388 390 Wittenberg Road, Bearsville, Ny, 12409

A rare opportunity just minutes from the heart of historic Woodstock, this exceptional country compound pairs the timeless character of a beautifully updated farmhouse with the privacy and tranquility of an estate-like setting. A long private drive unfolds through peaceful, park-like grounds where meadow, mature woods, gardens, and abundant nature create a remarkable sense of seclusion so close to town. At the center of it all, the classic farmhouse has been thoughtfully transformed for modern living while preserving the warmth and authenticity that make a Woodstock home so distinctive. An expansive wraparound porch and deck invite long afternoons outdoors, elegant entertaining, and evenings beneath the stars from the hot tub. Inside, natural light pours through generous windows and skylights, illuminating an open and welcoming interior where a spacious living room flows effortlessly into the dining area and striking gourmet kitchen, anchored by a dramatic stone island. A soaring vaulted living room overlooks the meadow and woods and features a woodstove and direct access to the deck, creating an extraordinary gathering space - or the possibility of a main-level primary suite. A separate den offers an ideal home office or studio, while a gym/yoga room, laundry room and full bath add versatility to the first floor. Upstairs, three bedrooms and another full bath retain the farmhouse’s old-world charm, including a serene and generously proportioned primary bedroom and a second bedroom with its own inviting nook.
Adding another dimension to this extraordinary property is a beautifully maintained storybook cottage, privately positioned toward the front of the grounds with its own parking, patio, and yard. Currently licensed for Airbnb use, the cottage offers an appealing opportunity for short-term rental income while remaining equally suited as an elegant guesthouse, private retreat, or longer-term residence. Its charming two-story interior features a comfortable living room, eat-in kitchen, full bath, and two upstairs bedrooms, creating a completely independent destination within the property. With hiking, nature preserves, and the Catskills landscape nearby - and the galleries, restaurants, shops, music, and cultural life of Woodstock only a few miles away - this is a particularly rare convergence of location, privacy, architectural character, and flexibility. Whether envisioned as a refined full-time residence, an exceptional weekend escape, or a private country compound with a valuable guest and rental component, this turnkey property captures the essence of elevated Woodstock living: a classic farmhouse reimagined for today, surrounded by natural beauty, with space to retreat, gather, entertain, and simply enjoy an extraordinary place to call home.
A 3D Walkthrough Tour is available in the digital Lookbook or by request.