Perched on an elevated 10.69-acre site off picturesque North Road in Chilmark, this exceptional private compound pairs natural beauty with architectural distinction. Designed by renowned architect Patrick Ahearn and built by Rosbeck Builders, the 7,691-square-foot residence enjoys dramatic views across the Menemsha Hills and Vineyard Sound toward the Elizabeth Islands, with spectacular sunsets. The home centers on a soaring great room with 17-foot vaulted ceiling, fieldstone fireplace, oak post-and-beam detailing, chef's kitchen, and walls of glass opening to the landscape. Five bedrooms are complemented by two offices, a gym, bunk room, and walkout recreation room. Across the lawn, a finished barn offers flexible guest and entertaining space, a loft with full bath, and three-car garage. Open meadows, exceptional privacy, and private paths lead to Great Rock Bight, while the five-member association offers an additional 100 feet of private beach with a bluff-top camp and fire pit. Chilmark's Lucy Vincent and Squibnocket beaches and Menemsha village complete this rare up-island offering.