Fancy Hill is one of the seven fine 19th-century houses referred to as the “Seven Hills of Rockbridge County.” Constructed in 1821, Fancy Hill is significant for its architectural form and its historical association to notable Rockbridge County institutions, such as the Rockbridge Agricultural Society, organized at the residence in 1827, and the Fancy Hill Academy of the 1870s. The house and property at Fancy Hill evolved through additions in 1831, the 1840s, and 1936. Consistently high quality craftsmanship is clearly evident, whether it is the Federal-style 19th-century house or the Depression-era farm buildings. Along with Fancy Hill, the Seven Hill houses include Cherry Hill (1790), Fruit Hill (1822), Rose Hill (1824), Hickory Hill (1825), Clover Hill (1834), and Liberty Hill (1836). These architectural icons of Rockbridge were constructed for the Welch, Greenlee, and Grigsby families.