Courtesy: Frank Lumia Real Estate Plus
845-586-4486
Woodstock Condo at Maverick Knolls Discover an exceptional opportunity to own a single-level corner condo in the desirable Maverick Knolls community of Woodstock, NY. This bright and airy residence combines convenience, modern updates, and the natural beauty of the Catskills, making it ideal for year-round living or as a low-maintenance retreat. The home has been refreshed with all new appliances and freshly painted interiors, giving you a turnkey space that is both functional and stylish. The corner placement brings added privacy, abundant natural light, and scenic views of the well-tended grounds. With a single-level layout, the home is designed for ease of living and accessible comfort. Maverick Knolls is known for its beautifully maintained landscape and its sense of community. Amenities include a seasonal pool, perfect for summer relaxation, and well-kept tennis and pickleball courts, providing recreation steps from your door. The grounds are landscaped with care, echoing the natural beauty of the surrounding mountains. Location is a key advantage. Maverick Knolls is just minutes from the heart of Woodstock, where galleries, music venues, cafes, and restaurants capture the area's rich cultural heritage. Outdoor lovers will appreciate nearby hiking trails, scenic overlooks, and year-round opportunities to enjoy the Catskills. Access to the New York State Thruway is straightforward, allowing easy trips to and from New York City, Albany, and beyond. This property offers the best of both worlds: a quiet and well-kept home within a community that values leisure and connection, paired with proximity to one of the Hudson Valley's most celebrated towns. Whether you are seeking a full-time residence, a weekend escape, or an investment opportunity in an established community, this condo delivers comfort, convenience, and a true Woodstock lifestyle.
Courtesy: Coldwell Banker Village Green
845-679-2255
Tucked away on a quiet, tree-lined lot, this sun-filled 3-bedroom ranch offers privacy, versatility, and an enviable location, just a short drive from both Woodstock and Kingston. A classic brick-and-wood-paneled facade sits proudly atop a gently sloping lawn, surrounded by mature hardwoods. Inside, an open, airy layout connects the kitchen, dining area, and living space. Warm hardwood floors flow throughout the main living areas, and large windows bring in abundant natural light. The kitchen features maple cabinetry, stainless steel appliances, a center island with generous prep space, and tile flooring. Outside, the property's standout feature is a spacious studio/office attached to the garage and just ten feet from the main house, perfect for a home business, art studio, guest space, or work-from-home retreat. The two-car garage includes a built-in workshop or creative area, plus plenty of room for tools, storage, and projects. A paved driveway offers ample parking. Peace of mind comes standard with a whole-house generator to keep you comfortable through any storm. A well-located home with room to work, create, and unwind.
Courtesy: Coldwell Banker Village Green
845-679-2255
Tucked away on a quiet, tree-lined lot, this sun-filled 3-bedroom ranch offers privacy, versatility, and an enviable location, just a short drive from both Woodstock and Kingston. A classic brick-and-wood-paneled facade sits proudly atop a gently sloping lawn, surrounded by mature hardwoods. Inside, an open, airy layout connects the kitchen, dining area, and living space. Warm hardwood floors flow throughout the main living areas, and large windows bring in abundant natural light. The kitchen features maple cabinetry, stainless steel appliances, a center island with generous prep space, and tile flooring. Outside, the property's standout feature is a spacious studio/office attached to the garage and just ten feet from the main house, perfect for a home business, art studio, guest space, or work-from-home retreat. The two-car garage includes a built-in workshop or creative area, plus plenty of room for tools, storage, and projects. A paved driveway offers ample parking. Peace of mind comes standard with a whole-house generator to keep you comfortable through any storm. A well-located home with room to work, create, and unwind.
Courtesy: Coldwell Banker Village GreenK
845-331-5357
Here is the rare opportunity to own in Maverick Knolls, Woodstock's only townhouse community. Located minutes from the Village of Woodstock, this charming home pairs hardwood and quarry tile floors with tumbled marble countertops, all set in a lovely location overlooking the pond. Take in the natural beauty from your private deck. The dining and living rooms showcase design elements by Dominique Vos, with stunning beams and arches that evoke the feel of a Spanish villa. Central A/C keeps you cool in summer, and major updates are already done, with a 2-year-old HVAC system and a 3-year-old roof. Woodstock's fabled shops and restaurants are just minutes away. Furnishings are available for purchase, excluding the living room coffee table and mirror. Come see it for yourself and be delighted.
