Discover the perfect blend of comfort and opportunity in this charming duplex situated near the heart of Woodstock. This legal two-family home, each unit approximately 900 square feet, offers a unique chance to live in one side while renting out the other, making it an ideal investment property or a cozy haven for extended families. As you approach the property, a separate driveway for each unit welcomes you and a front yard, setting the house back from the road. The exterior, recently painted, hints at the care and attention given to this home. Step inside to find hardwood floors that add warmth and character throughout. This single level home's layout is thoughtfully designed, with one side showcasing a stone fireplace in the living room - perfect for those chilly Woodstock evenings. This side also features two bedrooms, a bathroom, washer and dryer and a kitchen with an eating area that opens to the living room. Spacious fenced-in side yard is perfect for your fur babies. The other half of the duplex like the first, has two bedrooms, a kitchen, and a bathroom, offering plenty of space for comfortable living or potential rental income. Art enthusiasts will appreciate the huge artist windows that flood the interiors with natural light, creating an inspiring atmosphere for creativity. A screened-in front porch provides a delightful spot to enjoy your morning coffee or evening relaxation. Storage is abundant with multiple sheds on the property, ensuring you'll have plenty of space for your belongings. The convenient one-level layout offers flexibility, as the property can be easily converted back into a single four-bedroom home with two kitchens if desired. Location is key, and this property doesn't disappoint. Just a three-minute drive from the Village Green, you'll have easy access to all the charm and amenities Woodstock has to offer. For those commuting to the New York City, the home is on the Trailways Bus route, for easy access. Both units currently rented. Whether you're seeking a peaceful retreat, an income-generating property, both units currently rented with a .08 Cap Rate, or a bit of both, this Woodstock gem offers the best of all worlds. Don't miss your chance to make this versatile and well-located duplex yours!
Enchanting Woodstock Compound with three separate buildings—Craftsman Home, Historic Barn & Cottage. Welcome to a truly rare offering in the heart of the Catskills—just minutes from the center of Woodstock, yet tucked away in a storybook setting of trees, meadows, and the soothing sounds of the Sawkill stream. This private 1.85-acre homestead compound blends rustic charm with modern versatility, featuring three distinct buildings, including a licensed short-term rental ready Craftsman home, a historic converted barn, and a sun-drenched cottage—each with its own character, purpose, and potential. The Craftsman Home. Thoughtfully restored and offered fully furnished, this two-story residence boasts cozy elegance and charm. An inviting front porch sets the tone for relaxed country living, while the 3-season sunroom offers the perfect perch for morning coffee or quiet reading. Inside, original hardwood floors, wainscoted ceilings, and a bright, open layout offer space for entertainment and relaxation. Upstairs, two bedrooms and a stylish bath provide a peaceful retreat. The dry, spacious basement offers extra storage or workshop potential. Currently a operating as a short-term rental, this home is truly turn-key for those seeking an income-producing property or an effortless weekend escape. The Converted Barn. Once home to the Bearsville Woodworking Collective, where the famed Pete Seeger commissioned the building of the Hudson River Sloop, Woody Guthrie, this large barn holds a legacy of artistry and craftsmanship. Its soaring ceilings, open floor plan, and natural light make it ideal for a studio, gallery, or workshop. French doors open to a bluestone patio overlooking stone gardens and field—an inspiring space for creatives or gatherings. The upper attic provides additional space for storage or future expansion. The Bearsville Cottage. A charming blend of vintage soul and creative flair, this one-bedroom cottage is perfect as a guest house, rental unit, or home office. Exposed wood beams, oversized artist windows, and a cozy woodstove make the living space both inspiring and inviting. A private bedroom entrance offers added privacy for tenants or guests, while the open kitchen and living area seamlessly extends into the backyard for easy indoor-outdoor living. The Land & Location. The Woodstock compound is fully fenced with fruit trees, open fields, and garden beds—ideal for farming, raising chickens, or simply enjoying quiet nights under the stars. A babbling creek runs year-round, adding to the property's natural serenity. Whether you're dreaming of a regenerative homestead, a live/work artist's retreat, a multi-generational family property, or an income-generating opportunity, this magical compound offers flexibility and soul in equal measure. Located just minutes from Woodstock's vibrant restaurants, music venues including the Bearsville Theater, and art galleries—with easy access to hiking, swimming, and all the natural beauty of the Catskills—this is a truly one-of-a-kind offering where history, nature, and creative potential come together. Note: Short-term rental income available upon request.

Bearsville is located in New York. Bearsville, New York has a population of 672. Bearsville is less family-centric than the surrounding county with 16.72% of the households containing married families with children. The county average for households married with children is 25.39%.
The median household income in Bearsville, New York is $101,724. The median household income for the surrounding county is $71,040 compared to the national median of $69,021. The median age of people living in Bearsville is 61.4 years.
The average high temperature in July is 82.5 degrees, with an average low temperature in January of 14.8 degrees. The average rainfall is approximately 49.6 inches per year, with 56.9 inches of snow per year.