This up-island property—“up-island” referring to the Vineyard’s west side—consists of two houses. One, a late-eighteenth-century Cape Cod–style cottage that’s among Chilmark’s earliest homes, was lifted and placed on a new foundation, with a rear wing added in the same style as the original. The expanded and stabilized building now serves as a guesthouse. A small 1950s cottage on a hill overlooking the harbor was then converted to become the property’s main house. Work here included significant, historically sensitive additions as well as a pool, a man-made pond, and considerable regrading of the sloped site.