Courtesy: Compass Greater NY, LLC
845-677-5311
Situated at the end of a private road on three serene acres, 53 Blueberry Hill offers the opportunity to own a secluded sanctuary just three miles from Woodstock’s village center. Recently remodeled, this three-bedroom home, complete with a one-bedroom, one-bathroom detached studio, is an idyllic Catskills residence with ample space for everyone. Constructed from timbers logged on Blueberry Hill, the interior of the home features an open floor plan with a newly remodeled eat-in kitchen, a dining area sized for large groups, and an ample living room with a wood-burning stove. A newly renovated bathroom on the first floor features a tub/shower combination as well as a washer/dryer. The first floor also boasts generous outdoor space, with an oversized (and partially screened) deck spanning from the kitchen to the living room. Upstairs, there are three bedrooms, all with sleek built-in storage and skylights. The largest of the three bedrooms can accommodate a king bed and has both a walk-in closet and a sweet private balcony overlooking the forest and stone walls. The second floor features another renovated bathroom with a soaking tub and a wall of built-in closets connecting the two ends of the second story. Just moments from the front door of the main house is the studio, complete with a kitchenette and full bathroom. Currently in use as additional sleeping quarters, this space could also function beautifully as an art studio, home office, or gym. Just off the back of the studio is the newly installed outdoor sauna, making this an ideal wellness space. As the last house at the end of a private road, the acreage surrounding the home offers an atmosphere of stillness. The flat topography of the parcel is perfect for spending time outside among the mature trees and idyllic stone walls. A partially fenced-in area adds convenience, while the rest of the acreage is great for hiking and exploring. Conveniently located just outside the Village limits, the home is also only one mile from the Trailways bus to NYC. You are also moments away from the newly renovated Bearsville Complex, featuring two restaurants and the Bearsville Theater, as well as all of the dining, art galleries, and live music that Woodstock offers. Shown by appointment, this private sanctuary offering solitude and proximity truly captures the best of both worlds.
Courtesy: Four Seasons Sotheby's Int'l R
845-684-0084
Tucked away at the end of a quiet cul-de-sac in Woodstock, and set against a backdrop of woods, a gentle stream, and mountain views, this well-maintained home offers flexibility and income potential. The main residence features a welcoming living room, an eat-in kitchen, and a convenient half bath on the first floor. Upstairs, three bedrooms and a full bath provide a functional and comfortable layout, with hardwood flooring throughout. The lower level adds valuable living space with a spacious family room, complete with a pellet stove--perfect for cozy evenings. An attached one-bedroom apartment, with its own private entrance, is ideal for guests, extended family, or rental income. It features a full kitchen, bath, in-unit washer and dryer, and a charming three-season porch with skylights that fill the space with natural light. A rare opportunity to own a versatile property in a peaceful Woodstock setting, surrounded by nature yet close to everything the area has to offer.
Courtesy: Coldwell Banker Village Green
845-679-2255
Tucked into Woodstock's coveted Upper Byrdcliffe arts enclave, this thoughtfully built contemporary offers a rare combination of privacy, architectural character and effortless access to the village. Set on two acres with seasonal mountain views, the property blends modern comfort with artistic heritage in one of Woodstock's most sought after locations. The main house features 3 bedrooms and 2 baths, including an upstairs bedroom/flex room with plumbing already in place for an additional half bath. Filled with natural light, the home showcases dramatic wall-to-wall custom windows and sliders, soaring ceilings, exposed beams, and an airy open living space anchored by a modern wood burning stove and radiant heat for year-round comfort. Kitchen features custom cabinetry, large island with breakfast counter seating, and seamless flow into dining and living areas - perfect for entertaining. A wraparound deck and private balcony overlook landscaped grounds, gardens and a charming potting shed, creating multiple outdoor spaces to dine, unwind, and enjoy the peaceful surroundings. The primary bedroom opens directly to a private deck with an outdoor soaking tub designed for hot or cold plunges, creating a spa-like retreat immersed in nature. Mini-split heating and cooling, metal roof and custom windows add to the homes comfort and appeal. Adding exceptional versatility, the property also includes a sun/greenhouse room utilizing the reclaimed windows from the original artist studio. Additionally, there is a separate full 1 bedroom GUEST HOUSE complete with its own kitchenette and full bath - ideal for guests, extended stays, studio or passive income. Originally the studio of Woodstock artist and Woodstock School of Art founder, Robert Angeloch, the property has been thoughtfully transformed into a warm retreat while preserving the creative spirit and craftsmanship of the original space creating an opportunity to own a meaningful piece of Woodstock's history.
