$817,030Average Value$438Average Price per Sq Ft15Homes 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:
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On average, homes in Woodstock, NY sell after 68 days on the market compared to the national average of 54 days. The median sale price for homes in Woodstock, NY over the last 12 months is $710,000, up 17% from the median home sale price over the previous 12 months.
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
Breathtaking mountain views set the stage at 26 Carle Rd in Mount Tremper, a custom 3-story Contemporary that truly reflects the spirit of the Catskills. With 3 bedrooms, 2 baths, and an open floor plan, the home offers both comfort and serenity. The centerpiece is a dramatic stone fireplace with a wood-burning insert, its chimney running through all three levels and filling the home with warmth
Located on quiet road just minutes from the heart of Woodstock, 78 Van de Bogart Road offers the perfect blend of mid-century charm and modern convivence This home sits on a premier corner one acre lot, meticulously landscaped to provide both curb appeal and a serene, private sanctuary. The upper level of this raised ranch features an open, airy layout designed to bring the outside indoors. The
So close yet so far away! Walk to town from your totally private and like-new timber frame home with soaring 23-foot ceilings and walls of windows to bring nature in. As you enter from one of Woodstock's most coveted roads, through the stately pillars, you will feel a sense of tranquility with nature on this 9.94-acre lot that is just a half mile from the village of Woodstock and less than a half
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
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,
A/O 2/12/26 - CTS. Ideal Woodstock living! This lovely 4 bedroom 3 bath private ranch is set back from the road on a quiet cul-de-sac just 3 minutes outside of the village of Woodstock. You enter and the first living space is on your right with space for a charming seating area. To your left are two bedrooms, a hall bath and a primary en suite. Through a door in the living room, you pass into a
This spectacular 35+ acre property is a rare offering. Comprised of two separate lots with access points on both Lauren Ct and Church Rd - an open canvas for your boldest vision. Whether you're a developer seeking your next signature project or a homeowner dreaming of a private sanctuary, this land invites imagination and promises possibility.A harmonious blend of mature woodlands, sunlit
Woodstock Custom Compound - Create your own private family compound on 2.44 serene acres in the Woodstock Hamlet of Wittenberg—an exceptional to-be-built offering that brings together architectural vision, artisan materials, and the craftsmanship of noted builder James Nelson. This unique project includes a three-bedroom, three-and-a-half-bath main residence, a one-bedroom guest house, and a
CAUTION ! The garage on the property has previously caught fire .Must be torn down .DO NOT ENTER THE GARAGE Prime Catskills Land Listing - HB Commercial/Residential ZoningPerfectly positioned in the heart of the Catskills, this 1⁄2+ acre parcel offers dream-worthy mountain views and unbeatable access to the region's most sought-after outdoor attractions. Whether you're planning a
Sited on a quiet country road, this beautiful 1.99-acre parcel offers a peaceful and picturesque setting surrounded by nature. Once part of an old sheep farm, the property carries a touch of history and rustic charm. Backing up to the scenic Silver Hollow Creek, it provides a serene backdrop perfect for your dream home or weekend retreat. Conveniently located, minutes to the Village of Woodstock,
Welcome to Bearsville Record House, a landmark property with a legacy deeply rooted in American music. Originally built in 1873 and once home to famed 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
This is an 86.2 acre property that is being subdivided into two- 3 acre parcels and one-10 acre parcel. The 10 ac parcel will be on the pond and the two 3 acre parcels are across the street from Yankeetown Pond. There are no houses for sale just land. There are beautiful views of the mountains and of Yankee Town Pond. The 10 acre parcel on the pond can have a structure build on it. There are 2+
The advertised rate of $18,600/month is the lowest available price, based on a 30 day(s) stay with a move-in date of May 30, 2026.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 upfront; it can be
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
The advertised rate of $7,401/month is the lowest available price, based on a 1 month(s) stay with a move-in date of April 6, 2026.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 upfront; it can be
Welcome to a home where contemporary elegance seamlessly blends with the tranquil beauty of nature. Nestled among lush greenery and towering pines, this stunning residence, worthy of features in top architectural publications, offers an unmatched living experience. At the end of a quiet, winding drive, this property reveals breathtaking views of a dramatic wooded hillside cascading down to a
With its very close proximity to Woodstock village, this is the perfect location if you're looking to engage in the vibrant artistic community yet yearn for woodsy privacy! This elegant yet simple home is very cozy with a modern kitchen, wood floors throughout, a family room in addition to the living room. and an office space. Three bedrooms are upstairs: a very large primary bedroom with 1/2
Situated on nearly an acre of manicured green grass, fruit trees, and mountainous woods in the heart of the Woodstock NY in the Catskills, this roughly 3,000 square foot 5-bedroom, 3-bathroom home is the perfect balance between peaceful nature and the higher-end comforts of being near the city. The house has a big master bedroom with large windows facing nature and easily fits a king size bed.
Luxury 3-Bed, 2-Bath Spa Retreat on over 6 Acres - Jet Tub, Sauna, Fire Pit & Handcrafted Natural Design Just 10 minutes from the heart of Woodstock and 5 minutes from the Bearsville Theater and restaurants, this stunning 3-bedroom, 2-bath retreat combines luxury, craftsmanship, and nature in perfect harmony. Every detail has been thoughtfully designed using only natural materials - stone, wood,
2 bedroom farmhouse on beautiful John Joy Road available October 1st through May 31st for 6 months or more. Set toward the back of a 3 acre meadow far from the road and bordering a beautiful forest, this charming home is just a mile or so from Woodstock Day School and 3 miles to the Zena Democratic School. Relax on the deck and take in the change of seasons and wildlife that meanders through the
Beautifully renovated farmhouse set on 4.65 private acres with seasonal mountain views. This fully furnished 3BR/2BA home features an open floor plan, custom kitchen with vaulted ceilings, high-end appliances, marble countertops, and hardwood floors throughout. Living room with cobblestone fireplace and French doors to covered porch. Screened porch and large back deck overlook lush grounds.
ANNUAL FURNISHED RENTAL w POOL Lovely, meticulously maintained 3 bd/2 ba home with flex room and finished basement on amazing road. 3 plus bucolic acres minutes to the center of Woodstock HW floors, gourmet kitchen, living room with beautiful stone fireplace. Stone patio perfect for eating al fresco Sprawling grounds and gardens. Plenty of room to enjoy hosting family and friends.
SHORT TERM RENTAL: Private, fully furnished Woodstock Oasis with mountain views, is ready to be your country getaway! On a dead-end rd. up high on a hill, this Willow home has everything you need, close to hiking, skiing, restaurants and shopping, just minutes from Woodstock, Phoenicia and the NYS Thruway, this private retreat is available beginning March 2026
AVAIL FROM SEPT 2025. Private & Serene Modern Farmhouse Near Woodstock - Nestled on a private road just minutes from the heart of Woodstock, this beautifully renovated 4-bedroom, 2.5-bathroom modern farmhouse offers the perfect blend of charm, space, and privacy. Surrounded by mature trees, stone walls, and tall hedges, this home feels like a secluded retreat while remaining conveniently close to
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