Beautifully sited on 3.4 acres, this distinctive Chilmark home offers a rare blend of privacy, comfort, and expansive living space, ideal for entertaining, both inside and outside. From the welcoming foyer, step into the dramatic vaulted living room, where wood-paneled ceilings, a gas fireplace, and abundant natural light create a warm and inviting atmosphere. French doors open seamlessly to an expansive deck, extending the living space outdoors. Adjacent to the living area, the dining room and well-appointed kitchen flow effortlessly into a fabulous screened porch-perfect for al fresco dining or relaxing in any weather. A cozy den and full bath are thoughtfully tucked off the entrance for additional flexibility. Beyond the kitchen, a spacious mudroom with a separate entrance leads to an outdoor shower and a generous laundry room with built-ins and a sink, offering exceptional functionality for island living. The primary suite is a private wing on the main level, featuring a large walk-in closet, a full bath, and a striking double-sided stone gas fireplace that connects the bedroom to an adjoining office or den with a shiplap ceiling. With direct access to a wrap-around deck, this space is truly the crown jewel of the home. Upstairs, you'll find a large bedroom with a private deck, access to a shared full bath, and two additional bedrooms. The full-length basement, offering over 2,200 square feet, and a detached two-car garage provide ample space for storage, hobbies, or future customization. With a 5-bedroom septic in place, there is room for expansion. Just moments from the Great Rock Bight Preserve, Menemsha, and Chilmark's renowned beaches, this exceptional property captures the essence of up-Island living-private, serene, and quintessentially Chilmark.