Courtesy: Coldwell Banker Village Green
845-679-2255
History abounds at this remarkable estate, reached by a quarter-mile-long drive offering complete seclusion across 43+ acres spanning two parcels. Sited below the slopes of the historic Byrdcliffe Arts Colony and adjacent to the legendary Grossman estate, the property offers a rare combination of privacy, natural beauty, and Woodstock history. The property features three main buildings: a charming storybook 1934 cottage with two bedrooms and two baths; a three-bay garage with a second-floor office; and the original barn, now converted to a two-bay garage. Completing the structures is a tool and potting shed adjoining a stone patio with a stone fireplace. Inside the cottage, an expanded eat-in kitchen features sliders leading to a stone terrace overlooking the pond and mountains. The beamed-ceiling living room centers around a fireplace, with French doors capturing the surrounding views. The primary en-suite bedroom features original painted woodwork, an enclosed daybed, and another fireplace. Upstairs, a cozy second bedroom with mountain views completes the cottage. Up the hill sits the Woodstock Recording Studio, where Jack DeJohnette, Happy Traum also Blood Sweat and Tears and The Band recorded their Gold Albums. The spacious, heated, vaulted studio features sound booths and shares the structure with an adjoining office and vault. The heated, oversized three-bay garage, with loft space and an upstairs office, overlooks the pool area below and offers additional views of the meadow, pond, and mountains. Down the lawn and through the meadow lies the magical pond, surrounded by nature and mountain views. This is a truly special piece of Woodstock history - and a little slice of paradise.
Courtesy: Coldwell Banker Village Green
845-679-2255
Set well back from the road and sited on 4+ acres, this wonderful 1935 farmhouse has been updated over the years yet retains its original charm and character. Most recent upgrades within the year include a new kitchen with marble and butcherblock counters, a completely renovated main bathroom, new roof, and more. The grounds are lovely with established perennials, level grassy meadow and woods to the rear. The front entry leads you through a cozy den, which is perfect for a reading or media room, and then beyond to the heart of the home - a bright and sunny open plan kitchen/living/dining area with wood burning stove. The large screened in porch is deliciously inviting for 3 season enjoyment of the backyard and garden views. Additionally on the first floor there is an office, laundry and utility area and full bath. The second story landing is a wonderful surprise. A dormered sitting room with sunlight streaming in serves as another flex space which could be a music room, yoga/exercise room, home office, or art studio. From there the bedrooms and bath branch off in opposite directions creating some buffered privacy between them all. There is an outdoor sauna in the building to the rear and a separate 936 sq. foot 2 car garage that was added in 2018, fully insulated with 200amp service. Possibilities are abundant everywhere on this property for artists, writers, musicians, entrepreneurs, and those seeking a Woodstock lifestyle in a very convenient location. 5 minutes to Woodstock Village, 15 minutes to Kingston. A 3D Walkthrough Tour is available in the digital Lookbook or by request.
Courtesy: Coldwell Banker Village Green
845-679-2255
An opportunity to own a quintessentially Woodstock artist's home, set on half an acre, just moments from the heart of the village. This move-in-ready, character-filled 1920s property offers an appealing balance of original charm, contemporary comfort and exceptional flexibility for work, creativity and everyday living. A covered front porch, approached through colorful garden beds and a stone-paved entry beneath mature trees, creates an inviting sense of arrival. Inside, the generously proportioned living and dining room is warm and atmospheric, with original wood floors, exposed beams and beautifully crafted built-ins, while windows on multiple sides connect the interiors to the garden beyond. A distinctive artist's window adds to the room's character and speaks to the home's creative heritage. The spacious, light-filled, thoughtfully designed kitchen is both stylish and highly functional, with Silestone countertops, a central peninsula with counter seating and thoughtfully integrated appliances including an induction cooktop, wall oven, microwave and French-door refrigerator with dual freezer drawers. Practical conveniences include a workstation sink, glass rinser, dish-drying cabinet above the sink, pot filler and dedicated coffee station. A separate sitting area provides an inviting spot for morning coffee, while a charming Dutch door opens onto a second covered porch and the garden beyond. Upstairs, the exceptionally spacious primary bedroom feels like a private sanctuary. Previously used as the owner's artist's studio, it includes a dedicated sitting area and an impressive north-facing artist's window, adding another layer to the home's creative history. An additional room offers comfortable guest accommodation. The full bathroom pairs warmth and functionality, with a spacious walk-in tiled shower with pebble-stone floor, a vessel sink set on a wood vanity, generous open shelving, and an incorporated washer and dryer. An unfinished attic offers further potential for additional living space, subject to any necessary approvals. The unfinished basement provides additional useful space, with two distinct flexible-use areas currently set up as an artist's workspace and a home office, offering plenty of versatility for creative pursuits, hobbies or projects. A second laundry area with an additional washer and dryer adds further practicality. Outside, the half-acre grounds are an integral part of the property's appeal, with mature trees, established planting around the home and room to further develop the gardens over time. A firepit creates an inviting spot to gather outdoors, while the outdoor shower adds a relaxed, retreat-like quality to the setting. The detached studio offers an inspiring and flexible space for an artist, writer or home office, with vaulted ceilings, exposed beams, a kitchenette and a half bath with cassette toilet. A separate outbuilding provides additional space for a workshop or storage, and there is off-street parking for several cars. Recent improvements include a new roof, mini-split heating and cooling, and a new 200-amp electrical panel, while municipal water and sewer add to the ease of everyday living. Beyond Woodstock's restaurants, cafes, shops, galleries and cultural offerings, the location provides excellent access to the wider Hudson Valley and Catskills, with hiking, swimming, skiing and other outdoor pursuits close by. New York City is just under two hours away. A compelling combination of creative character, outdoor space and convenience, equally well suited to a full-time residence or weekend escape. A 3D Walkthrough Tour is available in the digital Lookbook or by request.