Courtesy: Halter Associates Realty
845-679-2010
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 hand built 1 Bd/ 2 Ba with additional flex room and art studio tucked away on 2 private acres on a dead end private lane in the hamlet of Shady speaks volumes. 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 the mountain overlooking Mt.Guardian he knew he was home. And there Calvin's own story with this land began. Calvin was from a. lineage of fine furniture makers and believed ''form follows function'' and as he hand built each part of his home he would go back to that philosophy. There was a 250 year old barn in Wilson State Park available for repurposing and there began the footprint of this unique, singular home. As Calvin did not have a sawmill he used an old time method of cutting the wood with a tool called an adz. And when we use the term hand built we mean it in the truest sense. He repurposed the wood and hand hewn beams from the barn as well as the Vosburg Turning Mill at the foot of Hutchin Hill, which are the framework of this light filled, warm home. Calvin used Chestnut hardwood floors throughout. He sourced plexiglass panels for the skylights from the Kingston Ford Dealership that they had used to build a dome to showcase their cars as he wanted to bathe the stairs in light. A friend told Calvin of an original cast iron sink that was available in Long Island and he drove down to get it. It is the centerpiece of his country kitchen with updated appliances but still the authentic feel in tact. Each frame, each corner, each board was carefully sourced over time. As Calvin described building the stairs he described it as an evolution with each step, without a plan but rather going back to the old adage ''form follows function''. And as every artist needs, he built a wall of windows south facing overlooking views of Mt. Guardian. Simultaneously he designed and built his studio with the same locally sourced materials where he would spend the next 50 years producing his art that can be seen all over the world. A bluestone walkway with rock outcroppings and a native plant pond connects the two structures. He mixed classic amenities like the clawfoot tub with more modern updates like the efficient mini splits throughout but still utilized his wood burning stove that is equipped to keep the whole home warm. Walking among his artwork and other artists who he has showcased on his land over the years, one feels like you are experiencing time in Woodstock that isn't easily accessible anymore. Calvin not only was a prolific artist but also an ardent environmentalist. He was on the forefront of helping to preserve Overlook Mountain and cherished the natural beauty the Hudson Valley offers.His land and the world he created here is a testament to that adoration. This home is truly one of a kind and just to walk it's land and it's rooms one feels the love and the craftsmanship. Minutes to the center of Woodstock yet a world a way. This property is the quintessential upstate sanctuary.
Courtesy: Halter Associates Realty Inc
845-679-2010
A bright and sunny Colonial gem just minutes into the center of Woodstock! This home is set far back and hidden from the road creating a true sense of privacy. Coming down the driveway, you begin to see the 1.47 acre yard wrapping around the house which is partially bordered by a charming stone wall. Once inside, the spacious living room is on your left with built-in bookcases and a fireplace with a wood burning stove insert. Directly in front of you is the main dining room with space for large gatherings. The bright and light kitchen is to the right with solid wood cabinets and quartz counters and a new stainless range, microwave and dishwasher. The large island is perfect for quick dinners, buffets, and homework! Off the kitchen is a bright breakfast room. Heading back to the dining room you pass a half bath. Once in the dining room, straight ahead of you is the inviting sunroom with huge windows looking out to the yard. This comfortable space has tons of room for a large plush couch for movie night! Sliders take you out to the very private yard. You step off the deck onto the paver patio and dining space to a large built-in fire pit for starry nights and s'mores. The custom gazebo has an overhead fan and electricity for lighting. There is a large trex deck built around an immaculate above ground heated salt water pool with sparkling waters. Enjoy a day swimming and grilling or just relax on the vast lawn and catch some rays. You are completely surrounded by dense foliage for the ultimate privacy! Next to a covered wood storage rack, there is a whole house stand-by generator for your peace of mind. Back inside, by the front door are the stairs that will take you to the four bedrooms. There is a sunny and spacious primary ensuite with a walk-in closet, a stand up shower, and three more roomy bedrooms and a beautiful hall bath. All the bedrooms have spacious closets. The hall bath has a walk in shower and a large soaking tub to relax with a good book. Back downstairs, there is a mudroom space coming in from the two car garage and a large open space ideal for all of your storage needs. The last place to see is the laundry room with yet more storage. If being just minutes into the center of Woodstock is not enough, this home is close to hiking, the rail trail, the Ashokan Reservoir and is a quick drive to the Thruway. Just beyond is Kingston which has many fantastic restaurants and shops! This home is a must see!
Courtesy: Serhant LLC
646-480-7665
Set on one of Woodstock's most coveted country roads, this classic home offers the rare combination of timeless charm, privacy, and an exceptional location. Just moments from the heart of Woodstock, yet quietly removed, Cooper Lake Road is known for its scenic beauty, peaceful surroundings, and idyllic walks to nearby Cooper Lake. Originally built in 1940 and renovated over the years, this 3-bedroom, 2.5-bath Colonial retains its period character while offering the comfort and ease of modern living. Tucked back off of the road, a private drive leads to the home, set on a generous 3.27-acre corner parcel with frontage extending to Rose Lane--survey available. Inside, the home unfolds with warmth and versatility. A welcoming den with built-ins and a powder room creates the perfect space for a home office or tv room. The living room is in part of the original house and features vaulted, beamed ceilings, a striking stone fireplace, and walls of windows. The kitchen is conveniently set between the attached garage and breakfast room that opens out onto a stone patio. A formal dining room is also off the kitchen. Upstairs, two guest bedrooms share a full bath, while the grand and spacious primary suite enjoys its own private wing, complete with built-ins and an ensuite bathroom. This is a rare opportunity to own a truly special home in one of Woodstock's premier locations--where quiet country roads, natural beauty, and proximity to town come together seamlessly.
