99 houses for sale in Ashokan

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

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

The Dug Hill Rd House A family legacy, offered for the first time. Some homes come to market. This one comes to light for the very first. Built in 1969 by the current owner's father, this home has been loved, cared for, and privately passed down through one family. Now it's ready for a new story to begin. Tucked into 13.9 private acres and bordered by over 300 acres of protected state land on two sides, the setting is secluded yet the location remains surprisingly convenient to Kingston, Woodstock, Stone Ridge and so much more while only being 90 Min from the GWB, giving buyers the best of both worlds: privacy without sacrifice. The home offers 5 bedrooms, a dining room, and a large kitchen at its heart, along with 2 updated full bathrooms, an airy living room with vaulted ceilings and recessed lighting, plus an extra room perfect for an office, library, or media room. Below the home is an extra-large drive-under garage with ample space for vehicles, hobbies, and storage. Throughout th

There's a distinctly Bohemian heartbeat to this Woodstock compound - the kind of place where every corner feels like it has a story to tell or awaits the hearing of yours. The 1850 respectfully updated, original farmhouse, with its rich hand-hewn beams, gleaming wide floorboards, and six over six windows carries the patina of time, offering warmth, charm, and the kind of character that make old homes irresistible. The early 1990's addition expands the residence to provide alluring and flexible usage. This home is soulful, and available for those who appreciate authenticity. In the living room, with its two directions of light, an old brick fireplace anchors the space with rustic charm. The intimate, fully equipped kitchen with a natural stone seating bar and the beamed dining room feel like the heart of a true country home: Fetch, prepare and enjoy the local farmland bounty. The vaulted gathering room is dramatic with its absolutely fabulous wallpaper and 16' north light wall offering

The Dug Hill Rd House A family legacy, offered for the first time. Some homes come to market. This one comes to light for the very first. Built in 1969 by the current owner's father, this home has been loved, cared for, and privately passed down through one family. Now it's ready for a new story to begin. Tucked into 13.9 private acres and bordered by over 300 acres of protected state land on two sides, the setting is secluded yet the location remains surprisingly convenient to Kingston, Woodstock, Stone Ridge and so much more while only being 90 Min from the GWB, giving buyers the best of both worlds: privacy without sacrifice. The home offers 5 bedrooms, a dining room, and a large kitchen at its heart, along with 2 updated full bathrooms, an airy living room with vaulted ceilings and recessed lighting, plus an extra room perfect for an office, library, or media room. Below the home is an extra-large drive-under garage with ample space for vehicles, hobbies, and storage. Throughout th

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

There's a distinctly Bohemian heartbeat to this Woodstock compound - the kind of place where every corner feels like it has a story to tell or awaits the hearing of yours. The 1850 respectfully updated, original farmhouse, with its rich hand-hewn beams, gleaming wide floorboards, and six over six windows carries the patina of time, offering warmth, charm, and the kind of character that make old homes irresistible. The early 1990's addition expands the residence to provide alluring and flexible usage. This home is soulful, and available for those who appreciate authenticity. In the living room, with its two directions of light, an old brick fireplace anchors the space with rustic charm. The intimate, fully equipped kitchen with a natural stone seating bar and the beamed dining room feel like the heart of a true country home: Fetch, prepare and enjoy the local farmland bounty. The vaulted gathering room is dramatic with its absolutely fabulous wallpaper and 16' north light wall offering

There’s a distinctly Bohemian heartbeat to this Woodstock compound — the kind of place where every corner feels like it has a story to tell or awaits the hearing of yours. The 1850 respectfully updated, original farmhouse, with its rich hand-hewn beams, gleaming wide floorboards, and six over six windows carries the patina of time, offering warmth, charm, and the kind of character that make old homes irresistible. The early 1990’s addition expands the residence to provide alluring and flexible usage. This home is soulful, and available for those who appreciate authenticity. In the living room, with its two directions of light, an old brick fireplace anchors the space with rustic charm. The intimate, fully equipped kitchen with a natural stone seating bar & the beamed dining room feel like the heart of a true country home: Fetch, prepare and enjoy the local farmland bounty. The vaulted gathering room is dramatic with its absolutely fabulous wallpaper and 16’ north light wall offering pa

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

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

Tucked at the end of a private road just minutes from Woodstock, this exceptional five-bedroom, five-bath residence offers an uncommon combination of privacy, generous scale, and scenic charm. Set on approximately three acres and bordered by a year-round stream, the 3,722 square foot home feels wonderfully secluded while remaining close to the restaurants, shops, galleries, and creative energy of Woodstock. Originally built in 1952, the home has been carefully expanded, renovated, and extensively upgraded over the years. Recent improvements include a newly added en-suite bathroom for the primary bedroom, along with numerous updates throughout. The result is a sophisticated yet comfortable home designed for year-round living. Furnishings and decor are also available for purchase, making the transition remarkably seamless. Inside, generous windows and an open layout bring in the surrounding landscape. The high-end kitchen flows into the dining and living areas, creating an easy setting f

Hidden among the trees and just seven minutes from the center of Woodstock, this 1970s contemporary feels like a private creative compound, untouched in all the right ways. Set on 2 wooded acres with the Sawkill Creek at the rear of the property, the home unfolds through a series of unexpected spaces and strong architectural moments. A dramatic sunken living room anchors the house, centered around an oversized stone fireplace and framed by walls of glass that draw the surrounding landscape indoors. The original design language remains beautifully intact throughout, offering the rare opportunity to own a true period home rather than a generic renovation. The layout is expansive and flexible with over 2,700 square feet, 3 bedrooms, 2.5 baths, and multiple gathering spaces that open naturally toward the outdoors. Off the kitchen, a tucked-away courtyard deck creates an especially inviting area for dining, entertaining, or slow summer evenings beneath the trees. A luminous 500 sq ft porch

