This waterfront Eastern Shore plantation is distinguished by its early manor house, a rambling frame structure built in several stages. Its evolutionary quality is typical of the architecture of the region where the various generations of owners are reflected in the fabric of their dwellings. Oak Grove has a mid-eighteenth-century, gambrel-roof core to which a Federal wing was added about 1811, and a matching wing with Greek Revival trim was added around 1840. A complementary 1940s wing and alterations in the oldest section echo the Colonial Revival ethic of the mid-twentieth century. The Colonial Revival flavor is heightened by an eighteenth-century- style garden designed by Richmond landscape architect Charles Gillette. Four early outbuildings and a cluster of wooden, twentieth-century farm buildings preserve the rural flavor of the property. Noteworthy is Oak Grove's scenic setting on a narrow peninsula overlooking the Chesapeake Bay. - NRHP, October 1992