Courtesy: BHHS Hudson Valley Properties
845-679-0006
Public Remarks: TURNKEY WOODSTOCK COTTAGE. A deep violet front door opens to a rustic ''mudroom'' with a bluestone floor and a closet for your outdoor gear. The kitchen, with its Liebherr and Bosch appliances, custom cabinetry with pantry, stylish lighting fixtures, radiant heat, beamed ceiling with a skylight - leads into a light-filled Living/Dining/Den space with original wide-plank wood floors, ceiling fan and sliders that open to a covered deck, a patio and the gorgeous grounds beyond. To the left, a spacious sunlit Family Room with a large bluestone hearth, an exposed beamed ceiling and an original Dutch door that provides easy access to the deck for firewood and the great outdoors. The two bedrooms - one with a full bath and the other with a half bath, laundry, walk-in closet and an attic loft for storage are located on opposite sides of the home, ensuring privacy and space. Hardwood floors prevail throughout this single level cottage. The 1.56 acre property is an unexpected surprise. Level, landscaped lawns flank each side of the home and mature trees provide character and beauty. The expansive backyard has a bluestone patio, fire pit and covered BBQ area with outdoor lighting - all within view of a garden with ''great bones'' and a built-in irrigation system that awaits revival. 1/4 acre of wilderness offers exploration with its ''magic forest'' vibe and 2 wooden bridges span a former stream. You really feel transported - right there on Tinker Street in Woodstock. Your pets will love it too! Tucked into the property are 2 attached storage sheds and a sturdy lean-to with a cement floor for yard equipment, etc. The larger shed has windows, electric and the potential for a studio to support creative and wellness activities. A standby Generac generator is invaluable for peace of mind. The metal roof and galvanized gutter system will protect the home for years to come. The driveway accommodates 4 cars. On the Trailways Bus route, steps from Sunfrost Market for treats, groceries and its delightful, soon-to-reopen café/juice bar. Walk to Woodstock Spa for pampering or a workout or take a 15-minute stroll to the center of Woodstock with its shops, restaurants, galleries and lively music scene. A 15-minute drive to Kingston or Saugerties. What a convenient, easy to maintain getaway or full-time home!
Courtesy: Berardi Realty
845-201-1111
Just a half mile from the center of Woodstock, this bucolic 3.7-acre compound offers a rare blend of architectural charm, natural beauty, and versatile living. The property includes the main house and two outbuildings, a one-bedroom cottage and a studio with an attached three-bay garage. Bedroom and bath layout described as the primary residence having three bedrooms and three full baths measuring 2200 sq. ft. The detached cottage has one bedroom with one full bath measuring 480 sq.ft and the detached studio has another full bath measuring 400 sq ft. The main house is a light-filled classic Woodstock modern home built around the original Woodstock's artist's cabin. Thoughtfully designed to frame the surrounding forest through expansive glass sightlines, allowing for views of deer, birds, and other wildlife throughout the seasons. Inside, the home showcases unique historical details such as chestnut beams in the dining room, a bluestone fireplace, a built-in library, and a mix of slate, Spanish tile, pine, and oak flooring. The multi-level living area features a lofted tongue-and-groove wood ceiling and five architectural skylights that bring the outdoors in. Upon entry, you're greeted by a bright and inviting sunroom that opens into a formal foyer. Just off the foyer is a room that can serve as a home office, reading nook, or playroom, conveniently located next to a full guest bathroom. This level also features a cozy bedroom and a hallway office nook--perfect for remote work or quiet study. The eat-in kitchen includes a charming breakfast nook that offers serene views of the surrounding landscape and seamlessly flows into the dining room, creating a warm and inviting connection between the spaces. The dining area doubles as a music room, enhanced by vintage wide-plank pine flooring and a wood-burning fireplace that adds warmth and character. Step down into the sunken living room, where high ceilings and built-in bookshelves create a bright, welcoming space ideal for relaxing or entertaining. The primary suite features an en-suite bathroom with Parisian influences, including a bidet and a deep, one-person soaking tub with jacuzzi jets. Sliders walk out to the private multi-level deck and your own private atrium. Just off the main area, a newly designed mason-laid bluestone patio features a seamless transition into an expansive deck, offering the perfect setting for quiet evenings or vibrant dinner parties. The second floor features a loft area, ideal as a TV or family room, providing a comfortable space to relax or entertain. Tucked away for privacy, the second primary suite includes a full bath, creating a serene retreat separate from the main living areas. The one-bedroom cottage evokes the feel of an English guesthouse, with wood floors, a full kitchen and bathroom, and its own dedicated utilities, making it a wonderful space for guests or potential rental income. The detached studio, adjoining the three-car garage, feels like a New York City loft, complete with wide-plank floors, an open-concept layout, a bathroom, and a kitchenette. With its own electric and utilities, the space lends itself well to use as an office, yoga or art studio, or another income-producing rental. The garage offers three bays--two for vehicles and one ideal for workshop or storage use. For decades, this special property has been a gathering place for artists, musicians and writers. The home is designed to inspire and connect, all within minutes of Woodstock's vibrant center. It's an exceptional retreat with comfort, character, and potential in every direction. Please see addendum for recent updates and improvements on the home.
