dr, Kerhonkson, NY 12446
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  /22

  $985,000

  • 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

  $825,000

  • 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 SUNDAY 8/24 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 and

  Richard Greenspan Ruth Gale Realty

  252 Upper Boiceville Rd, Boiceville, NY 12412
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  /61

  $899,000

  • 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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  /38

  $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
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  /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

  $989,000 New Construction

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

  805 County Road 2, Accord, NY 12404

  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 complete display of excellence. Arriving

  Zachary Jarvis Berkshire Hathaway Homeservice

  805 County Road 2, Accord, NY 12404
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  /42

  $2,399,000 Open Sun 11AM - 1PM

  • 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
  • 560 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

  $399,000

  • 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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  /20

  $189,900

  • Land
  • 2.60 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
  • 28 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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  /26

  $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 Hudson Dwellings Realty

  174 Palentown Rd, Kerhonkson, NY 12446
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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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  /17

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,647 Sq Ft

  121-1 Mountain Rd, Shokan, NY 12481

  RECENTLY REDUCED! THIS HOME IS A MUST SEE IN PERSON!Welcome to 121-1 Mountain Road in Shokan, NY! Nestled in this tranquil town, this charming ranch styled home offers a seamless blend of comfort, creativity, and outside natural beauty. Set back from the road on a 1.6 acre lot, this residence spans over 1600 sq. ft of connected living and dining space, with room to grow and

  Jayme Staten United Real Estate HV Edge

  121-1 Mountain Rd, 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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  /9

  $75,000

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

  281 Dewitt Rd, Olivebridge, NY 12461

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

  Hilton Purvis Coldwell Banker Village GreenN

  281 Dewitt Rd, Olivebridge, NY 12461
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  /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
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  /47

  $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
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  /7

  $110,000

  • Land
  • 2.60 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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  /24

  $349,000

  • 4 Beds
  • 2.5 Baths
  • 3,330 Sq Ft

  31 Lang Rd, West Shokan, NY 12494

  Bring your vision to this charming home in West Shokan, nestled amidst the Catskill Mountains. This spacious 4-bedroom, 2.5-bath home offers a generous 3,330 square feet of living space, situated on 1 acre of land. The charming 1 bed 1 bath accessory apartment holds significant potential for a guest/in-law suite or rental opportunity. This homes thoughtful floor plan seamlessly connects the

  Richard Vizzini Corcoran Country Living

  31 Lang Rd, West Shokan, NY 12494
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  /25

  $209,000

  • Land
  • 4.70 Acres
  • $44,468 per Acre

  00 Wynkoop Dr, Rochester, NY 12446

  Elevate your life in the heart of the Hudson Valley. Stop dreaming of weekend getaways and start living amidst the natural beauty. This tranquil property, perfect for your custom build, boasts direct access to local hiking trails and the picturesque Ashokan Reservoir for walking and biking. Encompassing three parcels sold together, this builder's dream offers unique potential, including existing

  Monica Noll Keller Williams Realty HV Nort

  00 Wynkoop Dr, Rochester, NY 12446
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  /27

  $209,000

  • 2 Beds
  • 1 Bath
  • 980 Sq Ft

  93 Wynkoop Dr, Kerhonkson, NY 12446

  Elevate your life in the heart of the Hudson Valley. Stop dreaming of weekend getaways and start living amidst the natural beauty. This tranquil property, perfect for your custom build, boasts direct access to local hiking trails and the picturesque Ashokan Reservoir for walking and biking. Encompassing three parcels sold together, this builder's dream offers unique potential, including existing

  Monica Noll Keller Williams Realty HV Nort

  93 Wynkoop Dr, Kerhonkson, NY 12446
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  /32

  $469,000

  • 3 Beds
  • 1.5 Baths
  • 1,466 Sq Ft

  5147 State Route 213, Olivebridge, NY 12461

  This great mixed-use property in the heart of Olivebridge, has a lot to offer, whether owner-occupied or strictly used as an income property. The first floor contains 1,850 SQ FT of commercial space leased to the US Postal Service, a Loading dock, and plenty of parking. An additional 75 SF indoor utility room. On the top floor, you will find a beautifully renovated, 1,150 sq. ft., 3-bedroom

  Louis Naccarato BERARDI REALTY

  5147 State Route 213, Olivebridge, NY 12461
• 

  

  /11

  $219,000

  • 2 Beds
  • 1 Bath
  • 1,077 Sq Ft

  3382 State Route 28, Shokan, NY 12481

  MOTIVATED SELLER!!! This charming cottage nestled in the scenic town of Olive was built in 1921.There is a lot of natural light highlighting the unique characteristics this house has to offer. This house features a generator hook up and on the property you will find a one-bedroom mobile home that is grandfathered in. It has its own septic and shared well with the house and it is a great rental

  Siobhan Scanlan Win Morrison Realty-K

  3382 State Route 28, Shokan, NY 12481

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