Courtesy: William Pitt Sotheby's
845-677-9822
Where history meets reinvention in Woodstock. From 19th-century barn to 21st-century landmark, come explore one of Woodstock's most extraordinary buildings. With part of the building dating to 1865, this extraordinary 10,000+ square foot barn conversion has been renovated to a high-end standard and is unlike any other structure in Woodstock, and quite possibly unlike any other building in the Catskills. Formerly operated as The Hawthorn, this exceptional building now offers a private residence with a range of possibilities for its next steward. The 6,000 square feet spanning the first and second floors are grandfathered for office, gallery, or studio use, and include a semi-commercial kitchen area, opening the door to a wide variety of live-work or mixed-use configurations. It's an ideal setting for an entrepreneur, artist, or sculptor who needs voluminous, large-scale space to work in, or a musician in search of wide-open acoustics. The possibilities extend further still. Envision a bed and breakfast, a yoga or wellness retreat, an artist's compound, film production or studio, co-working space and professional offices, all within a building that already carries the character and soul these uses thrive on. Exposed posts and beams, bluestone walls, and passive solar south-facing windows speak to the building's history and craftsmanship. The main level with an accessible entrance and bathrooms adds to the building's versatility. A separate one-bedroom apartment with skylights and a private entrance offers additional flexibility for guests, extended family, or rental income. Above it all sits a stunning 3-bedroom, 2-bath penthouse apartment; a genuine retreat within the building itself, complete with a hand-carved sauna, a stone shower, Indian temple doors, stained glass, and a private screened-in porch. Own a piece of history and a piece of now, in one of the most famous small towns in the world. 34 Elwyn Lane is an incredible opportunity in the heart of Woodstock.
Courtesy: Corcoran Country Living
845-338-5832
ROOMS WITH A VIEW! Welcome to 7 Wilber Lane, a stylish mid-century modern ranch set on four glorious acres in the heart of Woodstock, where nearly every room connects you to the beauty outside. Overlook Mountain provides a magnificent backdrop to established gardens, open sky and a wonderfully wild landscape where more than 40 species of birds have been observed. Inside, the home unfolds with an easy, flowing layout filled with light and views. A dramatic living room with beamed cathedral ceilings, hardwood floors and fireplace creates a fabulous central gathering space, opening naturally to the gracious dining area. The home offers three bedrooms, three beautifully renovated full baths, a media room and a private home office with separate entrance—ideal for today's live/work lifestyle. The primary bedroom enjoys its own full bath, while a separate guest en suite opens directly to the backyard, creating wonderful privacy for family and visitors. A galley kitchen with stainless steel appliances and an induction range, two fireplaces, a generous entry foyer and abundant closets add to the home's comfort and character. Thoughtful improvements include Marvin windows, updated kitchen and baths, flooring, electrical and plumbing. An owned solar panel system, privately positioned toward the rear of the property, is another valuable feature and complements the home's connection to its natural setting. And then there is the setting. Step outside to a built-in pool surrounded by nature, mountain views, gardens and four acres of remarkable privacy. This is a property that has been cared for with deep respect for the natural world, where birds, changing seasons and the silhouette of Overlook Mountain become part of everyday life. Tucked away on a quiet dead-end road yet wonderfully close to the heart of Woodstock, 7 Wilber Lane is equally suited to a full-time residence, weekend retreat or inspired live/work escape. Private, peaceful and filled with light—four beautiful acres, a pool, mountain views and rooms with a view. This is Woodstock living.
Courtesy: Coldwell Banker Village Green
845-679-2255
Tucked into the Hillside at Byrdcliffe, halfway up and just below the legendary White Pines of the 300 acre Byrdcliffe sanctuary, is a truly special Woodstock jewel. Hardwood floors flow throughout the easy one-level layout. The spacious living and dining areas fold seamlessly into a generous, bright kitchen, the natural heart of the home. The dining table sits adjacent to a large picture window overlooking the patio. Here all is framed by a mature hedge of green foliage providing both privacy and calm. Sliding doors from the kitchen open to a large screened porch -- perfect for dining, hosting guests, or simply losing an afternoon to a book while the woods do the talking. At the far end of the patio, opposite the porch, a bubbling hot tub awaits. To the rear of the house, on its uphill side, a door from the living room leads to a garden and fenced yard -- currently the happy domain for the owner's puppy. Down the hall from the open living area and the patio front entry are three good-sized bedrooms offering their own quiet privacy. The current owner has combined what was once a fourth bedroom into a generous primary suite. Every bedroom takes in views of the surrounding landscape. This is a home that can be moved into immediately -- and grow into over the years. There's plenty of room for expansion, for gardens, or for carving out a pool sanctuary of your own. An oversized detached two car garage adds even more possibility: a studio, an addition, or simply a great two-car garage. This location is both picturesque and natural. A 3D Walkthrough Tour is available in the digital Lookbook or by request.
