44 houses for sale in West Shokan

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. Beyond that is NYC property. Inside, the home showcases its heritage with stunning original chestnut beams-many of which remain structural and weight-bearing-bringing warmth, authenticity, and architectural significance to the living space. A striking chimney, masterfully crafted both inside and out by a local mason, serves as a centerpiece, anchoring the home with timeless craftsmanship. The setting is equally compelling. A pristine, swimmable spring-fed pond invites peaceful afternoons and reflects the surrounding mountain landscape, creating a private retreat-like atmosphere. The property is ac

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. Beyond that is NYC property. Inside, the home showcases its heritage with stunning original chestnut beams-many of which remain structural and weight-bearing-bringing warmth, authenticity, and architectural significance to the living space. A striking chimney, masterfully crafted both inside and out by a local mason, serves as a centerpiece, anchoring the home with timeless craftsmanship. The setting is equally compelling. A pristine, swimmable spring-fed pond invites peaceful afternoons and reflects the surrounding mountain landscape, creating a private retreat-like atmosphere. The property is ac

203 Watson Hollow Road is a Creekside Gem Close to Woodstock, NY. A beautiful and impeccably maintained single-family home tucked away on a quiet road near the Ashokan Reservoir includes three bedrooms and one bathroom. The property is a tranquil paradise for outdoor enthusiasts. The gorgeous creek flows year-round and is surrounded by lovely trees and foliage. This exceptional cottage residence is warm and inviting with two wood-burning fireplaces. A stone, wood-burning fireplace is in the living room and another wood burning fireplace in the primary bedroom. A delightful sunroom is ready for entertaining, or reading your favorite book. The kitchen has all the appliances you will need for home cooking. A dishwasher can be added, if desired. There is a washer and dryer, the heating source is propane and central air conditioning was added in 2026, The roof is also new. Effortless convenience to Woodstock, Kingston, and the NY State Thruway makes this dream home in the Hudson Valley the

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. Beyond that is NYC property. Inside, the home showcases its heritage with stunning original chestnut beams-many of which remain structural and weight-bearing-bringing warmth, authenticity, and architectural significance to the living space. A striking chimney, masterfully crafted both inside and out by a local mason, serves as a centerpiece, anchoring the home with timeless craftsmanship. The setting is equally compelling. A pristine, swimmable spring-fed pond invites peaceful afternoons and reflects the surrounding mountain landscape, creating a private retreat-like atmosphere. The property is ac

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Nestled among the trees and tucked back from the road, this immaculate Olivebridge retreat offers the kind of peace and privacy people move upstate for. Quiet, serene, and thoughtfully updated throughout, the property feels effortlessly welcoming from the moment you arrive. Inside, the home feels bright, comfortable, and incredibly well cared for. Sun pours through the windows, the wood stove adds a cozy touch in colder months, and the entire space has an easy, relaxed flow. Recent upgrades include a whole house generator, new driveway, and numerous improvements throughout, making the home feel completely move in ready. A small private deck off the primary bedroom overlooks the beautiful backyard, the perfect spot for slow mornings, evening wine, or listening to the trees move in the breeze. The expansive yard offers endless potential for a pool, gardens, or outdoor entertaining while still feeling incredibly private. One of the standout features of the property is the impressive 1,600

The Pines | Mt Tremper, New York A rare chance to steward one of the Catskills' most storied properties has quietly arrived. The Pines. A cherished roadside inn and restaurant nestled between Woodstock and Phoenicia. Is ready for its next chapter. With more than five decades as a beloved Italian restaurant followed by a decade-long reinvention as a community gathering place, The Pines carries the kind of lived-in warmth that simply cannot be manufactured. What's on offer here isn't just a property. It's a place people return to. Set on 3.36 acres, the grounds balance openness and intimacy: rolling fields, pockets of woodland, and direct waterfront access to the Beaverkill Creek. The main building operates as a functioning roadside lodge, with five upstairs suites. Two with en suite baths and three sharing a beautifully appointed common bath. Alongside a full kitchen, dining area, and a living room that invites lingering. A covered porch extends the experience outdoors, offering guests

Casa Jane Some homes are simply lived in. Others are cultivated over time. Shaped quietly through care, intention, and a deep connection to the land. Casa Jane belongs to the latter. Set on four private acres in the heart of the Catskills, Casa Jane offers a rare combination of mountain views, creek frontage, fully fenced grounds, a Gunite pool, and over two decades of professionally designed landscaping that has transformed the property into a private botanical sanctuary. Just minutes from Woodstock's vibrant restaurants, galleries, and creative energy. Yet feeling entirely removed from it. This is a home that balances privacy, nature, and thoughtful living in a way that is increasingly difficult to find. The nearly 3000 square foot home unfolds across three thoughtfully designed levels, each offering its own rhythm and purpose. The main level is centered around an expansive open kitchen, dining, and living space designed for gathering and connection. Warm and welcoming in feel, the k

