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: 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 bordering vast 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: BHHS Hudson Valley Properties
845-679-0006
Wend up a pristine country road to this 2,300 sq ft Woodstock contemporary—arriving to total seclusion and picturesque views, yet only minutes to the Village Green. This domain is set on 4+ private acres with an additional almost 4 acre, separately-deeded, contiguous parcel that makes it an ideal property for a compound, or to use with it's maximum natural buffer for ultimate privacy. Close proximity to State land and trails from your own private road further adds to the splendor of the premises. Step into an open, flowing layout connecting the stunning, sleek and seductive kitchen with the dining and living areas. The kitchen provides easy access to an outdoor herb garden and BBQ space out back. All this is married together by vaulted and beamed ceilings, expansive windows throughout, and doors out of every first-level room—seamlessly connecting indoor spaces with outdoor living and creating a truly natural retreat. The living room basks in sunlight and boasts walls of windows and skylights, and flows out to a peaceful deck overlooking "those famous Catskill Mountain views". Although the town shows this home to be two-bedrooms, the current owner is using a first floor den as an additional guest-sleeping-area. This room is joined to the main living space through a charming office/sitting area, and is surrounded by glass sliding doors with walkways to the lovely outdoors. Cozy up to a massive wood stove after enjoying outdoor activities, or just to read a novel on cold winter nights. Upstairs, you’re greeted by an open loge that leads to two large bedrooms—including a primary with a NYC loft-like feel—and a luxurious shared bath. Wood floors and rich natural details add warmth and character throughout the house. Multiple decks and walkways lead to the surrounding grounds that feature a broad landscaped lawn, a fern meadow, forest, gardens with perennial plantings, and a small fruit tree orchard—perfect for outdoor enjoyment and entertaining for everyone. Dine al fresco just outside the kitchen, host gatherings, or simply relax in this tranquil setting. Electric service to the property is underground so there are no ungainly wires cluttering your views. Energy-efficient systems include: a massive rooftop solar array with backup battery, geothermal wells, and an electric car charging station that provide near off-the-grid living with minimal utility bills. All this, just minutes from Woodstock's curated shops, chef-owned restaurants, cultural attractions and recreational options, and live music events at the Bearsville Theatre. Enjoy Belleayre or Hunter Mountain and all the Catskills have to offer. A rare offering combining privacy, sustainability, and style. A pleasure to see and show!
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: Coldwell Banker Village Green
845-679-2255
Perfectly situated just minutes from the vibrant village of Woodstock, while equally convenient to Kingston and Saugerties, this immaculate and thoughtfully updated home offers the best of Catskills living in a truly welcoming neighborhood setting. Lovingly maintained and completely turnkey, the residence exudes warmth and understated elegance throughout. The entry level features a spacious den with sliding glass doors that open to a serene backyard where nature takes center stage--frequent visits from deer and local wildlife enhance the peaceful, country ambiance. The neighborhood itself invites an easy, leisurely lifestyle, ideal for morning strolls, walking dogs, bike rides, or a short drive into town for exquisite fine dining, shopping, and galleries. Just above the den and laundry area, the large, well-appointed living room is anchored by a striking stone fireplace with a beautiful hearth, while a large bay picture window fills the space with natural light. The spacious living room area flows seamlessly into the eat-in kitchen and adjoining dining area, where additional sliders lead to an elevated rear deck overlooking the beautiful, wooded property--perfect for entertaining or quiet evenings outdoors. Three bedrooms complete the home, including a comfortable primary suite with its own bath, along with a guest bedroom conveniently located across from a second full bath. With a nice sized laundry room, two full bathrooms, a versatile den, basement and a two-car garage, this refined yet inviting home offers a perfect blend of sophistication, space, privacy, comfort, and effortless Catskills charm--an ideal retreat for gathering with loved ones and creating lasting memories. A 3D Walkthrough Tour is available in the digital Lookbook or by request.
