The construction of a stone house and attached summer kitchen known as Oakwood in Fauquier County began about 1785. Around 1838, a two-story house was constructed with a temple-form, Greek-Revival front, and about 1845 a two-story, stair-hall wing was built to connect the temple front to the original stone house. In 1922, the property hosted the premier running of the nationally-renowned Virginia Gold Cup Race. In addition to the race track and main residence, to which architect Alexander H. Sonnemann added Colonial Revival renovations during the 1920s, the Oakwood property boasts two secondary dwellings, a schoolhouse, a bank barn, two springhouses, two stone terraces, a goldfish pond, four foundations, a landscaped garden, three wells, stone fencing, two pairs of gateposts, and two cemeteries.