$818,269Average Value$435Average Price per Sq Ft28Homes For Sale
Woodstock is where artistic legacy and mountain beauty meet
When people think of Woodstock, the iconic 1969 festival comes to mind, even though it was held about 60 miles away in Bethel, New York. Today, this small mountain town still attracts tourists wearing tie-dye T-shirts and flowy skirts, but Woodstock is more than just a tourist destination. “Woodstock continues to be the most dynamic and energetic destination in the Hudson Valley,” says Sean Zimmerman, associate broker at Halter Associates Realty Inc., who has been helping homeowners sell their homes for over 20 years. “We have more restaurants, music venues, art galleries and shops than any other town in the region by a long shot. I moved away when I was younger, but it’s the nature that drew me back in.”
Tucked away in the Catskills, the town’s scenic landscape draws artists nationwide. Woodstock’s art scene dates to the founding of the Byrdcliffe Arts Colony and Maverick Art Colony at the turn of the 20th century. “My grandmother lived in the Maverick colony, and my grandfather was an author,” says Laurie Ylvisaker, associate broker at Coldwell Banker Village Green Realty, who has been in the industry for nearly 40 years. “In order to raise money for a new well, they started the Maverick Festival every summer, and it was riotous. It was essentially the original Woodstock.” Over a century later, the festival still occurs at Maverick Concert Hall.
Woodstock is surrounded by wilderness and mountainous landscape.
Woodstock has peaceful art all over town that reminds people of the town's loving vibe.
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In-town homes are on walkable streets near art, music and dining
In the town of Woodstock, residential streets with modest lots fan out from Route 212. Home styles include American Foursquares, cottages, split-levels, Tudor- and ranch-style homes. Due to its proximity to the village, prices range from the upper $400,000s to over $1 million. Contemporary buildings with black siding and large windows are a newer trend, while the occasional historic Queen Anne and Victorian farmhouse are scattered in between. “Some homes can still sell for as low as $300,000 in Woodstock, but if you want an idyllic retreat, prices begin in the $700,000s and go up from there,” Zimmerman says. Rural mountain roads lead to various secluded estates on acres of land. Custom-built homes and modern log cabins with breathtaking landscapes can range from the upper $900,000s to over $4 million. On the outskirts of town, ranch-style homes can sell for under $300,000. Prospective homebuyers can also build their dream home, with plots of land selling from $10,000 for 1 acre close to town to $7 million for over 600 acres.
Woodstock cottages are charming and have great styling.
Sharkie's Meatball Shop in Woodstock is perfect for an Italian treat.
Woodstock shops gleefully line local streets and welcome all visitors.
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Children learn at well-rated schools, some with a Buddhist influence
The Onteora Central School District serves the Woodstock community and earns a B-plus rating from Niche. Kindergarten through third graders may attend Woodstock Elementary, scoring an A-minus, and fourth through sixth graders may attend Bennett Elementary, scoring a B. Onteora Middle earns a B-plus, and Onteora High receives an A-minus. Alternative schools are also popular amongst residents, including Woodstock Day School and the Middle Way School. Both are rooted in Buddhism and emphasize holistic learning, nature and interpersonal skills.
Onteora Middle School has 171 students of which 37% of students are at least proficient in math.
Reginald Bennett Elementary School has 237 students with a student-teacher ratio of 7 to 1.
Woodstock Day School has 197 students in grades PK, K-12 with a student-teacher ratio of 4 to 1.
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Woodstock has hiking trails, swimming holes and parks in the Catskills
Wooded mountain roads wind around Woodstock while the Saw Kill River’s flowing waters weave in between. The river gives way to calm pools of water, making it a popular spot for a quick dip during the summer. “There are numerous secret and not-so-secret swimming holes like Big Deep and Little Deep,” Zimmerman says. Big Deep is just one mile from the village along New York Route 212, and Little Deep is less than a mile farther along West Hurley-Zena Road.
Heading west into Woodstock, golfers can hit the range at the Woodstock Golf Club, a member-only course. Pocket parks like Village Green and Waterfall Park are scattered throughout the heart of town. Continuing west, glimpses of The Comeau Property, Woodstock’s largest public park, peak through tree-lined streets. The property spans 76 acres and is home to multiple sports fields, hiking trails along the Sawkill stream and a small stage for the community’s annual Shakespeare Festival.
On the outskirts of the village, hiking trails snake around the Catskills. “Overlook Mountain is a crowd favorite,” Zimmerman says. “It’s one of the most visited natural features in the region.” About a 2-mile hike leads to the Overlook Fire Tower, which offers hikers panoramic mountain views.
