Dr. Robert Thomas, a prominent Orange County physician, constructed Oakley in the Greek Revival style in 1843. His daughter Sarah (Sally) Thomas Browning and her husband, G. Judson Browning, later owned it. George W. Bagby (1828-1883), Southern Literary Messenger editor and well-known humorist, cast Judson Browning as the fictional narrator of "Jud Brownin's Account of (Anton) Rubenstein's Playing" and "Fray Devilo," stories describing a piano concert and an opera in rural dialect. This genre remained popular into the 20th century. Browning organized the Orange Rangers during the Civil War and afterward served in the Virginia House of Delegates, 1865-1867.