This unique hilltop property is located at the end of a private drive, surrounded by the natural beauty of Aquinnah. It consists of two separate contemporary "Acorn houses," creating airy, light-filled environments and offers views over the expansive, meadow-like lawn that extends toward the ocean. From this vantage point, you can enjoy breathtaking views of the Atlantic Ocean, the Elizabeth Islands, a glimpse of the North Shore, and the Gay Head Lighthouse. The main house, built in 1973, features a top-floor primary suite, with the kitchen, living, and dining areas located on the main/middle level. On the first floor, there are three guest bedrooms, one of which is currently set up as a media room, and a full bathroom. Similarly, the guest house, built in 1988, includes a top-floor primary suite and an open-concept kitchen, living, and dining area on the main level. The first floor has two guest bedrooms, with one currently configured as a home gym, along with a full bathroom. In 2021, the houses were joined, expanded, and renovated by AD100 designer Billy Cotton. They are connected by a spacious wrap-around deck on the main level and by a hallway with plenty of storage closets and a large laundry room on the first level. The homes can be separated by closing a barn-style door on the first floor. This design allows the homes to function together for multigenerational families or to provide space and privacy for multiple families or guests. Both homes are equipped with a full kitchen and dishwasher. Plans for expansion are available including an additional structure, and an envelope to construct a pool.