$824,741Average Value$467Average Price per Sq Ft37Homes 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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On average, homes in Woodstock, NY sell after 73 days on the market compared to the national average of 56 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.
You won't believe the welcoming energy in this house, just 10 minutes from the center of Woodstock. Light pours in from all sides of this quintessential raised ranch off a scenic road and on a beautifully paved private driveway. Offers open-plan living space with sliders to a large deck, perfect for alfresco dining or watching the sun set over the Catskills. Come and check out the idyllic views.
There's a particular kind of quiet in Willow -- the hush of wind through the trees, the far-off ridgeline, the sense that the world has politely paused. Tucked into these woodlands, a renovated, three-level log home rewrites what a cabin can be: the honeyed warmth of timber, yes, but paired with clean-lined updates, contemporary comforts, and an openness that feels closer to a modern mountain
Million-Dollar Views as Far as the Eye Can SeePerched privately on 5.1 acres with breathtaking 100-mile panoramic views, this extraordinary log home is a true architectural masterpiece. Constructed from massive 18 to 20 inch in diameter logs that required cranes for assembly and individually placed upon an expertly engineered foundation, this remarkable residence represents a level of
A Rare Byrdcliffe-Era Magical Retreat with Artistic Legacy Built in 1905, just as the historic Byrdcliffe Arts Colony and the Art Students League of New York's renowned summer school were taking root, this extraordinary three-bedroom, two-bath, one-of-a-kind residence is a rare architectural treasure deeply woven into Woodstock's creative history. Rich in authenticity and soul, the home
Major price reduction. Seller says sell!!Woodstock Village living doesn't get much better than this. Perfectly positioned on a quiet no outlet street just moments from the heart of town, this beautifully renovated three-bedroom, two-bath home offers the rare opportunity to enjoy both nature and village life without compromise. Step inside to bright, sun-filled interiors and an open, welcoming
28+ Acres in Woodstock with Views Set at the foot of Mt. Tobias and surrounded by protected state and conservancy land on all sides, this exceptional 28+ acre parcel offers a rare opportunity to build with lasting privacy just minutes from the heart of Woodstock. An established driveway leads to a thoughtfully cleared build site where expansive valley and mountain views create a stunning backdrop
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
Exceptional 3 bedroom, 4 bath light-filled contemporary home offering refined nouvelle living set on over 4 private acres in Woodstock, NY. This home has had a complete interior high-end designer renovation that has been thoughtfully curated with sophisticated finishes and fine craftsmanship blending seamless luxury, comfort, and architectural elegance. A dramatic great room framed by soaring
This classic contemporary retreat owned by the same family for over 2 decades is privately nestled on five picturesque acres along one of Woodstock's most coveted roads. Tucked away on a town-maintained dead-end lane, the property offers exceptional privacy and a true escape, all while remaining just minutes from the heart of Woodstock.Filled with natural light, this two-bedroom, two-bathroom
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
Classic Woodstock Farmhouse with Pool, Valley Views & Storybook Grounds Come settle into the quintessential Woodstock lifestyle, a warm, welcoming farmhouse that invites both quiet mornings and spirited gatherings. The wide rocking-chair front porch sets the tone from the moment you arrive, the perfect place to linger with friends over a drink or lose yourself in a book through the long, golden
Exceptional 3 bedroom, 4 bath light-filled contemporary home offering refined nouvelle living set on over 4 private acres in Woodstock, NY. This home has had a complete interior high-end designer renovation that has been thoughtfully curated with sophisticated finishes and fine craftsmanship blending seamless luxury, comfort, and architectural elegance.A dramatic great room framed by soaring
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
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
Creekside Modern Home with Mountain Views Near Woodstock Surrounded by mountains with private access to a year-round creek, this thoughtfully designed home feels deeply connected to its setting while offering comfort, privacy, and modern convenience. Built in 2017 and significantly expanded and upgraded in 2022, the property blends clean contemporary design with warmth and functionality. Large
The advertised rate of $10,923/month is the lowest available price, based on a 1 month(s) and 2 day(s) stay with a move-in date of February 17, 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
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,
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
*SUMMER & FALL RENTAL* (AVAIL May 25 - Oct 31, 2026) // This unique hilltop property includes two separate structures -- a beautifully designed three-bedroom main house and a private loft guest house offering flexible space so you have accommodations for up to 10+ guests. Tucked away on a private hilltop ridge just under three miles from the pulse of Woodstock, 55 Nordic Drive is a secluded
Here's your chance to spend a flexible season staring at one of the most incredible views this seasoned agent has ever seen in the Catskills. Featured in the book Woodstock Handmade Houses, this beautiful and private home on Overlook Mountain is the perfect marriage of Swedish minimalism and antique rustic materials. The panoramic views reveal themselves immediately upon entering the home. The
Located on one of Woodstock's most desirable roads sits this classic contemporary set on 5 acres. Privately situated on a town-maintained, dead end lane for that ultimate get-away feeling, this light-filled, two bedroom, two bathroom home with additional flex space, features soaring ceilings with solid wood floors, flooded with natural light from floor-to-ceiling windows. The main living area
Escape to your own private retreat nestled among mature trees and bordered by a tranquil stream. This unique property offers an extraordinary blend of nature, privacy, and relaxation, creating a setting that feels worlds away from everyday life. Designed with a Zen-inspired aesthetic, the home features a remarkable spa-like bath suite complete with a slate walk-in shower, bamboo accents, river
AVAIL FROM SEPT 2025. Secluded Mountain Chalet with Breathtaking Views and Poolside Lodge - Set atop nine private acres, this stunning mountaintop chalet offers a rare combination of serenity, seclusion, and spectacular views. A long, private driveway winds through the property, leading to a retreat unlike any other. The property features a three-story main house and a separate two-story Poolside
Woodstock Summer 2026! Perched on a hill with panoramic views of the Cooper Lake this residence seamlessly blends European sophistication with Woodstock country vibes. Designed with an emphasis on light and line, the home features an open-concept layout framed by floor-to-ceiling glass, ensuring the mountain and lake vistas remain the focal point of every room. The interior aesthetic is a refined
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