$839,482Average Value$460Average Price per Sq Ft35Homes 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 61 days on the market compared to the national average of 55 days. The median sale price for homes in Woodstock, NY over the last 12 months is $700,000, up 2% from the median home sale price over the previous 12 months.
Directly across from Cooper Lake and tucked quietly among the trees just minutes from Woodstock, this rare Catskills compound captures the kind of escape buyers dream about but rarely find. Surrounded by woods, mountain air, hiking, legendary fly-fishing waters, and the natural beauty that defines the Catskills, the property offers a unique blend of privacy, flexibility, creative space, and
OPEN HOUSE SAT 9/12 1-3PM |With nearly 14 acres, a heated saltwater pool, a separate two-bedroom ADU, and a warm character-filled main house, this Woodstock stream side country compound has been reimagined and meticulously updated within the last 5 years from soup to nuts. It is move-in ready as a weekend home, Air B&B or full-time residence. The main residence has the relaxed unpretentious
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
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
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
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
Discover 3.19 wooded acres in the heart of Bearsville, offering a rare opportunity to create your own Hudson Valley retreat just minutes from Woodstock. Set at the corner of Mt. Guardian Road and Mt. Guardian Road Extension, this fully wooded residentially zoned parcel is located along a privately maintained road in a peaceful, natural setting. Surrounded by the beauty and character that make the
Selling fully furnished. 9 Munchkin Lane: A Designer Sanctuary in Woodstock Experience turnkey luxury on 5 private, wooded acres. Featured in Instagram’s "Best of Design," this stunning estate is being sold fully furnished—including all high-end decor, electronics, and linens. Just 5 miles from Tinker Street, the home has been meticulously renovated with exposed beams, hardwood floors, and a
Discover the opportunity to create your dream escape on this serene 10-acre parcel nestled in the quiet hamlet of Willow, NY. Tucked away in nature yet just a short drive from the vibrant village of Woodstock, this expansive property offers the perfect blend of privacy and proximity. Towering trees, dappled sunlight, and the calming sounds of nature create a peaceful setting for your future home,
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
Come and see this cute-as-a-button, circa 1950 brick cape on Elting Lane, one of Woodstock's most enchanting roads! This easy-to-manage home on just shy of an acre, boasts woodland surroundings plus seasonal meadow and mountain views and fruit trees.The main floor features a light flooded living room with fireplace, an efficient kitchen with adjacent dining area with double glass doors
Welcome to the Woodstock Craftsman, a light-filled, fully furnished two bedroom, one bath mountain home nestled on a quiet 1.85-acre compound in the heart of Bearsville. Surrounded by blooming fruit trees, bluestone walkways, and serene views, this sun-drenched residence offers private stream access right across the road and comes complete with both a classic front porch and a private enclosed
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 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
Property Id: 1792319 Beautiful, quiet, one-bedroom apartment located on a secluded 4 acre lot, only 2 miles from town. Washer/Dryer in the apartment. RENT INCLUDES the following UTILITIES and AMENITIES: ELECTRIC, TRASH, WATER, FUEL OIL, ULTRA HIGH-SPEED WIFI, and STREAMING CONENT. Streaming content paid subscriptions currently include; Disney+, Apple+, Netflix, Amazon Prime, Paramount+,
Beautiful, quiet, one-bedroom apartment located on a secluded 4 acre lot, only 2 miles from town. Washer/Dryer in the apartment. RENT INCLUDES the following: ELECTRIC, TRASH, WATER, FUEL OIL, ULTRA HIGH-SPEED WIFI, and STREAMING CONENT. Streaming content paid subscriptions currently include; Disney+, Apple+, Netflix, Amazon Prime, Paramount+, Peacock, Hulu, HBOMax, Spotify, ESPN+, NFL+,… and
Architectural. Iconic. Unrepeatable. Hidden on 1.73 private acres walking distance from the heart of Woodstock, this extraordinary estate is more than a home - it's a work of art. A rare fusion of a Frank Lloyd Wright–inspired contemporary residence and an original Buckminster Fuller–style geodesic dome, this is a property designed for those who appreciate architecture, creativity, and a life
Beautifully renovated 2-bedroom loft in the heart of Woodstock. Flooded with natural light, pet-friendly, and steps from town, with nearly all utilities included (tenant pays WiFi).Welcome to this completely renovated 2-bedroom, 1-bath apartment at 5 Rock City Road, ideally located in Woodstock. This unit offers a rare combination of modern upgrades, thoughtful design, and move-in-ready
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
Beautifully designed, fully furnished 1-bedroom loft in the heart of Woodstock—flooded with natural light and steps from town, with nearly all utilities included (tenant pays WiFi).Welcome to this completely renovated 1-bedroom, 1-bath apartment at 5 Rock City Road, ideally located in Woodstock. This unit offers a rare combination of modern upgrades, thoughtful design, and true turnkey
Set on over two wooded acres, this four-bedroom, two-bath Woodstock retreat offers privacy and comfort only five minutes from the Village Green. Available as a seasonal rental for stays up to one year, the home is suited for extended escapes, remote work, or enjoying a season upstate.Renovated in 2021, the great room brings the chef’s kitchen, dining area, and living space together
*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
AVAIL FROM OCT 2026. 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
Charming, recently updated 2-bedroom, one bath cottage for rent, offering 871 square feet of comfortable living space in in the heart of Woodstock.This inviting cottage is an ideal home base for enjoying the best of Woodstock and the Hudson Valley. Spend your mornings surrounded by nature, afternoons exploring local shops, galleries, hiking trails, and farm stands, and evenings enjoying
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