Courtesy: Serhant LLC
646-480-7668
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 portion of the house possibly dates to 1875 with various additions added 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 with propane insert, 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 bedrooms share a full bath, while the spacious and grand 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: Compass Greater NY, LLC
914-238-0676
There are places that transcend the idea of home, offering a way of life shaped by beauty, history, and nature. Library Lane Estate, a historically significant property in the heart of Woodstock, is where architectural heritage, artistic provenance, and landscape converge. Nestled along a quiet lane just moments from the village, it offers a rare balance of privacy, connection, and a profound sense of place. Designed and built in the 1920s during the Golden Era of the Woodstock Art Colony by Impressionist painter Paul Arndt, the estate remains a distinguished expression of artistic vision, masterful craftsmanship, and an homage to its heritage. Formally trained at l' École des Beaux-Arts in Paris, Arndt created the Stone House and Studio as his creative sanctuary where he lived and worked for decades. Today, the estate is embraced by gardens envisioned by renowned landscape architect Michael Trapp. Mature trees and layered plantings create a living tapestry evolving throughout the seasons. A vine-covered pergola draped in fragrant honeysuckle reflects the Tuscan countryside and invites a graceful setting for meals and tranquil afternoons beneath the foliage. Library Lane evokes the sensibility of a Europnean country estate and the timeless character of the Cotswolds interpreted through the artistic spirit of Woodstock. Here, slow living becomes a natural rhythm. The Stone House has been restored with deep respect for its original character. Hand-trowelled plaster walls, exposed beams, original wide-plank floors, and interior stone walls provide both texture and a sense of enduring sophistication and repose. The subtle lighting brings forth details and creates an ambiance of sacred space. The French casement windows welcome light, soft breezes, aromas, and birdsong, while beyond the wavy glass rests the century-old willow. A stately stone-clad wood-burning fireplace anchors the generous living room becoming the heart of the home. The bespoke kitchen, designed with Siberian elm countertops, Clé tile, and an unlacquered-brass Barber Wilson faucet flows into the exquisite sunlit dining room. Beyond the meandering gardens and through the hidden gate, stands the reimagined Arndt studio. The three-bedroom Cottage carries a luminosity and the proportions of its original intention. Vaulted ceilings rise above an original stone fireplace fitted with a Stûv Belgian insert, while wide pine floors, reclaimed barnwood cabinetry, skylights, and a screened porch create a restful haven. Each comfortable bedroom and bath is a sunlit pleasure. A Venetian-plastered bath created by artist Anthony Chase provides an artisanal finish deepening the connection between material, light, and craft. A true Woodstock landmark, this exceptional estate offers the rare opportunity to become stewards of a property where history, artistry, and nature remain beautifully intertwined. The Stone House and Cottage each occupy their own parcel and private grounds. Far more than an estate, this is a collectible cultural legacy.
Courtesy: Compass Greater NY, LLC
845-334-0227
Few properties embody the history, architecture, and landscape of Woodstock as completely as the Lewis House. On the side of Overlook Mountain, at the very top of Lewis Hollow Road, and surrounded by thousands of acres of protected forest on Overlook Mountain, this remarkable property has evolved over more than 220 years while retaining the quiet character that makes it truly timeless. The original quarry house, dating to 1805, forms the heart of the current home, with what are now the living room and library serving as its earliest rooms and bedrooms above. Successive stewards thoughtfully expanded the residence rather than reinventing it, allowing each generation to contribute its own chapter. A striking addition completed in the 1960s introduced tall, gently curving windows overlooking the mountain stream, filling the home with natural light and creating a constant connection to the sound and movement of water. In the 1980s, the current owners added a spacious kitchen with soaring ceilings centered around an antique Queen Atlantic wood-burning cooking stove and oven, although one usually uses the Garland gas range and wall oven. Also added was a garage which can transform into a summer kitchen and entertainment area. Above that is a studio that has its own private entrance and patio, kitchenette and full bath--equally suited for guests, creative work, or a future primary suite. The home's history is woven into the cultural fabric of Woodstock. During the 1940s and 1950s it was home to historian and author Alf Evers, whose entertaining and well researched books on the Catskills, Woodstock and Kingston remain the definitive histories of the area. The white wisteria that still graces the front of the home recalls the annual Evers Wisteria Party, a reminder that this house has long been a place where people gathered to appreciate the beauty of its surroundings. Later featured in ''Good Housekeeping,'' whose editor headlined it as ''The Perfect Country Home.'' Outside, the landscape is every bit as compelling as the home itself. Ancient stone walls define open lawns, mature trees, flowering gardens, woodlands and meadows that were formerly apple orchards, while the mountain stream and waterfalls wind through the property beside the house. The in-ground pool, framed by local blue-stone, feels as though it has always belonged here. A wood shed and charming outbuilding add both function and character, while the hillside above reveals sweeping views across the Hudson Valley toward Kingston, with Overlook Mountain rising dramatically in the opposite direction. It is rare to find such complete privacy while remaining only three miles from the heart of Woodstock. The home offers remarkable flexibility, with three bedrooms and a full bath on the second floor, additional guest accommodations on the main level, and the studio providing either independent living quarters or a seamless extension of the home. Two fireplaces continue to anchor during the colder months, while a newer roof, standby generator, walkout basement with mechanical systems, and thoughtfully maintained pool equipment provide comfort and peace of mind throughout the seasons. More than a historic home, the Lewis House is a landscape, a retreat, and a piece of Woodstock's enduring story. It is a place where handsome architecture and beautiful landscaping have evolved with care over generations, where the sound of the stream becomes part of daily life, and where the next owner has the rare opportunity to become the steward of one of Woodstock's most distinctive properties.
