119 houses for sale in Shady, Woodstock town Ulster County New York

Wend up your forested driveway to this idyllic piece of paradise - 12 secluded acres, just minutes from Woodstock Village. The current owner/architect/builder designed this uniquely curated home and its surroundings to create the penultimate natural setting. As the house is revealed through the trees, a mirror image is reflected in the 13' deep, swimmable, mini-lake. BREATHE! That's the perfect response to this awe-inspiring locale. 6 springs feed this silky clear, 'Catskill clean' water feature; kept pristine by 2 aeration systems providing clear, oxygenated water for this bass-stocked body. There's a dock and fountain, and the water's edge is peppered with locally sourced boulders providing numerous places for diving, sun bathing, and meditating on the picturesque landscape. All this is just a few hand-picked, stone steps from a splendid 2 BR, 2 bath, Frank Lloyd Wright inspired, prairie-style home capped by an English style Tudor chimney featuring superlative brick accents. The curv

Wend up your forested driveway to this idyllic piece of paradise - 12 secluded acres, just minutes from Woodstock Village. The current owner/architect/builder designed this uniquely curated home and its surroundings to create the penultimate natural setting. As the house is revealed through the trees, a mirror image is reflected in the 13' deep, swimmable, mini-lake. BREATHE! That's the perfect response to this awe-inspiring locale. 6 springs feed this silky clear, 'Catskill clean' water feature; kept pristine by 2 aeration systems providing clear, oxygenated water for this bass-stocked body. There's a dock and fountain, and the water's edge is peppered with locally sourced boulders providing numerous places for diving, sun bathing, and meditating on the picturesque landscape. All this is just a few hand-picked, stone steps from a splendid 2 BR, 2 bath, Frank Lloyd Wright inspired, prairie-style home capped by an English style Tudor chimney featuring superlative brick accents. The curv

The essence of Woodstock; the artists, the poets, the musicians and the creatives who have gravitated to the beautiful, iconic Catskill Mountain town, no-one embodies the original spirit of Woodstock more than local artist and environmentalist Calvin Grimm. Every home tells a story. This custom built home. Tucked away on 2 private acres with mountain views on a dead end lane speaks volumes. 1 bedroom/ 2 bathroom home with climate controlled, art studio. This labor of love Calvin created over 5 decades, reflects his artistry, his ingenuity and simply his dear love for this place. Calvin's maternal grandparents would summer in Woodstock and eventually Calvin would as well, beginning when Calvin was just a few weeks old. In the 1960's before the infamous concert put Woodstock on the global map, Calvin was in his early twenties with just enough to purchase his own parcel of land. When he came upon this special spot full of rock outcroppings, mountain laurel and maple tucked on the side of

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

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 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

Relax, unwind, and take in the views from this charming cottage on one of the most bucolic and peaceful roads in the Woodstock hamlet of Willow-where every day feels like a weekend escape. The tranquility, mountain views, and picturesque valley setting have been cherished by one family for 47 years. Tucked away from the road and nearly invisible to passersby, the property welcomes you with the soothing sounds of water cascading down the hillside away from the house for much of the year. The owners have preserved a natural garden alongside the house, filled with ferns, daylilies, daffodils and native greenery that support the surrounding ecosystem. A deck provides a wonderful introduction to the home and offers the perfect setting for morning coffee, family barbecues, or simply relaxing outdoors. In the evening, enjoy stargazing while listening to the peaceful sounds of nature. The spacious screened porch is accessible from both the deck and the interior of the home. An overhead fan enh

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

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

Charming, turnkey remodeled 1840s farmhouse with mountain views on a quiet country road, offering the perfect blend of historic character and modern comfort. This 4-bedroom, 2-bath home features wide-plank wood floors upstairs, an eat-in kitchen with mountain views, a pass-through pantry leading to the formal dining room, and a spacious living room with adjoining flex space and a separate entrance—ideal for a home office, studio, guest suite, or additional living area. Upstairs you'll find 4 bedrooms and a full bath, with light streaming through the windows and mountain views in back of the house. Enjoy the welcoming rocking chair front porch, relax in the hot tub, and take advantage of the storage shed and peaceful setting. With a proven history as a successful short-term rental (Airbnb), this income-producing property offers exceptional flexibility as a primary residence, second home, or investment opportunity. It can also be purchased with all the furnishings to make this 100% turnk

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

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

Directly across from Cooper Lake and tucked quietly among the trees just minutes from Woodstock, this rare Catskills compound captures the kind of escape buyers dream about but rarely find. Surrounded by woods, mountain air, hiking, legendary fly-fishing waters, and the natural beauty that defines the Catskills, the property offers a unique blend of privacy, flexibility, creative space, and income potential. Set on 1.645 surveyed acres with multi-family residential zoning, the property includes a beautifully updated main residence, a separately positioned renovated cottage, and a substantial detached garage/studio building. Ideal for full-time living, weekend retreat use, guest accommodations, artist studio space, work-from-home flexibility, or rental income. Warm and inviting living spaces connect naturally to the outdoors, including a covered deck designed for year-round enjoyment beneath the trees. The detached cottage has been extensively renovated and includes its own electric ser

