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.