Courtesy: Halter Associates Realty
845-679-2010
Woodstock Charm, Mid-Century Style & Garden-Lover's Paradise just minutes from the heart of Woodstock, this sweet, well-maintained mid-century modern ranch offers the perfect blend of character, comfort, and convenience. Set on nearly an acre, the property provides a peaceful retreat while keeping you close to everything that makes Woodstock so special--eclectic shops, acclaimed restaurants, theaters, golf, and the vibrant village atmosphere. Inside, cathedral ceilings with exposed beams create a warm, open feel, while the updated kitchen flows seamlessly into the living space. A beautiful brick fireplace with an insert adds a cozy focal point for relaxing year-round. The full, unfinished basement provides a laundry area and includes a Britt & Graff oil tank. Outside, the nearly one-acre property is a gardener's delight, with an abundance of established plants and inviting garden spaces to enjoy. Whether you're searching for a full-time residence or a special weekend getaway, this Woodstock property is well worth a look. A wonderful opportunity to own a piece of the Woodstock lifestyle in a prime location. New roof 2016, furnace 2011, oil tank 2024, well head 2025, garage door 2014.
Courtesy: Coldwell Banker Village Green
845-679-2255
With nearly 14 acres, a heated saltwater pool, a separate two-bedroom ADU, and a warm character-filled main house, this Woodstock stream side country compound has been reimagined and meticulously updated within the last 5 years from soup to nuts. It is move-in ready as a weekend home, Air B&B or full-time residence. The main residence has the relaxed unpretentious character that makes a house feel immediately like home. Sun filled rooms, exposed beams, wood floors The beautifully appointed kitchen with Sub-Zero fridge, Bertazzoni range, extra thick quartz countertops and plenty of cabinetry is truly a cook's haven. Don't miss the sweet 3 season sunroom - a great spot for reading or meditating, and the mudroom off the kitchen to store boots and other outdoor paraphernalia. All 3 baths have been updated as well as all major systems in the home. A 1st floor bedroom plus 2 bedrooms and a den upstairs offer plenty of sleeping space for everyone and the super large primary suite w/balcony overlooking the pool, stream, gardens and woods beyond. The basement is partially finished, great for workshop, rec room and storage galore. A wrap around deck and covered front porch provide endless enjoyment in warmer weather. The 2 bedroom ADU/rental above the garage for guests, Air B&B or full time rental income includes a large living/work space on the lower level suitable for yoga, gym or an art studio For nature lovers there are 13+ private acres to enjoy gardening, hiking, badminton, or lazing in a hammock. A beautiful fenced in perennial garden has the most adorable shed painted in whimsical colors and is perfect as a playhouse, artist's studio, or summer glamping spot. This is a great property for those seeking a Catskills country lifestyle with acreage, but only minutes to the Villages of Woodstock or Saugerties. Enjoy a Woodstock mailing address with Saugerties STR permit availability. Sellers previously operated a profitable Air B&B with Super Host status. All the mechanicals in the home have been replaced or upgraded. The HVAC was replaced including a new boiler and radiant heat added on the 1st floor, 2 new heat pumps, 2 new air handlers. Additional panels were added to the existing solar array, amping it to 27 panels plus a new inverter and 17KW battery backup for power outages. Exterior stained and painted. A 3D Walkthrough Tour is available in the digital Lookbook or by request.