Courtesy: Grist Mill Real Estate
845-246-3200
Totally private two bedroom and two bath contemporary home bordering 44 acres of DEP protected land. Just off Mink Hollow Road in the hamlet of Lake Hill. Drive down long driveway to discover an artesian spring pond, garden beds, perennials and forest. Main living area on first floor includes open kitchen, dining and living room. Breakfast bar, wood cabinets and custom tile backsplash with window over kitchen sink. Primary bedroom located upstairs is a large open space with a deep soaking tub in the bathroom, office and sitting area with sky light and walk in closet. Huge studio space with high ceilings is located between the two main living spaces has tall wood Douglas Fir French doors and fixed panel letting in the natural light. Third and final section of the home consists of front to back living space upstairs currently being used as a healing room. Large storage area below this room with built in shelves. Possibilities in the home are endless with the large open spaces. Enclosed screen porch overlooks fenced in yard. Situated on 3 plus acres on a dead end street bordering state land makes this property a rare find. The Trailways bus stops at the end of Mink Hollow Road to get to NYC in 2 hours. Village of Woodstock is a short drive. Enjoy the hiking trails at the end of Mink Hollow Road that take you deep into the Catskill Mountains along the Beaverkill stream. Serenity awaits at 4 Ashley Lane.
Courtesy: Compass Greater NY, LLC
914-238-0676
Tucked into a quiet cul-de-sac, this spacious 4-bedroom, 2.5-bath Colonial features a gorgeous in-ground swimming pool surrounded by mature plantings. With a comfortable, easy flow, a welcoming foyer opens to a bright main level that connects the living room, dining area, and updated kitchen. The kitchen is equipped with granite countertops and stainless-steel appliances, while the bathrooms have been tastefully updated, including a primary suite with a jetted tub. Just beyond the main living space, a spacious second living room with cathedral ceilings and a classic brick wood-burning fireplace offers a cozy place to relax or set up a home office. A screened-in porch provides a comfortable retreat in the warmer months, overlooking the beautifully landscaped backyard. Outside, the property truly shines with an 18' x 36' heated in-ground pool surrounded by bluestone decking making it ideal for summer entertaining. Mature plantings and fully fenced grounds create a private, garden-like setting. Practical features include a first-floor mudroom with washer and dryer, generous hallway closets, and a convenient half bath with easy access to the pool. Upstairs, the primary suite offers a spacious closet along with three additional bedrooms and two updated bathrooms. The full basement provides excellent storage, and a large shed in the front yard adds space for garden equipment. With thoughtful updates, well-maintained systems, and a layout that balances privacy with convenience, this home is ready to enjoy year-round.
Courtesy: Coldwell Banker Village Green
845-679-2255
Here in the heart of Woodstock Village, this lovingly updated home strikes a rare balance between privacy and town-center convenience on a peaceful dead-end road. Stroll to shops, yoga studios, restaurants, and the NYC bus, then return to a private garden retreat. Light-filled and airy bungalow-style home with a loft-like flow, arranged for flexible living, with a bedroom and full bath on each level. Large windows capture the sky and the surrounding yard, flooding the interiors with natural light and creating a strong connection to the outdoors. A 2020 reconstruction of the second floor introduced a generous primary suite with vaulted ceilings, wide-board pine floors, a walk-in closet, a full bath, and a private deck built to accommodate a hot tub or a future conversion into a four-season sunroom or studio. The ground-floor bedroom offers direct access to a deck and the fenced backyard. The main level balances form and function with a Bertazzoni gas range, Bosch dishwasher, porcelain double sink, and custom wood countertops, all paired with warm materials and clean, unfussy lines. Refinished pine floors run throughout, while the expanded guest room includes a custom-built-in birch desk thoughtfully integrated into the home's original footprint. Comfort and efficiency are addressed by split-system heating and cooling on both levels, while a Jøtul propane stove installed in 2023 adds warmth and atmosphere. Connected to public water and sewer, the property offers low-maintenance village living. Recent improvements include a new roof in 2020, a complete exterior repaint in 2024, and new gravel added to the driveway and side patio in 2025. Outside, the fully fenced backyard is framed by mature plantings, including flowering cherry and boxwood, along with two cedar raised garden beds. Two outbuildings add flexibility, one serving as storage and the other well-suited for studio or workspace use. Custom cedar shelving adds both utility and charm to the space. Understated and refined, this village home offers immediate access to town while maintaining a genuine sense of retreat in one of Woodstock's most peaceful settings.
Courtesy: Howard Hanna Rand Realty
845-338-5252
Situated on a large level lot and a quiet road near the heart of town. Some recent updates and fresh paint make this 4 brdm ranch home a terrific find in today's market. A covered porch in the front and rear allow for convenient outdoor entertainment. There is also plenty of off street parking and a detached shed for additional storage. Central location just minutes to Woodstock's vibrant music scene, restaurants and shops. Close proximity to a public park, hiking and biking trails, skiing and golfing. A few more personal upgrades will make this gem shine even more.
Courtesy: Coldwell Banker Village Green
845-679-2255
Tucked away at the end of a quiet dead-end road, just minutes from the center of Woodstock, 9 Chesters Place is the kind of home buyers ask for but rarely find. Lovingly maintained by two resident artists, the house reflects careful, creative stewardship and thoughtful details throughout. The home is nearly new, mindfully designed, and set in a peaceful, private setting. This bright, beautiful home is surrounded by trees in back giving it a year round woodsy feeling. Built just nine years ago, this single-level residence offers the ease of modern construction paired with a warm, inviting feel. Inside, 9-foot ceilings and beautiful natural light create an airy, uplifting atmosphere throughout. The open-concept living spaces are effortless and functional--perfect for both everyday living and hosting friends. Three bedrooms and two full baths provide flexibility for guests, a home office, or simply room to spread out. Enjoy a dedicated laundry room for convenience and organization. What truly sets this home apart is how seamlessly it connects to the outdoors. An expansive deck extends your living space, offering the perfect spot for morning coffee, summer dinners, or quiet evenings surrounded by nature. Low-maintenance by design, this is a home that allows you to focus on enjoying your surroundings rather than managing them--ideal as a full-time residence or a weekend escape.The garage currently houses an artist's workshop occupying half the space -- perfect for creative projects, studio use, or easy conversion to additional storage or parking. This offering captures what so many are seeking right now: simplicity, scenery, artistic charm, quality, and a location that feels tucked away--yet close to everything that makes Woodstock so special. A 3D Walkthrough Tour is available in the digital Lookbook or by request.
