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.
This landscaping created a natural-looking rise up from Menemsha Pond but required much earth to be moved. What looks like a small three-and-a-half-foot-high stone wall in the upper part of the property is actually a sixteen-foot-tall concrete retaining wall that supports the new grading and landscaping.
Similar sleight of hand lends the property a sense of implied history: The guesthouse appears added on to over time, and the primary home looks as if it has always been in its current form. A harborside boathouse, meanwhile, was similarly reimagined—updated for twenty-first-century living but with the look of the eighteenth.