The core building of the immaculately maintained ensemble at Greenwood is a dignified but understated frame I-house erected ca. 1820 on property deeded in 1818 by Thomas Macon to his daughter Lucy, wife of Ruben Conway. The Macons and Conways were both locally prominent landed families and were kinsmen of James Madison who resided at nearby Montpelier. Although enlarged in 1850 with the addition of a two-story wing, and later with a modern kitchen and garage, the original portion of Greenwood is little changed. Its interior preserves simple late Federal trim. One early outbuilding stands amid a cluster of later but architecturally compatible structures. Like many historic dwellings in Orange County, Greenwood was carefully sited to take advantage of a remarkable panoramic view of the Blue Ridge Mountains. The 111 acres remaining with the property preserves the integrity of Greenwood’s setting in the Madison-Barbour Rural Historic District.