Courtesy: BHHS HUDSON VALLEY PROP-WDST
845-679-0006
Discover your Upstate sanctuary in this contemporary 3-bedroom, 1.5-bath gem on Ohayo Mountain Road. Nestled in wooded bliss on 1.8 acres and in close proximity to protected state land, this home delivers a rare sense of peace and enduring natural beauty. Gleaming hardwood floors, a cozy wood-burning stove, and an open-concept floorplan perfect for modern living. Step outside to your private deck, ideal for entertaining or simply soaking in the tranquil forest surroundings. Less than 20 minutes from the vibrant charm of Woodstock, Phoenicia, and Kingston, and under 30 minutes to the Rhinecliff train station for seamless access to the city, this haven is a dream for nature lovers, creatives, or anyone seeking peace of mind. Your cozy, nature-embraced escape awaits. Schedule a tour soon!
Courtesy: Corcoran Country Living
845-684-0304
Set beside one of Woodstock's most treasured and enduring landscapes, this quintessential Woodstock property unfolds along the edge of the Thorn Preserve--a protected 60-acre expanse celebrated for its sweeping open grasslands, riparian forest, ponds, and the most artist-captured views of Overlook Mountain. Even more remarkable, this landscape is permanently conserved, ensuring that the uninterrupted meadow vistas and natural beauty surrounding the property will remain untouched for generations to come. Positioned adjacent to this beloved preserve, the property itself feels deeply connected to its setting. At the heart of the land sits a circa 1875 cottage, rich with history and timeless charm. The 2-bedroom, 1-bath main house is defined by its inviting and authentic character, where every space feels intentional and grounded in warmth. The living room centers around a classic wood stove, creating a natural gathering point and an atmosphere that is both cozy and nostalgic--perfect for long winter evenings or relaxed weekends in the mountains. The interiors carry a sense of understated simplicity, where cottage-style living takes precedence--intimate yet functional, with a layout that flows easily from room to room. Each bedroom offers a quiet retreat, framed by views of the surrounding landscape and softened by natural light filtering through mature trees and open meadow beyond. The home's charm lies not only in its age, but in its connection with nature and serene interiors --perfectly embodying the spirit of classic Woodstock living. A covered front porch extends the living space outdoors, overlooking the meadow and toward the preserve beyond. It's an ideal setting for morning coffee, slow afternoons, or evening gatherings--where the landscape becomes a constant backdrop, shifting beautifully with the seasons. Complementing the main residence is a thoughtfully designed, stand-alone modern ADU that introduces a refined architectural contrast while maintaining a seamless connection to its surroundings. Clean lines and a minimalist sensibility define the space, creating a bright, open studio layout that feels both elevated and effortless. Inside, the ADU is anchored by a wood stove in the living area, adding warmth and texture to the modern design. The full bathroom is well-appointed, while a lofted storage area maximizes functionality without compromising the open feel of the space. The design prioritizes light, warmth, and connection to the outdoors--making it equally suited as a guest house, artist's studio, or private retreat. The ADU's private deck is a true highlight--positioned to overlook the Thorn Preserve and capture its most captivating perspectives. From sunrise to golden hour, the ever-changing sky and expansive meadow views create a setting that feels both inspiring and deeply calming. Together, the historic cottage and modern ADU form a rare and harmonious compound--blending old-world charm with contemporary design, all set against one of Woodstock's most iconic and permanently protected landscapes. Whether used as a full-time residence, weekend retreat, or flexible live/work environment, this property offers a lifestyle defined by beauty, privacy, and enduring connection to nature.
Courtesy: Coldwell Banker Village Green
845-679-2255
Tucked at the end of a quiet cul-de-sac in Woodstock, this bright, single-level ranch offers a great opportunity for a buyer ready to renovate and make it their own. Set on a 0.24-acre lot with a level backyard, the property enjoys a peaceful setting just minutes from the center of town. The home offers 849 square feet with 2 bedrooms and 1 bath. In addition to the main living room, the layout includes a separate room that can serve as a second living area, office, or guest space. Its straightforward layout and single-level living make it an appealing option for someone looking to update a home to suit their own style and needs. Listed below assessed value to reflect the work needed, this is a property with clear upside for a buyer with vision. Whether as a full-time residence, weekend getaway, or investment opportunity, the location provides a strong foundation. The property is being sold ''as is'' and, due to its condition, may not qualify for conventional financing. Cash buyers preferred.
