3207-3209 Route 212 Bearsville, NY 12409

Woodstock Homestead Compound in Bearsville, NY
A truly rare and wonderful opportunity awaits with this enchanting Woodstock homestead property located in the historic hamlet of Bearsville, just moments from the vibrant heart of Woodstock, NY. This serene, magical retreat is surrounded by beautiful trees, lush greenery, and the soothing sounds of the Sawkill stream, offering a tranquil escape from the everyday. The property features three unique buildings, each an architectural gem with its own character, set amidst expansive grounds that include a large, open garden ready for sustainable living—perfect for planting, raising chickens, or simply enjoying the peace of the countryside. This idyllic setting invites endless possibilities for live-work scenarios, creative spaces, or a compound.
The first building is the classic Craftsman Cottage, a charming and tastefully restored 2-story home that welcomes you with a classic open front porch, ideal for lounging on warm afternoons. At the back, an enclosed 3-season sunroom provides the perfect nook for morning coffee or quiet reflection. Inside, you'll find wood floors throughout, an airy open floor plan on the main level, and plenty of natural light streaming in from every angle. The upper floor houses 2 cozy bedrooms, wainscoted ceilings and a fully custom bath, while a large, dry basement offers ample storage space. This home is currently a successful Airbnb, presenting an excellent opportunity for passive income, or it can simply serve as your private haven in the woods.
The second centerpiece of this compound is the Converted Barn with a rich history and a rustic yet modern charm. With its open layout, high ceilings, and two smaller side rooms, this versatile space opens onto a stone patio with peaceful views of the surrounding nature, making it an ideal artist's studio, workshop, or creative retreat. This barn is not just any structure; it once hosted the Bearsville Woodworking Collective, where Pete Seeger commissioned the building of the Hudson River Ferry Sloop Woody Guthrie—a nod to the area's deep artistic and musical heritage. The barn's attic provides additional storage or the potential for expanded creative use. Surrounded by mature trees, a year-round stream, and a large meadow, the barn invites inspiration and is the perfect spot for artists, craftsmen, or anyone looking to immerse themselves in a space with incredible creative energy.
The third gem on this unique property is the Bearsville Cottage, a charming blend of historic character and artistic flair. Inside, you'll find wood beam ceilings and large artist windows that flood the open kitchen and living area with natural light. The inviting living space at the back of the cottage opens directly to the expansive backyard, providing seamless indoor-outdoor living and easy access to garden beds and open fields. One level living and the bedroom features its own separate entrance, offering privacy for guests or tenants. A woodstove in the main area adds both warmth and ambiance for those cooler Catskill nights, making this space perfect for a home office, guest quarters, or an additional rental unit for passive income.
The true magic of this property lies in its versatility and the seamless way these three distinct buildings come together to create a cohesive homestead. The expansive back garden and field area offer ample space for sustainable living, whether you dream of cultivating a thriving vegetable garden, hosting gatherings, or simply enjoying the natural surroundings. Located just a short drive from Woodstock's galleries, fine dining, and cultural venues, as well as nearby hiking trails and rail trails, this property provides the perfect balance of privacy and convenience. Whether you're seeking a live-work space, a peaceful country life, or a unique compound, this Bearsville sanctuary has it all.