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 sitting area 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 and access to a shared full bath, along with 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 livingprivate, serene, and quintessentially Chilmark. First Floor: The foyer entrance opens to the cathedral-ceiling living with a gas fireplace, skylights, and large picture windows which provide an abundance of natural light. The dining room and kitchen are open to the living room for easy entertaining. Enjoy the fabulous outdoor deck and screened porch, accessed through the dining and living rooms. There is a den and full bath off the entrance, and the laundry is conveniently located off the kitchen with access to the outdoor shower. The piece de résistance is the primary suite, which spans the entire back side of the house. There is a walk-in closet, a full bath, and a double-sided gas fireplace servicing the bedroom and a shiplap ceiling office/sitting area. A wrap-around deck completes the primary suite. Second Floor: Three bedrooms and a shared full bath occupy the second floor. One of the bedrooms boasts a private deck and has direct access to the bath.