Rockwood, situated on a knoll overlooking the Southwest Mountains in central Orange County, is a two-and-a-half-story frame and unpainted weatherboard dwelling set over a brick English basement. Built around 1848 for Colonel John Willis, a nephew of President James Madison, the asymmetrical structure with its sharply pitched, offset, cross-gable roof is unusual for houses of the period in central Virginia. The building’s Gothic Revival influence suggests that Willis followed new architectural trends in the design of his house, especially those promoted by Andrew Jackson Downing for “cottage residences” appropriately fitted to country homes. Rockwood also displays elements of the Greek Revival style such as the classical treatment of the front entrance with its wide rectangular transom and sidelights. Located within the boundaries of the Madison-Barbour Rural Historic District, the 300-acre Rockwood property adjoining Madison’s Montpelier estate still retains its rural character and is primarily devoted to agricultural use.