Courtesy: Brown Harris Stevens Hudson
518-828-0181
A STORYBOOK WOODSTOCK RETREAT IN THE WOODS Some homes provide shelter; others provide sanctuary. 357 Chestnut Hill Road is a sanctuary in the woods--a soulful Woodstock retreat where sunlight spills through skylights, pine glows underfoot, and the forest seems to lean in and whisper, ''stay awhile.'' Set on 1.6 wooded acres with approximately 257 feet of road frontage, this enchanting red-clad hideaway has been treasured by one close family since 1970. Follow the gravel drive beneath a leafy canopy and the home gradually reveals itself among the trees, its warm wood exterior appearing almost organically from the landscape. Secluded without feeling isolated, it captures the creative, carefree spirit that has long made Woodstock irresistible. Inside, 1,338 square feet includes a primary bedroom, a bath, a kitchen, a wonderfully versatile loft, and the home's showpiece: a spacious, cozy living room where an exposed beamed-wood ceiling creates an architectural rhythm overhead, while skylights pour pools of daylight across pine floors below. Windows frame the surrounding woodland. A characterful brick fireplace anchors it all. On crisp Catskills evenings, the hearth becomes the heart of the house--a natural gathering place for conversation, contemplation, and fireside nights. Rustic textures, warm woods, and natural light lend the room an atmosphere at once dramatic and deeply comfortable. The adjoining kitchen and dining area anchor the country cabin's soul with wood cabinetry, exposed beams, a vaulted ceiling, and an overhead skylight. Equipped with a refrigerator, range/oven, dishwasher, and washer/dryer, it is an inviting, unpretentious space for everything from pancakes at sunrise to pasta and pinot after a day exploring. And then there is the porch! Wrapping around two sides of the kitchen, the sprawling screened porch creates an irresistible indoor-outdoor area suspended within the trees. Here, the forest becomes the wallpaper and birdsong the soundtrack. Rain can patter overhead, leaves can rustle beyond the screens, and summer evenings can linger long after the sun disappears. The upper loft adds an unexpected dimension to the home's mostly single-level layout. Wrapped in warm wood, this flexible aerie can readily accommodate an additional sleeping space and a home office, library, studio, meditation area, or creative escape. Space creates possibility, and possibility gives a home room to evolve. Four split-system units add modern comfort, while a 260-square-foot partial basement provides additional utility. The house's roof was replaced in 2020. Outside, the property becomes a private woodland world. Mature trees tower overhead, sunlight dapples the forest floor, and the home's distinctive red exterior provides a warm counterpoint to the seemingly endless green. The gently winding gravel drive continues uphill to a particularly valuable feature: an oversized detached garage. With its dedicated entrance, windows, and loft storage above, the garage offers far more than parking. Think workshop, equipment storage, hobby headquarters, or simply the rare luxury of having room for all the things that make country life more enjoyable. Its roof was replaced in 2023. Yet the real luxury here cannot be quantified by acreage or square footage. It is privacy, peace, and place. For more than half a century, one family has returned to this home, lovingly cared for it, gathered within it, and called it their retreat. That continuity gives 357 Chestnut Hill Road something no renovation can manufacture: soul. The house does not ask to be something it isn't; its weathered woods, exposed beams, skylights, fireplace, loft, porch, and forest setting tell an authentic story of Woodstock country living--and invite a new owner to write its next chapter. Retreat becomes refuge; refuge becomes home; and every great story needs a place to begin--make 357 Chestnut Hill Road the beginning of yours.
Courtesy: BHHS HUDSON VALLEY PROP-WDST
845-679-0006
Originally built by the developer of Simmons Drive as his personal home, this spacious Woodstock property offers a rare combination of Village convenience, mountain views, and a peaceful park-like setting. Situated on a quiet no-outlet street, it's just a five-minute stroll to Good Night restaurant, Tinker Street shopping, cafés, galleries, and everything the Village of Woodstock has to offer, all while enjoying a backyard shaded by mature trees and bordering Andy Lee Field, with no residential neighbors directly behind you. The home offers three bedrooms, though it lives comfortably as four, with plenty of additional flexible space. An enclosed porch and wood-burning stove add warmth and character, while skylights bring natural light into the sunroom. Opening directly onto the deck, the sunroom offers an exciting opportunity to create a generous primary suite. Downstairs, an additional flex room can serve as an office, exercise room, creative space, or extra storage. A two-car garage provides even more room for storage and projects, while the backyard offers space to gather around the fire pit beneath the trees. Lovingly maintained and improved over the years, the home has seen numerous important updates, including bathrooms updated in 2019, a 200-amp electrical service, a furnace rebuilt in 2025, an approximately five-year-old oil tank, a main roof approximately nine years old, and fencing and decking improvements completed in 2019. Big enough for all your friends, flexible enough for the way you actually want to live, and just minutes from the heart of Woodstock by any means of travel.
Courtesy: Halter Associates Realty Inc
845-679-2010
In the heart of Woodstock Village, this beautifully reimagined Colonial offers the rare combination of historic character, modern comfort, and true **walk anywhere convenience**. Set beside Tannery Brook, the home is designed to make the most of its stream side setting, with light-filled interiors, an open-concept layout, and two sets of French doors that create an effortless connection to the outdoors. A newly built 300-square-foot deck overlooks the water and provides an exceptional space for dining, entertaining, or simply relaxing to the sound of the brook. An outdoor shower adds to the relaxed country feel, while the home’s village location keeps restaurants, shops, galleries, cafés, and music just minutes away. Inside, the great room is warm and inviting, with a wood stove for cozy evenings, solid wood flooring and elegant finishes throughout. The kitchen features Carrera marble counters and detailing, while the flexible stream-facing studio space is perfect for entertaining, creative use, or a ground-floor office. The home has been thoughtfully updated with new Andersen windows, mini-splits, and upgraded 200-amp electric service. The bathrooms blend luxury and craftsmanship, including double shower heads in the main bath and a custom vanity made from beams reclaimed from the original structure. Upstairs, the romantic primary bedroom features a clawfoot tub and an oversized walk-in closet. This is Woodstock living at its best: restored, stylish, comfortable, and surrounded by natural beauty, with every village convenience just outside your door.