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

Cooper lake! Woodstock! Need I say more. Major price reduction. Ripe for renovation. The front porch needs demolition. The main roof ridge is nice and straight. Don't miss this opportunity to create an idyllic country escape in one of Woodstock's most sought-after areas. Direct views of Cooper Lake are seen from the property. It could be enhanced with minimal clearing. A porion of the 2.3 Acre property is in a designated Wetland. Abundant wildlife can be seen around the lake. The home has been lived in up until last month, but needs a complete overhaul, at the very least. Bring your Contractor and Architect The 440 Sq. Ft. Accessory Outbuilding would make an excellent Studio / Guest House and has100 Amp Electric Service Take advantage of this opportunity to create a magical Country Escape. Just 5 Miles fron the center of Woodstock and all it has to offer. Easy to show. Use Showing Time to schedule

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

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

The essence of Woodstock; the artists, the poets, the musicians and the creatives who have gravitated to the beautiful, iconic Catskill Mountain town, no-one embodies the original spirit of Woodstock more than local artist and environmentalist Calvin Grimm. Every home tells a story. This custom built home.tucked away on 2 private acres with mountain views on a dead end lane speaks volumes. 1 bedroom/ 2 bathroom home with climate controlled, art studio. This labor of love Calvin created over 5 decades, reflects his artistry, his ingenuity and simply his dear love for this place. Calvin's maternal grandparents would summer in Woodstock and eventually Calvin would as well, beginning when Calvin was just a few weeks old. In the 1960's before the infamous concert put Woodstock on the global map, Calvin was in his early twenties with just enough to purchase his own parcel of land. When he came upon this special spot full of rock outcroppings, mountain laurel and maple tucked on the side of t

The essence of Woodstock; the artists, the poets, the musicians and the creatives who have gravitated to the beautiful, iconic Catskill Mountain town, no-one embodies the original spirit of Woodstock more than local artist and environmentalist Calvin Grimm. Every home tells a story. This custom built home.tucked away on 2 private acres with mountain views on a dead end lane speaks volumes. 1 bedroom/ 2 bathroom home with climate controlled, art studio. This labor of love Calvin created over 5 decades, reflects his artistry, his ingenuity and simply his dear love for this place. Calvin's maternal grandparents would summer in Woodstock and eventually Calvin would as well, beginning when Calvin was just a few weeks old. In the 1960's before the infamous concert put Woodstock on the global map, Calvin was in his early twenties with just enough to purchase his own parcel of land. When he came upon this special spot full of rock outcroppings, mountain laurel and maple tucked on the side of t

Rare investment opportunity in Woodstock: a collection of five unique cottages on six wooded acres located just minutes from the Village's vibrant shops, dining, and nightlife. Each home boasts a distinct personality and peaceful forest views, and all five have been successfully rented with a combination of short- and long-term tenants. Possibilities include renting all five cottages or living in one while renting the other four. Another option is to create a warm and inviting 5-cottage compound for group living. Imagine enjoying the Woodstock lifestyle with loved ones just a door-knock away. For a writer, artist, or home-business owner, perhaps one or more of the cottages could be used as a studio or office separate from home. Cottage 1 is a delightful two bedroom/one bath with a fireplace and Craftsman kitchen. Cottage 2, with one bed and one bath, was reimagined and fully renovated in 2024. Cottage 3 is peak contemporary treehouse: a stunning two bedroom/two bath, featuring dramatic

Rare investment opportunity in Woodstock: a collection of five unique cottages on six wooded acres located just minutes from the Village's vibrant shops, dining, and nightlife. Each home boasts a distinct personality and peaceful forest views, and all five have been successfully rented with a combination of short- and long-term tenants. Possibilities include renting all five cottages or living in one while renting the other four. Another option is to create a warm and inviting 5-cottage compound for group living. Imagine enjoying the Woodstock lifestyle with loved ones just a door-knock away. For a writer, artist, or home-business owner, perhaps one or more of the cottages could be used as a studio or office separate from home. Cottage 1 is a delightful two bedroom/one bath with a fireplace and Craftsman kitchen. Cottage 2, with one bed and one bath, was reimagined and fully renovated in 2024. Cottage 3 is peak contemporary treehouse: a stunning two bedroom/two bath, featuring dramatic

Set on more than nine private acres just minutes from the heart of Woodstock, this elegant sprawling ranch is a rare offering where the views take center stage. Thoughtfully designed in the spirit of 1960s contemporary architecture, the home was created to celebrate its extraordinary natural setting, with sweeping vistas enjoyed from nearly every room. A substantial spring-fed pond, serene pine forest, and dramatic 180-degree Catskill Mountains views create a setting that is both tranquil and unforgettable. The open floor plan enhances the home's effortless flow and inviting, inclusive style of living. A dramatic screened porch with cathedral ceilings, along with an expansive wood deck, offers exceptional spaces for outdoor dining, entertaining, or simply taking in the surrounding beauty. Inside, a bluestone fireplace anchors the living room, while a curved glass wall, dining area, eat-in kitchen with skylight, and breakfast bar all contribute to the home's warmth, comfort, and easy li

Prime Income Property Vacant Woodstock 2-Family Opportunity Delivered Vacant-maximize your portfolio's ROI from day one. Savvy investors and owner-occupants, take note: this exceptionally located 2-family property offers immediate cash-flow potential with zero tenant transition hassle. Set your own market-rate rents right away in the high-demand Woodstock Hamlet rental market. The Units: The property consists of two highly rentable 500 sq. ft. studio units, each with an open layout. Inside, you'll find a low-maintenance, tenant-proof blend of warm hardwood and durable ceramic tile flooring. A major tenant draw is the private, south-facing sun porch included with each unit. Investor Advantages From a management perspective, this asset is designed for low overhead and ease of ownership: Infrastructure: Each apartment has separately metered electric. Municipal water and sewer obviate repair and upkeep concerns. Dedicated off street parking. Flexibility: Whether you are looking for a pure