Courtesy: Coldwell Banker Village Green
845-679-2255
Some properties are about the house - this one begins with the water. Sit by the year-round creek for a few minutes and everything slows; it's a setting that quietly draws you in and holds you there. Set on two wooded acres along the Sawkill Creek, and tucked away at the end of long driveway just minutes from the center of Woodstock, the house is positioned to take full advantage of its surroundings - with views to the water from the great room, the expansive rear deck and the upstairs loft. In the warmer months, the creek becomes part of daily life, offering a place to cool down, unwind, or simply sit and take it in, with two swimming holes, including the Big Deep, just moments away. The grounds have been carefully and thoughtfully shaped to complement the setting, with layers of seasonal interest throughout the year - rhododendrons blooming along the upper bank of the creek in spring, a magnolia in soft pink just off the house, and a striking ginkgo that turns a luminous yellow in autumn. Wildflower meadows, ornamental grasses, and perennial herbs bring a more relaxed, natural feel to the landscape, creating a setting that feels both intentional and effortlessly in tune with its surroundings. Inside, the light-filled main living space opens beneath soaring vaulted ceilings, where a stacked stone fireplace serves as the focal point of the room - bringing warmth, texture, and a sense of scale to the otherwise clean, wood-lined interior. Two sets of sliding doors open out to the deck, creating a natural connection to the outdoors; in the warmer months, they can be left open to let in the sound of the creek, so the setting becomes part of the room itself. The great room flows easily into a defined dining area, positioned to take in the same views and connection to the landscape, and continues through to the kitchen, where generous cabinetry, a central island, and ample workspace support both everyday living and entertaining. The layout includes three spacious bedrooms and three full bathrooms, including a primary suite with a spacious, spa-like bath featuring a freestanding soaking tub and separate shower. A guest bedroom on the main level, with its own full bath, offers privacy and comfort for visitors. A practical laundry room provides a natural transition from the outdoors - particularly after a dip in the creek - supporting easy, everyday living, and rounding out the main level. Upstairs, a second living area overlooks the main space below, maintaining a visual connection to the great room while creating an airy retreat that works equally well for reading, quiet time, or work. This upper level also includes a third bedroom and third full bath, along with an additional finished room that offers flexibility for a home office, studio, or overflow space for guests. Newly built in 2024 and elevated above the floodplain, the home is connected to the town sewer, and offers the ease of new construction with a strong connection to its setting. Additional features include an oversized, attached two-car garage and efficient systems throughout. Woodstock remains one of the Hudson Valley's most sought-after destinations - known for its unique shops, eclectic dining, and vibrant cultural scene - while also offering easy access to hiking, swimming, and skiing throughout the Catskills. From here, you're just under two hours from New York City, making this an easy weekend escape or full-time base with a strong connection to both nature and community. A 3D Walkthrough Tour is available in the digital Lookbook or by request.
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: Coldwell Banker Village Green
845-679-2255
Some properties are about the house - this one begins with the water. Sit by the year-round creek for a few minutes and everything slows; it's a setting that quietly draws you in and holds you there. Set on two wooded acres along the Sawkill Creek, and tucked away at the end of long driveway just minutes from the center of Woodstock, the house is positioned to take full advantage of its surroundings - with views to the water from the great room, the expansive rear deck and the upstairs loft. In the warmer months, the creek becomes part of daily life, offering a place to cool down, unwind, or simply sit and take it in, with two swimming holes, including the Big Deep, just moments away. The grounds have been carefully and thoughtfully shaped to complement the setting, with layers of seasonal interest throughout the year - rhododendrons blooming along the upper bank of the creek in spring, a magnolia in soft pink just off the house, and a striking ginkgo that turns a luminous yellow in autumn. Wildflower meadows, ornamental grasses, and perennial herbs bring a more relaxed, natural feel to the landscape, creating a setting that feels both intentional and effortlessly in tune with its surroundings. Inside, the light-filled main living space opens beneath soaring vaulted ceilings, where a stacked stone fireplace serves as the focal point of the room - bringing warmth, texture, and a sense of scale to the otherwise clean, wood-lined interior. Two sets of sliding doors open out to the deck, creating a natural connection to the outdoors; in the warmer months, they can be left open to let in the sound of the creek, so the setting becomes part of the room itself. The great room flows easily into a defined dining area, positioned to take in the same views and connection to the landscape, and continues through to the kitchen, where generous cabinetry, a central island, and ample workspace support both everyday living and entertaining. The layout includes three spacious bedrooms and three full bathrooms, including a primary suite with a spacious, spa-like bath featuring a freestanding soaking tub and separate shower. A guest bedroom on the main level, with its own full bath, offers privacy and comfort for visitors. A practical laundry room provides a natural transition from the outdoors - particularly after a dip in the creek - supporting easy, everyday living, and rounding out the main level. Upstairs, a second living area overlooks the main space below, maintaining a visual connection to the great room while creating an airy retreat that works equally well for reading, quiet time, or work. This upper level also includes a third bedroom and third full bath, along with an additional finished room that offers flexibility for a home office, studio, or overflow space for guests. Newly built in 2024 and elevated above the floodplain, the home is connected to the town sewer, and offers the ease of new construction with a strong connection to its setting. Additional features include an oversized, attached two-car garage and efficient systems throughout. Woodstock remains one of the Hudson Valley's most sought-after destinations - known for its unique shops, eclectic dining, and vibrant cultural scene - while also offering easy access to hiking, swimming, and skiing throughout the Catskills. From here, you're just under two hours from New York City, making this an easy weekend escape or full-time base with a strong connection to both nature and community. A 3D Walkthrough Tour is available in the digital Lookbook or by request.
Courtesy: Compass Greater New York, 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.