Courtesy: Ruth Gale Realty
845-688-5610
Family Compound and/or Investment Property. There are 3 homes at 5 & 7 Parker Lane in Woodstock. The property is located only minutes from Main St in Woodstock. The 5 Parker Ln cottage has 1423 square feet with 2 bedrooms & 1 bathroom. 7 Parker Ln has 2 homes on the lot. The 2-story home has 1231 square feet with 2 bedrooms & 1.5 bathrooms. The cabin at 7 Parker Ln has 1 bedroom & 1 bathroom. For this listing, I combined both 5 & 7 Parker Ln school tax, general tax, square footage, number of bedrooms, bathrooms and acreage. I can provide the separate details. When you are at the compound, there is a wonderful sense of privacy. There is a little pond behind the property that is shared with the neighbors. This is an incredible opportunity to own a family compound and investment property in the heart of Woodstock.
Courtesy: Four Seasons Sotheby's Int'l R
845-684-0084
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 relaxing under the stars. The detached garage with ample storage includes a finished, insulated room, perfect for a home office, art studio, or creative workspace. Located just a short stroll from Woodstock's vibrant village, acclaimed restaurants, theater, health food store, and the popular Bearsville Complex, you'll have the best of the Catskills right at your doorstep. Whether you're starting your homeownership journey, looking to downsize, or searching for a smart investment, this Woodstock gem has it all. Move right in and make it yours!
Courtesy: KW Hudson Valley North
845-481-2700
Welcome to The Waterfall House, a rare opportunity tucked away in the heart of Woodstock Proper. Set on nearly 12 private acres, this classic brick Colonial offers an exceptional combination of privacy, natural beauty, and endless potential, all just minutes from the shops, restaurants, galleries, and vibrant arts scene that have made Woodstock an iconic destination. Offering approximately 3,000 square feet, the home features six legal bedrooms and 3.5 baths, with expansive living spaces ready for your personal vision. Whether imagined as a full-time residence or a weekend escape, this is a property with room to gather, unwind, and make your own. The true centerpiece is the spectacular rear sunroom, where walls of windows frame the surrounding forest and invite the outdoors in. Open the windows and let the soothing sounds of your private waterfall and babbling brook become the soundtrack to everyday life, creating a setting that feels peaceful, restorative, and far removed from the everyday. Outside, nearly 12 acres of mature woodland offer room to explore, exceptional privacy, and an immersive connection to nature that is increasingly difficult to find. Tucked quietly along the water's edge are two charming artist cabins, a subtle reminder of the property's history and the artistic spirit that has long been woven into Woodstock's identity. Their presence adds another layer of character to an already unforgettable landscape. Properties like this rarely become available. Blending an extraordinary natural setting with the timeless character and spirit of Woodstock, The Waterfall House is one of the Hudson Valley's most distinctive offerings, ready for its next chapter.
Courtesy: William Pitt Sothebys Int Rlty
845-677-5512
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 overlooks the gunite pool, while a separate studio building introduces endless possibilities: artist studio, guest overflow, workspace, movement room, or retreat space. At the edge of the property sits a whimsical treehouse tucked into the woods, adding yet another layer to the property's distinctly Woodstock character. Longtime home to Woodstock artist Lenny Kislin, the property carries a deeply creative spirit shaped over decades. An acclaimed assemblage artist, Kislin created witty and deeply poignant sculptures by bringing together carefully sourced antique components and found objects, transforming fragments of the past into works rich with meaning and imagination. His work remains integrated throughout the home and studio. Private, architectural, and rich with atmosphere, 41 Wittenberg is a rare offering. This property has genuine soul, minutes from the center of Woodstock yet entirely its own world.
Courtesy: Coldwell Banker Village Green
845-679-2255
Set on an almost 3-acre wooded lot, this property has so much to offer in a quiet location close to the Village Green. On the main floor, you have a choice of rooms in which to entertain. A generous foyer leads to a comfortable living room with an actual dining room opposite. Beyond that space, a bright, recently redone, cheery eat-in kitchen awaits. Down the hall, for those cozy nights, a brick-fireplaced den opens to a double French-doored breezeway. Along the hall is a convenient half bath and laundry room, too. A series of doors and a delightful screen porch all overlook the pool area, awaiting your summer fun. The upper level contains 3 spacious bedrooms with generous closets, which share a large bath. The primary ensuite, with walk-in closets, completes this floor. The natural setting around the sparkling pool adds to your private relaxation. Please come see for yourself... A 3D Walkthrough Tour is available in the digital Lookbook or by request.
