8 Pine Grove Street, Woodstock, NY 12498

Discover the essence of refined country living in this impeccably restored 1920s farmhouse, perfectly positioned in the heart of Woodstock, NY—just 90 miles from New York City. Professionally designed and legally configured as a two-family residence, this unique property offers the rare opportunity for an immediate live/work lifestyle, a multi-generational retreat, or a lucrative rental investment in one of the Hudson Valley's most sought-after towns. Set on a spacious, beautifully landscaped corner lot along a quiet, tree-lined street, the home balances vintage charm with modern functionality. Inside, original wide-plank pine floors and whitewashed ceiling beams create warmth and character, while custom finishes throughout add thoughtful sophistication. Every room is individually climate controlled, offering comfort and efficiency year-round. The home has been freshly painted, both inside and out, and features a brand-new roof. With five bedrooms, four full bathrooms, and a dedicated office, there is abundant space for creativity, relaxation, and entertaining. Each unit offers its own private entrance and fully fenced, landscaped backyard complete with a fire pit—creating peaceful, separate outdoor sanctuaries ideal for lounging or hosting under the stars. Off-street parking adds convenience, while the location places you just minutes from Woodstock's iconic restaurants, galleries, shops, and live music venues, as well as the Trailways bus to NYC. A short drive leads to Catskill Mountain hiking trails, ski areas, swimming holes, and the historic Hudson River waterfront. The lower Garden Apartment is a 3-bedroom, 2-bath retreat that includes an open-plan living and dining area overlooking the private garden. It's beautiful primary suite features cathedral ceilings, skylights, an ensuite bath, and a private deck built around a living tree—an enchanting detail that underscores the home's harmony with nature. A vintage clawfoot tub, fully equipped kitchen, and additional office complete the space, making it equally functional and charming. The upper Treetop Apartment is a serene 2-bedroom, 2-bath haven. The open-concept layout flows seamlessly to a private balcony perched among the trees. A sleek new kitchen, a spacious primary bedroom with a meditation or office nook, and a bright guest room with an ensuite bath make this a truly tranquil space. Furnishings in both apartments are available for purchase, offering a turnkey solution for immediate occupancy or rental. This extraordinary property is far more than a home—it's a versatile sanctuary that offers the perfect blend of style, privacy, and community. Whether you're looking to settle in full time, escape on weekends, or invest wisely, this one-of-a-kind Woodstock residence invites you to live, work, and play in one of the most creative and celebrated small towns in the world.