Courtesy: William Pitt Sothebys Int Rlty
845-677-9822
Experience the legacy of Woodstock through this extraordinary historic offering. Once home to the iconic Woodstock Lodge and The Pinecrest, this storied 6.5-acre property offers a unique opportunity to reimagine a legacy estate in one of the Hudson Valley's most sought-after destinations. Set on scenic, gently rolling land with a blend of open clearings, wooded trails, and a seasonal stream, the property provides both privacy and proximity. Situated just a short distance from Woodstock's vibrant village center; known for its charming shops, acclaimed restaurants, and year-round arts and cultural events. The site includes nine existing structures, an additional foundation, a workshop, and an in-ground gunite pool, offering a wide range of possibilities for restoration, redevelopment, or a thoughtfully designed residential compound. Existing utilities, wells, and septic systems are in place, providing a strong starting point for future plans. Currently zoned R3 Residential, the property presents potential for residential redevelopment and possible subdivision (buyer to perform due diligence regarding future use, zoning, and configuration). Property and all structures and infrastructure are being sold as-is, where-is. A rare opportunity to steward a historic Woodstock property and bring a new vision to life in one of the Catskills' most legendary locations.
Courtesy: Howard Hanna Rand Realty
845-338-5252
Tucked away on a peaceful, wooded lane, this inviting home offers the perfect blend of privacy, space, and convenience- just minutes to the heart of Woodstock. Inside, the home opens to an expansive living room anchored by a beautiful brick fireplace, creating a warm and inviting centerpiece for gatherings or quiet evenings. This oversized space includes a full bathroom and flows effortlessly to a private outdoor deck, extending your living area into the surrounding landscape--perfect for morning coffee, and or entertaining under the trees. Natural light fills the interiors, enhancing the home's relaxed and welcoming feel. A spacious kitchen with ample room for cooking and entertaining. The flexible layout includes 3-4 bedroom ideal for guests, remote work, or weekend hosting. The primary bedroom offers a peaceful retreat, complete with a walk-in closet area that presents a unique opportunity--perfect as a nursery, dressing room, or private home office. Step outside and experience your own secluded haven, surrounded by mature trees and the tranquility that defines the Woodstock/Hurley area. Whether used as a full-time residence, weekend escape, or income-producing property, this home captures the essence of upstate living. Located just minutes from the vibrant village center--known for its boutiques, galleries, live music, and creative energy--this is a rare opportunity to own in one of Woodstock's most sought-after areas. This location offers the very best of living in the Catskills-where nature, culture, and community meet. A true retreat with space to gather, room to grow, and a lifestyle to fall in love with. Make an appointment today!
Courtesy: Keller Williams Hudson Valley
845-481-2700
Welcome to The Waterfall House, a truly rare offering nestled in the heart of Woodstock Proper, where nature, creativity, and privacy converge in the most enchanting way. Being offered for the first time, this storied 3,023 sq ft brick colonial is more than a home; it’s an experience, a retreat, and an open canvas for your vision to unfold. Set on nearly 12 acres of lush, mature landscape, the property invites you to slow down and reconnect. Inside, you’ll find expansive, light-filled living spaces, six legal bedrooms, and three and a half bathrooms, each room waiting to be reimagined into something extraordinary. The sun-drenched rear room is where the magic truly begins. Walls of windows blur the line between indoors and out, immersing you in the sights and sounds of nature. Open the windows and let the rhythm of your private waterfall and babbling brook become your daily soundtrack, equal parts calming, inspiring, and unforgettable. Step outside into your own private woodland to explore, create, or simply unwind. Nearly 12 acres of this kind of privacy in Woodstock Proper is a rare offering. The sweet soul of this property are two charming artist cabins, each offering one bedroom and one full bathroom, perched right along the water’s edge, with one cabin offering 885 square feet and the other 740 square feet. Once home to local creatives, these cabins carry a palpable energy, perfect for studios, guest retreats, or a continuation of their artistic legacy. This is not just a home, it’s a place for visionaries, nature lovers, and those seeking something deeply special. A once-in-a-lifetime opportunity to own a property that feels both grounded and magical, private yet inspiring, where every day begins and ends with the sound of water and the beauty of the land, an experience that feels worlds away, yet right at home.
Courtesy: Compass Greater NY, LLC
845-334-0227
Stylish, single-story living: This fully reinvented bungalow is convenient to both Woodstock and Kingston, and features large over-sized rooms and systems, all in a tight semi-open layout that takes full advantage of its over-sized 2+ acre wooded parcel. Grounded by hardwood or polished-concrete floors throughout and topped by dramatic cathedral ceilings in most rooms, the house features two main living spaces - a large living and dining space anchored at one end by a bluestone fireplace and at the other by a renovated kitchen; plus a separate family room with a wood-burning stove and sunny side foyer. The huge oversized primary bedroom features its own en suite spa-like bathroom with an open shower plus a soaking tub with its own picture window overlooking the wooded backyard. A separate work or den area adjoining the primary suite could provide additional sleeping space, or a home office or studio. An additional bedroom features its own en-suite renovated bathroom. Oversized windows take full advantage of the wooded surroundings. The house is set back generously from the road and includes a large detached garage, plus plenty of front-yard space to enhance your privacy with additional trees or other landscaping.