Tinker Street has boutiques, bookstores and restaurants
Tinker Street is lined with eclectic boutiques dotted with peace signs that sell Woodstock ’69 merch that attract tourists looking for a glimpse of the past. Bookstores feature publications that cater to the spiritually inclined, discussing mindfulness, meditation and herbal remedies. Yoga studios, wellness stores and the occasional psychic draw visitors and locals with enticing storefronts. “The yoga community and natural medicine are big around here,” Ylvisaker says. “I started doing acupuncture last year, and my life changed in two sessions.” Sunflower Market is a natural foods store that sells organic products along Route 212. A wellness information desk even helps shoppers decipher between the many supplements in stock. Hannaford is about 3 miles south along West Hurley Road for chain grocers.
Eateries range far and wide, but one commonality is their penchant for farm-to-table cuisine. “Silvia and Good Night are undoubtedly the two best restaurants in town and my favorites,” Ylvisaker says. Silvia’s dark, cozy interior offers a perfect ambiance for romantic date nights, while upscale American fare like oysters and smoked trout pate cater to those with a gourmet palate. Good Night features a softer, retro interior and Asian-inspired eats like Korean fried chicken and miso Caesar salad. Pearl Moon is one of the many casual spots around with regular live music, but ironically, this music-loving town recently passed a 10 p.m. noise ordinance.
Exterior view of residents walking by Woodstock Blues
Treasure Chest Antiques offers vintage finds in Woodstock.
Woodstock has many shops and a popular bookstore to enjoy.
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Local theater and music celebrate Woodstock’s legacy
“Artists would come up to Woodstock since it was 2 hours from the city in the Catskills, and the environment was open to eccentricities,” Ylvisaker says. Along New York State Route 212, Woodstock Playhouse is an iconic theater that hosts a range of plays, concerts and musicals. About 2 miles west, the Bearsville Theater and its founder Albert Grossman were major players in the 1960s music revolution. Famous artists like Bob Dylan, Janis Joplin and Johnny Cash recorded in its studio. “I actually knew Janis. She was a fun gal,” Ylvisaker says. Today, its grounds hold events that range from country music festivals to fall harvest festivals and everything in between. Music seeps into the streets weekly, whether that’s the drum circle on Sunday evenings at Village Green or live performances at one of the many restaurants around town.
The Woodstock Music Shop is a musical staple in town for records and instrument repair.
The Woodstock Playhouse is popular for theatrical productions in town.
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Scenic drives on Route 212 link Woodstock to nearby towns
Ulster County Area Transit offers free bus service throughout Woodstock, with one stop in the village and additional stops in the neighboring hamlets of Bearsville, Shady, Lake Hill and Willow. The Trailways bus also runs from the city to Woodstock. However, Woodstock is primarily a car-dependent community, and New York State Route 212 is the main thoroughfare. New York City is about a 100-mile drive along Interstate 87. Kingston is about 11 miles southeast and is also home to the HealthAlliance Hospital. Albany International Airport is about a 55-mile drive north.
Spiritual retreats at a Buddhist monastery atop Overlook Mountain
The Hudson Valley’s landscape, dotted with mountain ranges and rushing rivers, makes it popular amongst spiritual seekers. About a 3-mile drive north from the village of Woodstock, residents are greeted by colorful Tibetan prayer flags streaming along the tree line. Sitting on top of Overlook Mountain, Karma Triyana Dharmachakra (KTD) is a Buddhist Monastery and retreat center whose shrine room is enveloped in gold accents and showcases a giant golden Buddha statue.
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GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
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On average, homes in Woodstock, NY sell after 71 days on the market compared to the national average of 58 days. The median sale price for homes in Woodstock, NY over the last 12 months is $700,000, up 12% from the median home sale price over the previous 12 months.