Courtesy: Taft Street Realty, Inc.
845-687-9292
Rarely does a Woodstock home come along with this much soul, flexibility, and built-in opportunity. Tucked away on just over an acre off private Chipmunk Lane, this charming 2265 sq ft Cape Cod cottage style home captures the feeling people come to Woodstock hoping to find: a little privacy, a little magic, a little room to create, and a home that feels deeply personal from the moment you arrive. At the heart of the main house is a wonderfully memorable kitchen, full of color, character, and warmth. This is not a showroom kitchen trying too hard. It is the kind of kitchen where meals stretch into stories, friends gather around the island, coffee starts slowly, and the house begins to feel like home. The adjoining living areas continue that same spirit, offering inviting spaces for conversation, quiet mornings, winter nights in front of the wood stove, and the everyday rhythm of country life. The main home offers two bedrooms and two full baths, along with a highly useful first-floor office/flex room off the living room that can easily function as a guest room, studio, work-from-home space, or possible first-floor sleeping area. Upstairs, vaulted ceilings and exposed beams bring classic Cape Cod charm to a second living area that could become a media room, playroom, creative workspace, or future bedroom or bath, depending on your needs. What makes this property especially rare is the legal, fully licensed short-term rental component. Connected through the center mudroom yet able to live entirely separately, the one-bedroom guest suite creates meaningful income potential without compromising the privacy or normal function of the main home. With its own entrance, separate driveway, private parking, and established Airbnb history, it feels less like an afterthought and more like a thoughtful second world on the property. For artists, makers, musicians, remote workers, weekenders, or anyone looking for a Woodstock home that can support both lifestyle and income, the versatility here is exceptional. Live in the main house and rent the guest suite. Keep the suite for visiting friends and family. Use it as a detached-feeling studio, wellness space, or creative retreat. The layout gives you options now and flexibility for whatever comes next. The setting is equally compelling. Over an acre gives the property breathing room, with mature trees, garden moments, and a tucked-away feeling that still keeps you close to the village proper of Woodstock. Historic Kingston, Saugerties, hiking, restaurants, music, shops, and farm-to-table favorites are all within easy reach, and the Kingston Thruway exit is less than 10 minutes away for a more convenient connection back to New York City. This is the rare Woodstock combination buyers keep hoping to find but almost never do: character, privacy, legal short-term rental income, separate living spaces, creative flexibility, and a location that feels both hidden away and connected to everything. A cottage home with charm, a property with purpose, and a lifestyle that is ready to begin on day one.
Courtesy: Coldwell Banker Village Green
845-679-2255
Nestled in a quiet Woodstock neighborhood five minutes from the village center and a short drive from Kingston, The Van Dale offers the privacy of nature without sacrificing convenience. Set on 1.36 acres in a quiet neighborhood, the property is bordered by a private creek that winds through the backyard, creating a peaceful natural setting just minutes from some of the Hudson Valley's most vibrant destinations. Spanning nearly 2,000 square feet, this three-bedroom, three-bath home is thoughtfully designed for comfortable full-time living or weekend escapes. The open living room is anchored by a floor-to-ceiling bluestone fireplace with an efficient wood stove insert, while walls of windows fill the space with natural light and frame views of the surrounding pines and front gardens. Hardwood floors run throughout the main living areas and bedrooms, adding warmth and continuity. The bright and welcoming kitchen features custom cabinetry and a generous butcher block center island, creating a space equally suited for everyday living and entertaining. Just beyond, the dining area flows to a beautiful screened porch overlooking the backyard, woods, and creek. A newly refurbished deck extends the outdoor living space, while a fire pit and play area invite long afternoons and evenings spent outdoors. All three bedrooms and two updated bathrooms are conveniently located on the main level. The primary suite offers a walk-in closet and a spacious en-suite bath illuminated by a skylight, creating a bright and relaxing space. A thoughtfully positioned laundry area nearby adds ease to daily living. The lower level offers exceptional flexibility, with a spacious family room that runs the length of the home. A second fireplace with a wood insert creates a cozy atmosphere, while doors open to a sunny mudroom and the expansive backyard beyond. This level also includes a full bathroom, kitchenette, and direct access to the attached two-car garage, making it ideal for guests, recreation, or extended living arrangements. Hiking, skiing, swimming, golf, and tennis are all within easy reach. So is Woodstock itself: live music, great restaurants, galleries, and a cultural energy no other Hudson Valley town quite replicates. Available fully furnished, with inventories of furnishings and recent improvements upon request. A 3D Walkthrough Tour is also available in the digital Lookbook or by request.
Woodstock is located in New York. Woodstock, New York 12498has a population of 6,215. Woodstock 12498 is less family-centric than the surrounding county with 17.98% 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 12498 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 12498 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.