Welcome to Bearsville Record House, a landmark property with a legacy in American music. Built in 1873 and once home to Bearsville Records, this storied compound includes two dwellings; the main farmhouse and a guest cottage, plus a studio building waiting to be finished to your specs. A gunite saltwater pool, outdoor kitchen, and fenced-in plum orchard complete the grounds, all along 500 feet of private Sawkill creek frontage. The main house retains its 19th-century character with a vaulted living room with wood stove, library with cedar sauna, and a chef's kitchen with dramatic wood-burning hearth and radiant-heated bluestone floors. The guest cottage features a walk-in shower and kitchenette, and the studio adds creative flexibility. Steps from Cub Market and Bearsville Theater, and just two miles from Woodstock, this is a one-of-a-kind Catskills cultural retreat.
Courtesy: William Pitt Sothebys Int Rlty
845-677-9822
Enchanting Woodstock Compound with a Craftsman Home, Cottage, and Historic Barn. Welcome to a truly rare offering in the heart of the Catskills, just minutes from the center of Woodstock, yet tucked away in a storybook setting of trees, meadows, and the soothing sounds of the Sawkill stream. This private 1.85-acre homestead compound blends rustic charm with modern versatility, featuring a Craftsman home, sun-drenched cottage, and historic barn. Each building has its own character, purpose, and potential. The Craftsman Home. Thoughtfully restored and offered fully furnished, this two-story residence boasts cozy elegance and charm. An inviting front porch sets the tone for relaxed country living, while the 3-season sunroom offers the perfect perch for morning coffee or quiet reading. Inside, original hardwood floors, wainscoted ceilings, and a bright, open layout offer space for entertainment and relaxation. Upstairs, two bedrooms and a stylish bath provide a peaceful retreat. The spacious basement offers extra storage or workshop potential. Currently operating as a short-term rental, this home is truly turn-key for those seeking an income-producing property or an effortless weekend escape. The Bearsville Cottage. A charming blend of vintage soul and creative flair, this one story, two-bedroom, one bath cottage is perfect as a guest house, rental unit, or home office. Exposed wood beams, oversized artist windows, and a cozy woodstove make the living space both inspiring and inviting. A private bedroom entrance offers added privacy for tenants or guests, while the open kitchen and living area seamlessly extends into the backyard for easy indoor-outdoor living. The Historic Barn. Once home to the Bearsville Woodworking Collective, where the famed Pete Seeger commissioned the building of the Hudson River Sloop, Woody Guthrie, this large barn holds a legacy of artistry and craftsmanship. Its soaring ceilings, open floor plan, and natural light make it ideal for a studio, gallery, or workshop. French doors open to a bluestone patio overlooking stone gardens and field, an inspiring space for creatives or gatherings. The upper attic provides additional space for storage or future expansion. The Land & Location. The Woodstock compound is fully fenced with fruit trees, open field, and garden beds; ideal for farming or simply enjoying quiet nights under the stars. A babbling creek runs year-round, adding to the property's natural serenity. Whether you're dreaming of a regenerative homestead, a live/work artist's retreat, a multi-generational family property, or an income-generating opportunity; this magical compound offers flexibility and soul in equal measure. Located just minutes from Woodstock's vibrant restaurants, music venues including the Bearsville Theater, and art galleries with easy access to hiking, swimming, and all the natural beauty of the Catskills. This is a truly one-of-a-kind offering where history, nature, and creative potential come together.
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.
Courtesy: Frank Lumia Real Estate Plus!, LLC
607-746-6029
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: BHHS HUDSON VALLEY PROP-WDST
845-679-0006
BACK ON THE MARKET! BUYER FINANCING FELL THROUGH All the charm and convenience of Woodstock village living! Adorable period bungalow moments from the center of Woodstock! This 1 BR, 1 BA charmer features an additional room/four-season sunroom, handsome masonry fireplace with wood stove and a river rock chimney, modern kitchen, a clawfoot tub, separate laundry area, and is nestled in a wooded, nearly quarter-acre lot with a sunny lawn. Plus a BRAND NEW HEATING SYSTEM has just been installed! An 8x12 storage shed is great for bikes, tools, etc. Perfect as a starter home, weekend getaway or investment property. Moments to all the dining, entertainment, shops, hiking, biking and golfing that Woodstock has to offer. Make this your base to enjoy the skiing, hiking, swimming and wonderful energy of the Catskills, with your very own piece of the Woodstock state of mind.