Set on more than nine private acres just minutes from the heart of Woodstock, this elegant sprawling ranch is a rare offering where the views take center stage. Thoughtfully designed in the spirit of 1960s contemporary architecture, the home was created to celebrate its extraordinary natural setting, with sweeping vistas enjoyed from nearly every room. A substantial spring-fed pond, serene pine
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Set off a quiet lane and approached by a gracious circular driveway, this classic Cape Cod carries the particular confidence of a house that has always known exactly what it is. Spanning 1,969 square feet, the home has been thoughtfully refreshed throughout with all-new wood flooring, freshly painted interiors, updated bathrooms, and an eat-in kitchen with marble countertops and custom wood
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
More than a century in the making, and unlike anything else on the market, this extraordinary multi-residential estate began as a historic Hudson Valley farm before being thoughtfully transformed into a modern lifestyle retreat of remarkable scale and character. Over the years, musicians, entrepreneurs, and creative thinkers have called it home. Prior to that, it served as the Woodstock Farm
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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
Leigh Wagner-QuintanaKeller Williams Hudson Valley
Tucked away at the end of a quiet cul-de-sac in Woodstock, and set against a backdrop of woods, a gentle stream and mountain views, this well-maintained two-family home offers flexibility and income potential. The main residence features a welcoming living room, an eat-in kitchen, and a convenient half bath on the first floor. Upstairs, three bedrooms and a full bath provide a functional and
A rarely available large, 15+ acre parcel in Woodstock -- less than a mile from the center of town! Completely private yet moments away from restaurants, music venues, shops, golf course and hiking. A mixture of mature deciduous and conifer trees offer a forest haven, with level land, rock features and an elevated knoll building site, ready for your next chapter.Much of the heavy lifting has
Situated on a large level lot and a quiet road near the heart of town. Some recent updates and fresh paint make this 4 brdm ranch home a terrific find in today's market. A covered porch in the front and rear allow for convenient outdoor entertainment. There is also plenty of off street parking and a detached shed for additional storage. Central location just minutes to Woodstock's vibrant music
This exceptional Woodstock property offers a rare blend of privacy and convenience, just minutes from the village center. The modern main residence features 3 ensuite bedrooms, complemented by a studio and a separate guest house, for a total of 5 bedrooms and 5.5 baths across 4,000+ square feet--an uncommon offering this close to town. Designed for both everyday living and entertaining, the home
WOODSTOCK VILLAGE COTTAGE - LOCATION, CATSKILLS CHARM & VALUE! Their loss is your gain --previous buyer couldn't qualify--so here's your chance to own an authentic Woodstock retreat in the heart of the Hudson Valley's most coveted small town.Just moments from the village center, this cozy, character-filled cottage offers the perfect blend of vintage charm and everyday comfort. The
Tucked into a lush, storybook setting where a gentle stream winds through the landscape and the forest feels just within reach, this fully renovated Woodstock bungalow offers a rare blend of charm, privacy, and effortless modern living. Immaculately landscaped grounds create a true outdoor sanctuary, with multiple dining areas, a firepit for slow evenings under the stars, and peaceful vantage
The advertised rate of $10,263/month is the lowest available price, based on a 1 month(s) and 2 day(s) stay with a move-in date of February 16, 2027.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed
A Summer Like No Other Awaits You. Escape the ordinary and step into a world where luxury meets the unhurried beauty of the countryside. Nestled gracefully upon 17 pristine acres, this exquisite farmhouse retreat is a rare offering -- a sanctuary where pastoral meadows, rolling mountain vistas, and timeless charm converge in perfect harmony. Thoughtfully positioned to capture breathtaking views
**Charming Long-Term Rental in the Heart of Woodstock - Available now! welcome to your serene sanctuary in the vibrant community of Woodstock! This recently renovated ranch-style home is the perfect blend of comfort and convenience, inviting you to experience the best of suburban living. As you step inside, you'll be captivated by the airy and flowing layout, which features two cozy bedrooms
Well cared for raised ranch in desirable West Hurley location with Woodstock mailing address. Close proximity to the town of Woodstock. Available May 15.Long term tenant purchased new house looking to establish a new long term tenant. Pets on a case to case basis.Owners are licensed NYS licensed real estate brokers.
Woodstock | Private Summer Residence with Pool | 4BR/3BA | May 22-Oct 31 Set on over two private acres in one of Woodstock's most desirable locations, this fully furnished 4-bedroom, 3-bath residence is available for an extended summer stay (31-day minimum). Recently renovated. Clean lines and strong natural light. Layout offers both flow and separation, with multiple areas for living, dining,
Escape to this serene sanctuary tucked along a scenic hillside in Woodstock, just off Upper Byrdcliffe Road as you ascend toward Overlook Mountain. Just five minutes from the center of town, yet feeling completely immersed in the woods, this tranquil retreat blends nature and comfort, offering treetop views with glimpses of distant mountain peaks--and a gentle stream running through the property,
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
Enjoy Catskills living just minutes from famous Woodstock in this bright and airy single-story, contemporary cottage. A lovely stone patio and two decks, one open and one covered, invite indoor-outdoor living. All seasons, delight in viewing nature through the cottage's oversized windows. On chilly days, use the cast-iron gas stove to stay snug and warm. The open-plan living area includes a
Welcome to 6-10 Orchard Lane, Unit 7--a beautifully renovated second-floor apartment offering unique architectural character and incredible outdoor amenities, all just moments from the heart of Woodstock. Inside, the main living space boasts airy vaulted ceilings, recessed lighting, and a massive picture window framing peaceful treetop views. A charming glass French door and deep contrast trim
This beautifully renovated home offers a perfect blend of modern luxury and serene natural beauty. Set on 1.1 private acres that border a tranquil creek, the property is designed for both relaxation and entertaining. The interior features a fully renovated, modern open-concept design that seamlessly connects the living spaces, anchored by two spacious family rooms that provide ample flexibility
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