Updated Storybook Farmhouse with Mountain Views and Stream Set in the heart of Mount Tremper with mountain views and a classic farmhouse feel, this thoughtfully updated early 1900s home blends original character with carefully considered modern improvements. Warm, welcoming, and full of charm, the property feels deeply connected to its Catskills setting, with details that speak to its history while offering the comfort and functionality that make everyday living easy. A welcoming entry with classic ceramic tile opens into the home's light-filled interior, where original details and historic character can be felt throughout. The spacious living room is anchored by a handcrafted bluestone wood-burning fireplace that invites cozy winter evenings by the fire, while the bay window offers the perfect place to curl up with a book or morning coffee and take in the landscape. The newly renovated kitchen feels elevated yet true to the character of the home. Thoughtfully designed and beautifully

Tucked into a dramatic rock ridge with sweeping views of the Catskill Mountains, this renovated farmhouse invites you to slow down and savor country living at its finest. Spanning just over 3,000 square feet, the home balances rustic character with thoughtful modern updates throughout. The renovated kitchen, anchored by warm butcher block counters, flows gracefully into a generous dining room. From there, step into the cozy living room, where windows on every side pull the outdoors in. It's the kind of layout that makes both quiet mornings and lively gatherings feel effortless. Upstairs, the primary suite steals the show with spectacular mountain vistas, a walk-in closet, and a beautifully renovated bathroom featuring a soaking tub perfectly positioned to enjoy the view. An additional bedroom and full bath share this level, along with a spacious flex room and sleeping loft ready to serve as a home office, gym, or guest quarters. The finished third-floor attic opens up even more possibi

Set well back from the road behind a handsome gated entry, this modern Catskills hideaway delivers the privacy everyone wants and the volume everyone hopes for. The approach is long and quiet; the house reveals itself slowly-wrapped by trees, with sky above and room to breathe on 4.04 acres. Inside, an airy great room rises with high ceilings and broad windows that pull in daylight and treetops. A wood-burning fireplace anchors the space and gives the room an easy, year-round center of gravity. The plan flows to dining and out to the covered front porch for rainy-day coffee and a sunny deck for afternoons-simple, usable spaces that invite you to linger. 3 bedrooms, 2 full baths, office used as an extra bedroom, across about 2,772 sq ft, giving you comfortable proportions without wasted space. Downstairs, a full basement with a finished recreation room offers the flexible square footage every Catskills buyer asks for-think gym, studio, media, or gear room. Practical details are dialed:

Affordable Two-Family Opportunity in Shokan! Set on 2 acres with frontage along Route 28, this two-family home is ready for its next chapter. The first-floor unit features 2 bedrooms and 1 bath; the second-floor apartment includes 1 bedroom and 1 bath—ideal for extended family, rental income, or offsetting your mortgage. The property needs renovation, but the potential is real for first-time buyers, handy homeowners, or investors alike. Conveniently located near Woodstock, Phoenicia, and the Ashokan Reservoir, with easy access to hiking, skiing, shops, and dining. Check with the Town of Olive about possible business use

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 amazing newly painted Gambrel Roof Horse Barn, you can move them right in and start enjoying every aspect of country life. The peaceful feeling this private property gives is unmatched. The home is nestled perfectly along the woodlands with great views of the open fields. Watch your horses, cows or goats grazing or just relax on the open front porch and breath in all the fresh air! The home has been very well maintained and features a charming stone fireplace, pretty solid wood six panel doors, a kitchen with multiple wood cabinets including an integrated pantry, Corian countertops, a gas stove and pen

Low-Tax Olive Haven Set on 6.5 picturesque, quiet acres with the Shawangunk Ridge rising to the east, this beautifully renovated 18th century farmhouse feels like the place you've been looking for. Wide board floors, post and beam construction. The chef's kitchen includes a center island for prep and conversation, a dining table ready for long Sunday breakfasts, game night, or entertaining guests. The heart of the home is the great room, where picture windows flood the space with light and a woodstove waits for the first cold snap. On the third floor, a light-filled loft becomes whatever you need: a yoga studio, a home gym, or the writing retreat you've always wanted. With amazing views that make it hard to leave. The updates are already done for you: a new roof in 2018 with 50-year shingles, a new septic system in 2015, and mini-splits that handle heating and cooling year-round. Living in Olivebridge means having the best of the Hudson Valley right outside your door. Everyday errands

Motivated Seller*. Tucked away on a quiet dead-end road, this charming 3-bedroom, 2-bath ranch offers peaceful living on over 3 private acres. Built in 2005, the home features convenient one-level living with a well-designed layout, including central living spaces, a spacious primary suite with walk-in closet and private bath, and two additional bedrooms with a full guest bath. The kitchen provides ample cabinet space, dishwasher, and a convenient washer/dryer closet with access to the back deck. Enjoy the tranquil setting surrounded by nature, where wildlife sightings are a regular part of the landscape. The walk-out unfinished basement offers excellent potential for additional living space such as a media room, home office, or gym, and includes access to the one-car drive-under garage. Ideally located in the heart of the Catskills, this home offers the perfect balance of privacy and convenience. Enjoy being just 6 miles from the Ashokan Reservoir and only minutes from scenic hiking t