Courtesy: Compass Greater NY, LLC
914-238-0676
PROPERTY HIGHLIGHTS. Big ''Tiny House'': Designed for people who love Small Efficient Spaces, by the Water, with Mountain Views, enjoy living ''uncarred'', in the most Central Location in Woodstock. Layout: 2 bedrooms and 2 bathrooms. Exceptionally rare Climate Resilient Construction featuring Steel floor and ceiling joists with comprehensive Energy Efficient Upgrades throughout. INTERIOR FEATURES KITCHEN: Energy Efficient and dependable Bosch appliances. Custom Transformad Cabinetry with high-tech, anti-fingerprint, impact and scratch-resistant, auto-regenerative, super matte lacquered finish. Custom made solid Walnut and Steel open shelving, plus a high-gloss lacquered Pantry for both function and beauty, and quartz countertops. BATHROOMS: Floor to Ceiling imported tiles, artisan-quality installations Kohler Purist fixtures, and Cedar plank ceilings. Kohler Purist fixtures, and Cedar plank ceilings. FLOORING: Reclaimed Oak Floors from the original structure upstairs. New Oak Floors downstairs. LIGHTING AND FIREPLACE: Elegant Le Feu Bioethanol Fireplace for warmth and ambiance. Thoughtfully sourced Vintage and Modern Lighting fixtures throughout. COMFORT AND EFFICIENCY. Steel floor and ceiling joists for the ultimate in structural integrity. Spray-foam and mineral wool insulation throughout. All-new Plumbing and Electrical systems. Energy-efficient Mitsubishi heat pump providing central air and heat. Asko Washer and Dryer, Pella windows and doors. Clean Space System installed in the crawl space for added protection and peace of mind. OUTDOOR FEATURES. New screened-in porch with Bronze screens, exquisite carpentry, and elegant French doors. New bluestone and brick walkway. Fully restored garage with new roof system while retaining its original details and preserving its historic character. LOCATION AND SETTING. The most central location in Woodstock, with easy access to the bus to NYC. Beautiful stream (the west branch of Tannery Brook) runs through the property. Mountain views and a serene natural backdrop. Enjoy vibrant local community access while surrounded by nature. A true Woodstock Jewelbox -- a historic carriage house reimagined with exceptional craftsmanship and modern luxury. Listing agent is also the owner.
Courtesy: Daniel Gale Sothebys Intl Rlty
516-677-0030
Nearly Six Lush, Scenic And Private Acres Located Eight Minutes From The Heart Of Woodstock! This Home Features Two / Possibly Three Bedrooms And Two Full Baths. Meticulously Maintained! Enjoy Sunrises Or Sunsets From The Wrap Around Deck. Relax And Take In All Of The Tranquility While Sitting Stream Side Or Enjoy The Changing Of The Leaves During The Beautiful Fall Season While Sipping Hot Cocoa Next To The Wood Burning Stove! The Perfect Home For Retreat Or Year Round Use. Great Opportunity For Those Looking To Host A Vacation Rental. A Must See!, Additional information: Appearance:Diamond
Courtesy: HEATHER CRONER RE-SOTHEBY'S ML
Four House Compound on 25 Acres. Welcome to this extraordinary property nestled in the heart of Woodstock, NY, which holds a rich history as it is believed to be the first farm in the Valley. Originally established as the Shultis sheep farm in 1753 this expansive 25-acre estate offers a unique blend of heritage and countryside lifestyle. With its charming farmhouse, magnificent converted barn, historic schoolhouse with two full residences, and a cozy mid-century house, this property presents a rare opportunity to own a piece of Woodstock's past.The farmhouse, steeped in history, exudes rustic charm and offers a warm and inviting atmosphere. With its classic design and timeless appeal, this residence features beautiful wood floors, beamed high ceilings and a cozy fireplace. The spacious layout provides ample room for comfortable living, while the surrounding natural beauty creates a sense of tranquility. Adjacent to the farmhouse, the converted barn stands as a testament to architectural excellence. This expansive space offers endless possibilities, whether you envision it as a studio, workshop, or a grand entertainment area. The barn's soaring ceilings, exposed wooden beams, incredible wide plank original floors and abundant natural light create an awe-inspiring ambiance that is sure to impress.Adding to the property's allure, the historic schoolhouse has been thoughtfully transformed into two separate residences. This unique feature presents an excellent opportunity for rental income or accommodating guests. Each offers its own distinct charm and character, providing a comfortable and private living space. The mid-century house, with its two bedrooms, offers a modern retreat amidst the natural beauty of Woodstock. This cozy dwelling provides a perfect blend of comfort and simplicity, allowing residents to unwind and enjoy the peaceful surroundings.Nature enthusiasts will appreciate the property's diverse landscape, including several open fields and a meandering stream. These features provide ample space for gardening, farming, or raising animals, allowing you to embrace a sustainable and self-sufficient lifestyle.Conveniently located just seven minutes away from the vibrant village of Woodstock, residents will enjoy easy access to a plethora of shops, restaurants, and cultural attractions. Whether you're seeking a leisurely stroll through the charming streets or indulging in the local culinary scene, the village offers a vibrant and eclectic experience.
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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.
