This classic contemporary retreat owned by the same family for over 2 decades is privately nestled on five picturesque acres along one of Woodstock's most coveted roads. Tucked away on a town-maintained dead-end lane, the property offers exceptional privacy and a true escape, all while remaining just minutes from the heart of Woodstock. Filled with natural light, this two-bedroom, two-bathroom home with additional flexible living space showcases soaring ceilings, warm wood floors, and dramatic floor-to-ceiling windows that frame the surrounding landscape. The open-concept main level is designed for both comfortable everyday living and effortless entertaining, featuring a spacious living room, kitchen, dining area anchored by a wood-burning fireplace, and a full bathroom. A central staircase leads to the serene primary suite, complete with an ensuite bathroom, breathtaking mountain views, and direct access to an expansive deck. Start your morning with coffee overlooking the mountains, enjoy an invigorating outdoor shower, or unwind at day's end surrounded by the peaceful beauty of nature. A second staircase from the main living area leads to the lower level, where a generous room with vaulted ceilings and skylights offers endless possibilities. Whether envisioned as an artist's studio, home office, media room, guest space, or additional living area, this flexible space is yours to create as you wish. This special home remains true to its distinctive 1980s contemporary architecture, offering a wonderful opportunity for its next owner to preserve its original character or reimagine it with a fresh, modern aesthetic. With exceptional privacy, inspiring mountain views, and incredible potential, this is a rare opportunity to create a truly special Woodstock retreat. A 3D Walkthrough Tour is available in the digital Lookbook or by request.