53 properties 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 acc

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 acc

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

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

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

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

There are homes that ask you to compromise, and then there are homes that ask you to dream. Set against a backdrop of sweeping mountain views, this is a rare opportunity to create something that's unmistakably yours. The hardest work has already been done. What's left is the part that reflects your style, your vision, and the way you want to live. Picture slow mornings with coffee overlooking the mountains, evenings spent watching the seasons change, and a home finished exactly the way you've always imagined-not someone else's choices, but your own. Whether your vision includes warm natural finishes, clean modern lines, or a timeless mountain retreat, this property is ready for the next chapter. In a market where finding the right location is nearly impossible, opportunities like this don't come along often. For generations, Bearsville and neighboring Woodstock have drawn musicians, painters, writers, makers, and free spirits seeking inspiration, community, and a different pace of life

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

On a private road and tucked away amidst towering pines sits 4 Tetta, a modern farmhouse that offers the kind of upstate escape that has become increasingly difficult to find: turnkey, secluded and surrounded by nine private acres with its own pond within easy access to various points of interest in the Rondout Valley. A bluestone entry leads to wide-plank pine floors and sun-filled living spaces, anchored by a substantial stone wood-burning fireplace. Inside, approximately 3,000 square feet unfold across multiple finished levels, with four bedrooms and four full baths providing plenty of space to gather, host, and retreat. The kitchen pairs custom cabinetry with a Bertazzoni range and built-in wine refrigerator, while thoughtfully finished bathrooms carry the same sense of craftsmanship throughout the home. Outside, nature beckons. Mornings begin on the screened porch where sunlight dapples the yard and forest. Afternoons drift between the woods, a private pond and a fire pit and an e

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

Welcome to this lovely 2-bedroom Mid-Century Modern home, with the classic clean lines and warmth that make you feel right at home. The spacious kitchen features a bay window looking out over the mountains and big sky, and the living room's picture window offers those same peaceful views. Original hardwood floors add a sense of solidity throughout, and two generously sized bedrooms with double closets create comfortable retreats. At the rear of the property you'll find a secluded wooded area filled with beautiful Spring ephemerals as well as numerous native flowering and fruiting plants; truly a delightful spot. The full basement is equipped with laundry facilities and a large, handy workbench. This home is equipped with a whole house generator for added peace of mind

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

A unique Catskills investment opportunity in the heart of Olivebridge, set privately on three picturesque acres along a bucolic country road. The property consists of three separate rental units: a duplex building with two generously sized apartments and a charming stand-alone cottage, offering flexibility for an investor, multi-generational living, or an owner looking to offset expenses with rental income. Adding to the property's appeal is an additional detached building, currently gutted and used for storage. Once believed to have been a garage and later converted into a hunting cabin/lodge, this structure was historically heated by a wood stove and offers intriguing possibilities for future restoration or creative reuse, subject to approvals. An attached two-car garage provides additional storage and utility space. Throughout the property, you'll find an abundance of beautiful stonework that adds character and a true sense of place to the grounds. Privately sited yet surrounded by

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

The Coldbrook Estate Discover unparalleled luxury and natural beauty with this exquisite new construction, perfectly sited on over 54 acres and bordered by thousands of acres of pristine State Land. This property offers an extraordinary living experience with direct waterfront access to the Esopus Creek, and seamless entry to the Ashokan Rail Trail. A rare combination of seclusion and outdoor access in the heart of the Catskills. This meticulously constructed 3-bedroom, 3.5-bathroom home showcases exceptional craftsmanship and attention to detail. The great room serves as the heart of the home, featuring a dramatic floor. To.ceiling stone fireplace as its centerpiece with soaring wood ceilings and exposed beams. French doors lead to a spacious 600 sq ft bluestone patio enclosed by a screened-in porch, ideal for entertaining or relaxing framing uninterrupted mountain and forest views. The chef's kitchen pairs custom cabinetry with a soapstone island, carrara marble counters and backspla

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

The Coldbrook Estate Discover unparalleled luxury and natural beauty with this exquisite new construction, perfectly sited on over 54 acres and bordered by thousands of acres of pristine State Land. This property offers an extraordinary living experience with direct waterfront access to the Esopus Creek, and seamless entry to the Ashokan Rail Trail. A rare combination of seclusion and outdoor access in the heart of the Catskills. This meticulously constructed 3-bedroom, 3.5-bathroom home showcases exceptional craftsmanship and attention to detail. The great room serves as the heart of the home, featuring a dramatic floor. To.ceiling stone fireplace as its centerpiece with soaring wood ceilings and exposed beams. French doors lead to a spacious 600 sq ft bluestone patio enclosed by a screened-in porch, ideal for entertaining or relaxing framing uninterrupted mountain and forest views. The chef's kitchen pairs custom cabinetry with a soapstone island, carrara marble counters and backspla

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

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

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