Welcome to 274 Morgan Hill Road, ideally situated on a desirable road in Hurley and offering a comfortable blend of space, functionality, and privacy. This well maintained 3-bedroom, 2-bath split-level home offers approximately 1,633 square feet of living space, with a layout designed for both everyday living and ease of entertaining. The interior provides a warm and inviting feel with well proportioned rooms and a natural flow throughout. The upper level features 2 bedrooms and 1 full bathroom, while the lower level offers a private primary bedroom suite with an additional full bathroom, creating a flexible layout suited to a variety of living arrangements. The backyard includes a detached screened sunroom area, providing a comfortable space to enjoy the outdoors in a more private setting. Set within a quiet neighborhood and a convenient Hudson Valley location, the property offers access to nearby amenities, commuter routes, and surrounding towns while maintaining a sense of space and

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

764 Lapla Road is the rare renovation where the craftsmanship is immediately apparent, but the experience of living here is what stays with you. Nearly 3,000 square feet unfold beneath warm pine beams milled from the property, with walls of black-framed Marvin windows bringing the gardens into virtually every room. Stone, wood, marble, brass and softly textured tile give the interiors a sense of permanence, while the open, light-filled plan feels remarkably easy and inviting. At the center of the house, the living room is anchored by an extraordinary stone fireplace, creating a natural gathering place that feels equally right on a winter evening or with the doors open to the gardens in summer. From here, the house flows into a generous dining area and a kitchen designed for people who genuinely enjoy cooking and entertaining. Custom inset cabinetry, unlacquered brass hardware, a cherry butcher-block island, apron-front sink, integrated Fisher & Paykel refrigeration and an AGA Mercury i

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

The Dug Hill Rd House A family legacy, offered for the first time. Some homes come to market. This one comes to light for the very first. Built in 1969 by the current owner's father, this home has been loved, cared for, and privately passed down through one family. Now it's ready for a new story to begin. Tucked into 13.9 private acres and bordered by over 300 acres of protected state land on two sides, the setting is secluded yet the location remains surprisingly convenient to Kingston, Woodstock, Stone Ridge and so much more while only being 90 Min from the GWB, giving buyers the best of both worlds: privacy without sacrifice. The home offers 5 bedrooms, a dining room, and a large kitchen at its heart, along with 2 updated full bathrooms, an airy living room with vaulted ceilings and recessed lighting, plus an extra room perfect for an office, library, or media room. Below the home is an extra-large drive-under garage with ample space for vehicles, hobbies, and storage. Throughout th

Tucked away on approximately 2.54 acres in Stone Ridge, Stillwater is a bright, character-rich 1980 Green Mountain Homes passive-solar house with an unusual concentration of systems already in place: owned grid-tied solar with working battery backup that can power designated household loads during outages, multiple heating and cooling options, private well and septic, protected growing space, mature gardens, a woodstove, and a powered two-story garage/barn. The result is a house that feels like both a beautiful, design-forward country home and a deeply capable, climate-conscious property. Comfortable, redundant, and ready for the future we're already living in. The house was designed from the beginning to work with its site, using passive solar, thermal mass, an original Solar Slab and circulation system to capture, hold and move warmth through the home. Today that remarkably forward-thinking design is layered with owned, net-metered solar with working battery backup, a three-zone Fuji

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

Tucked into more than 6.5 tranquil acres in low-tax Hurley, this cedar-sided Cape offers warmth, privacy, and a connection to its natural surroundings. Inside you will find well proportioned spaces, flowing from an ample dining room and open kitchen to a cozy living room warmed by a woodstove. The beautiful custom kitchen features solid wood cabinetry, Wolf and Subzero appliances, and striking quartzite countertops. Original Douglas fir floors extend throughout both levels, while radiant heat and central air conditioning provide year-round comfort. Up the custom walnut-and-maple staircase, four generously sized bedrooms await. A second-floor sun deck is accessible from two of the bedrooms, offering a peaceful place to enjoy the treetop setting. Outside, the property feels almost magical-quiet, private, and filled with the sounds of nature. Fall asleep listening to the owls and wake to the songbirds. An old quarry that holds water offers intriguing potential; the current owner envisione

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

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

Welcome to easy, one-level living in Woodstock! This inviting ranch offers the perfect blend of comfort, convenience, and charm-ideal for first-time buyers, weekenders, downsizers, or investors seeking a move-in ready home close to all the action. Step inside to a bright, open-concept layout, where the kitchen, dining, and living areas flow seamlessly together-perfect for everyday living and entertaining. The large front mid-century windows flood the space with natural light, creating a warm and welcoming atmosphere. You'll love the oversized bathroom, thoughtfully designed with double sinks, two generous windows, and tile flooring to make busy mornings a breeze. Year-round comfort is yours with three brand new split units, offering energy-efficient heating and cooling. The freshly painted interior provides a crisp, modern feel, while new stainless appliances and a stacked washer/dryer add everyday convenience. Outside, enjoy a spacious, fenced-in backyard-ideal for pets, gardening, or

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

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