Courtesy: Halter Associates Realty Inc
845-679-2010
Inside Swoop House there is a versatile floor plan that includes four en suite bedrooms, one an attached guest suite, and two two-story great rooms, one of which was designed as a professional art studio. Designed by FT Architecture & Interiors and inspired by the Diller Scofidio Slow House, two non-parallel curved walls and sloping ceilings create a graceful series of shapes. This singular residence is sited at the end of a long driveway on Overlook, having 16 peaceful and private acres. This property provides you with both distant and intimate mountain views. It borders thousands of acres of pristine NY State land, while being located just five minutes from the village of Woodstock. The first story has a spacious two-story entry with a walk-in closet and Brazilian cumaru wood flooring. There is a great room with a 40-foot-long curved northern wall providing ample room for art displays, as well as a row of 10 large picture windows above. The room is anchored by a wood burning fireplace with a 15-foot blanca perlino Italian marble hearth. Floor-to-ceiling windows face South, where glass doors lead to a walkway and a series of outdoor spaces. The gourmet kitchen boasts top of the line Bosch and Wolf appliances, as well as a built in Sub-Zero refrigerator, a stone countertop, and a butler's pantry with a sink and a second refrigerator. The kitchen door leads out onto an expansive two story screened porch designed for dining and lounging, and the 40-foot outdoor deck, with black locust wood decking, where you can host dinner parties among the treetops. Two of the four well appointed en suite bedrooms are located on either end of the first floor. One has a walk-in closet, and a private entrance that opens out onto one of several native bluestone patios, surrounded by perennial gardens with a hot tub. Its spacious bathroom has a dressing area and an oversized Brazilian stone shower. Adjacent to the kitchen and the screened porch is a second bedroom with adjoining full bath. Leading to the primary bedroom suite, an open staircase provides views of the great room and outdoors from above. At the top of the stairs there is access to a south facing balcony. Here you can soak up sunshine and views year round while staying protected from the elements. The primary bedroom suite has two walls of floor to ceiling windows, a walk-in closet, an ensuite bathroom with a shower, and a walk-through room for a jetted tub. From here one can step outdoors onto a serene sleeping porch on a loft within the two-story screened porch. The private guest suite, the second great room/studio, and the media room can be accessed from the inside as well as outside on the ground level via its own dedicated driveway. This space currently boasts a versatile loft like floor plan, with open partitioning that can easily be reconfigured to meet various needs. The fourth bedroom suite has a full bathroom that includes an oversized steam shower containing an elegant curved stone bench. There is also room for home offices, and has a private entrance that opens to a bluestone patio. The second great room is currently in use as a painting studio. It has 18-foot-tall ceilings, a 40-foot-long display wall, tracks for lighting, oak flooring with radiant heat, and a double utility sink in the kitchenette. Glass double doors and large windows with custom sun-blocking shades provide gorgeous natural light. The adjoining media/family room with built-in bookcases is a place where you can refresh, listen to music, have meetings, workout, or relax. Also on this level is a laundry room and a 350 square foot heated storage space. The outdoor spaces where you can enjoy the mountain and gardens are perfect for finding solitude or for entertaining. Swoop House is within 10 minutes to The Bearsville Theater, Woodstock's renowned restaurants, music venues, art galleries, shops, and farmer's market. It is 20 minutes to Kingston, 30 minutes to Rhinebeck and 2 hrs to NYC.
Courtesy: eXp Realty
888-276-0630
A truly one-of-a-kind residence and rare opportunity, this exceptional home offers a seamless blend of architecture and art in the heart of Woodstock, walking distance to Tinker Street, yet set privately on 1.73 secluded acres just minutes from the village. Designed as a fusion of a Frank Lloyd Wright–inspired contemporary addition and an original Buckminster Fuller–style geodesic dome, the property delivers over 3,300 sq. ft. of light-filled living space with remarkable character and a spacious, flexible layout ideal for both everyday living, work-from-home, and the Hudson Valley lifestyle. Open hardwood floors, soaring Douglas fir ceilings, and walls of windows create an effortless indoor–outdoor flow overlooking the natural landscape. A lofted gallery office leads to the primary suite with private gas stove, steam shower, dual vanities, and a generous walk-in closet. Two well-appointed bedroom suites in the downstairs wing, including two additional guest bathrooms on the lower level, the home offers privacy and comfort for residents and guests alike. Each lower-level suite features direct access to the outdoor space and stone patio. The original dome includes a separate entrance, full bath, modern kitchen, and wood-burning stove, ideal for a studio, guest space, or additional living area. A Central Park–style gazebo and mature grounds complete this serene setting. Embrace the luxury of living within walking distance to Woodstock’s renowned dining, galleries, and music venues while maintaining exceptional privacy. A rare offering in what is truly a one of a kind home.
Courtesy: Coldwell Banker Village Green
845-679-2255
Welcome to 18 Country Club Lane. Located less than half a mile from the picturesque Village of Woodstock, this thoughtfully reimagined property offers easy access to shops, restaurants, fitness studios, playgrounds, and nearby nature trails, all just minutes from your front door. Designed by architects, the half-acre property includes two buildings and blends comfort, character, and modern updates with care. The main house opens to a fully enclosed, sun-filled porch, ideal as a mudroom or flexible entry space. Inside, the updated living, dining, and kitchen areas are unified by exposed beams, vaulted ceilings, and knotty pine details, creating a warm, inviting atmosphere. The open kitchen is both stylish and functional, featuring quartz countertops, custom cabinetry with generous storage, high-end appliances including a dishwasher and smart refrigerator, and a dedicated pantry or coffee bar. Oversized picture windows frame the surrounding woods and offer seasonal mountain views, bringing the outdoors in. Two well-proportioned bedrooms feature vaulted ceilings, custom closets, and adjacent bathrooms. Both bathrooms have been tastefully redesigned, with the primary bath offering terrazzo tile, a double-sink vanity, an en-suite soaking tub, and a walk-in shower. Adjacent to the main house is a year-round studio building, well-suited for a home office, art or music studio, or flexible creative space. The studio includes cabinetry, a refrigerator, and two separate rooms, with potential to add a bathroom and water, subject to town approval. This is a rare opportunity to enjoy privacy and thoughtful design within a vibrant community. The property is also conveniently located near Kingston and Saugerties, and offers easy access to the Catskill Mountains for winter recreation, hiking, and fishing, making it an ideal full-time residence or retreat in the heart of the Hudson Valley. A 3D Walkthrough Tour is available in the digital Lookbook or by request.
