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Just five minutes from the heart of the Village, this enchanting Woodstock retreat offers a rare blend of privacy, character, and convenience. With picturesque views of Overlook Mountain from the front of the home and a peaceful panorama of meadow, pond, woodlands, and perennial gardens unfolding across the rear acreage, the setting is both serene and inspiring. The home is rich in authentic charm and character, embracing the beauty of its natural surroundings in every season. Town records indicate 4 bedrooms and 2 baths, though the current owners have currently configured the home as three bedrooms plus a den, allowing for flexible living options. While the house is in need of some TLC and updating, its solid construction, strong bones, and exceptional location provide a wonderful opportunity to create something truly special. Thoughtfully landscaped grounds span 2.75 private acres, blending seamlessly with the natural environment to create a sense of calm, seclusion, and connection to nature—yet all just minutes from Woodstock's celebrated restaurants, galleries, music venues, shops, and year-round cultural events. With vision and updates, this home offers outstanding potential as either a full-time residence or an idyllic weekend escape. A 3D Walkthrough Tour is available in the digital Lookbook or by request.
The Upstate Lifestyle at 2059 Glasco Turnpike, Woodstock
Situated just minutes from Woodstock's vibrant village center, this property places you at the heart of a storied creative community where everyday life feels a bit more inspired. Morning coffee runs along Tinker Street become opportunities to browse eclectic galleries, vintage boutiques, and farm-to-table restaurants housed in historic buildings with character to spare. The legendary Bearsville Theater, a short drive away, offers intimate live performances in a venue known for exceptional acoustics and music history that runs deep. For outdoor enthusiasts, Overlook Mountain's hiking trails lead to panoramic Catskill views and the haunting ruins of a mountaintop hotel—perfect for weekend adventures without the commute. The Ashokan Reservoir's paved promenades provide year-round walking and cycling with sweeping mountain vistas, while the Woodstock Byrdcliffe Guild—America's oldest arts colony—hosts exhibitions, classes, and performances throughout the year. Whether you're seeking weekend retreats or embracing a full-time Catskills lifestyle, this location offers that rare combination of peaceful mountain living with immediate access to a culturally rich, authentically artistic community.
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Listing information last updated on February 10th, 2026 at 1:20pm EST.