This charming cottage in Olivebridge NY proves that great things really do come in small packages. Thoughtfully designed for easy living, it's the kind of home that lets you spend less time maintaining and more time enjoying everything the Hudson Valley has to offer. Inside, warm and inviting spaces feel instantly welcoming, while an airy loft provides the perfect spot for a home office, creative studio, or cozy reading nook. Whether you're working remotely or simply looking for a quiet place to unwind, this home offers just the right amount of space and versatility. Outside, the beautifully established gardens create a private retreat that bursts with seasonal color, offering plenty of room to relax, entertain, or indulge your green thumb. Set on an easy-to-manage 1.3-acre lot with low property taxes, this is a home that's as practical as it is charming. Whether you're searching for a full-time residence, a weekend escape, or a low-maintenance country retreat, this magical home offers

This charming Olivebridge 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, and Tetta's Market, this inviting retreat has had a number of thoughtful upgrades. Come experience the best of upstate living in a prime location

There is something instantly comforting about this home. Warm, welcoming, and lovingly maintained, it offers the kind of easy living that never goes out of style. Whether gathering around the fireplace with friends, enjoying a quiet morning coffee, or unwinding after a long day, every space feels inviting, functional, and meant to be lived in. Set amidst peaceful natural surroundings with views across an open meadow, the property offers a sense of calm. A welcoming front porch invites you to slow down and savor the changing seasons, while the charming gazebo creates the perfect setting for outdoor dining, afternoon reading, or evenings spent enjoying the fresh country air. Offering approximately 1,900 square feet of living space, the interiors balance warmth with practicality. Engineered cherry floors flow throughout the main level, where radiant heat beneath your feet and a wood burning fireplace with electric fan create comfort in every season. Large Andersen double-pane windows fram

Set well back from the road behind a handsome gated entry, this modern Catskills hideaway delivers the privacy everyone wants and the volume everyone hopes for. The approach is long and quiet; the house reveals itself slowly-wrapped by trees, with sky above and room to breathe on 4.04 acres. Inside, an airy great room rises with high ceilings and broad windows that pull in daylight and treetops. A wood-burning fireplace anchors the space and gives the room an easy, year-round center of gravity. The plan flows to dining and out to the covered front porch for rainy-day coffee and a sunny deck for afternoons-simple, usable spaces that invite you to linger. 3 bedrooms, 2 full baths, office used as an extra bedroom, across about 2,772 sq ft, giving you comfortable proportions without wasted space. Downstairs, a full basement with a finished recreation room offers the flexible square footage every Catskills buyer asks for-think gym, studio, media, or gear room. Practical details are dialed:

Tucked into a dramatic rock ridge with sweeping views of the Catskill Mountains, this renovated farmhouse invites you to slow down and savor country living at its finest. Spanning just over 3,000 square feet, the home balances rustic character with thoughtful modern updates throughout. The renovated kitchen, anchored by warm butcher block counters, flows gracefully into a generous dining room. From there, step into the cozy living room, where windows on every side pull the outdoors in. It's the kind of layout that makes both quiet mornings and lively gatherings feel effortless. Upstairs, the primary suite steals the show with spectacular mountain vistas, a walk-in closet, and a beautifully renovated bathroom featuring a soaking tub perfectly positioned to enjoy the view. An additional bedroom and full bath share this level, along with a spacious flex room and sleeping loft ready to serve as a home office, gym, or guest quarters. The finished third-floor attic opens up even more possibi

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Tucked down a long driveway on 4.3 private, wooded acres, just outside Woodstock, this thoughtfully designed contemporary home offers the rare combination of true seclusion and effortless livability. Built with a post and beam, passive solar design, the home was constructed to work with its surroundings. Inside, 1,852 square feet are laid out across two comfortable levels, with 3 bedrooms and 2.5 baths. Both full baths were newly renovated this year. Heated floors run throughout both levels, keeping the home warm and quiet through every Catskills winter, while a cozy fireplace anchors the main living space. The eat-in chef's kitchen is a standout: a commercial Thermador range and hood, a wall-size Thermador refrigerator, a Thermador dishwasher and trash compactor make it as functional for everyday life as it is for entertaining. Every bathroom is outfitted with a TOTO heated bidet toilet and heated floors. The basement adds flexible living space, recreation space or storage. Fresh pain

11 Blue Heron Drive, Marbletown Fabulous 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 property) and is surrounded by mature trees, abundant birdlife, and the soothing sounds of nature. A gracious, tree-lined driveway creates a beautiful approach to this meticulously maintained home. The property features a detached garage/workshop with a charming studio above, complete with a wood-burning stove-ideal for guests, creative space, or home office use. Fenced garden areas, open lawns, and peaceful views enhance the sense of privacy and tranquility. Perfectly located for outdoor enthusiasts, with easy access to scenic walking and biking along the Ashokan Reservoir, as well as nearby Catski