Courtesy: Four Seasons Sotheby's Int'l R
845-684-0084
Fall in love with this artfully reimagined and expanded 1930 farmhouse, privately set on a gentle hill just moments from the heart of Woodstock. Rich in history and character, this special home was once owned by Michael Lang, the legendary founder of the 1969 Woodstock Festival—adding a rare and meaningful connection to the town's iconic past. Thoughtfully renovated, the home offers a beautiful balance of vintage charm and modern convenience. A stunning new open-concept addition features dramatic vaulted ceilings and walls of windows that flood the space with natural light and open seamlessly to a welcoming porch—perfect for entertaining or quiet moments surrounded by nature. The flowing floor plan is ideal for today's lifestyle and effortless gatherings. The chef's kitchen is beautifully appointed with a large center island offering seating, abundant storage, and a layout designed for both everyday living and entertaining. The main level primary suite features a new ensuite bath, fireplace, and peaceful views. Upstairs, you'll find an additional full bath and a second ensuite bedroom, also offering lovely views. Throughout the home, creative and distinctive tilework adds artistic flair, reinforcing the seamless blend of contemporary design and original farmhouse character. A separate guest cottage sits close to the main residence and offers exceptional flexibility—configured as a living room and bedroom or two private ensuite bedrooms, complete with a sauna. Ideal for guests, extended family, or creative use. A truly unique Woodstock offering—steeped in history, thoughtfully updated, and perfectly located just minutes from town.
Courtesy: BHHS Hudson Valley Properties
845-679-0006
Set on nearly 9 serene acres in the heart of Woodstock's historic Byrdcliffe Arts Colony is a rare synthesis of architectural precision and natural harmony—an embodiment of award-winning architect John Storyk's deep understanding of space, sound, and site. Designed in 1969 at the very beginning of Storyk's now-legendary career—just after his groundbreaking work on Jimi Hendrix's Electric Lady Studios and the famous Bearsville Theatre—this redwood-clad contemporary home reflects his signature style: intuitive flow, warm natural materials, and an architect's sensitivity to both form and function. The 4 BR, 4 Bath, 4,000+ sq ft (includes guest/pool house) single family home is privately sited with a pond, heated in-ground salt water, gunite pool, and massive guest/pool house. This Mid-Century Modern sanctuary is defined by its soaring ceilings, custom mill work, and an organic relationship with the surrounding landscape. Every room is bathed in natural light through walls of glass, and oriented to maximize the surrounding views of meadow, woods, and sky. A dramatic curved, sunken living room—anchored by a large brick fireplace—evokes the sensorial immersion typical of Storyk's performance spaces. Here, spatial geometry and acoustics are not incidental but essential; offering not just a place to live, but a place to listen and feel. At the heart of the home is a Poggenpohl kitchen—a clean, functional workspace designed with the home chef in mind—that opens to dining and gathering areas which flow out effortlessly to the screened porch, expansive decks, landscaped gardens, and tranquil pond beyond; all designed to foster serenity and creative inspiration. Every line and threshold reflects Storyk's belief that architecture should support creativity and calm—never compete with it. Private spaces include a luxurious first floor primary suite and a guest apartment (with its own entrance) featuring a kitchen, full bath, and private deck—ideal for hosting, creating, or retreating. Across the entire property the interior volumes are balanced by exterior spaces with curated meadows, and reflective water elements including the large, heated, salt water, in-ground, Gunite pool) all reinforcing the idea of the house as an instrument tuned to its environment. While John Storyk is globally known for acoustically perfect studios and world-class performance venues, this home reveals another side of his genius: the quiet artistry of domestic space, where light, proportion, and stillness are as important as sound. A residence like this—designed by one of the 20th century's most innovative architectural minds, and located in a cultural enclave as storied as Byrdcliffe—is a truly singular offering. 289 Upper Byrdcliffe Road is not just a home, but a living, resonant experience—thoughtfully conceived, masterfully built, and deeply rooted in the creative spirit of Woodstock. Please note: Additional town-approved plans exist for a separate structure with its own septic and driveway entrance. All this coalesces to make an extraordinary compound with limitless options for a life well lived.
Woodstock is located in New York. Woodstock, New York has a population of 6,215. Woodstock is less family-centric than the surrounding county with 20.17% of the households containing married families with children. The county average for households married with children is 25.39%.
The median household income in Woodstock, New York is $66,181. The median household income for the surrounding county is $71,040 compared to the national median of $69,021. The median age of people living in Woodstock is 60.2 years.
The average high temperature in July is 83 degrees, with an average low temperature in January of 12.3 degrees. The average rainfall is approximately 48.2 inches per year, with 51.1 inches of snow per year.
