Cobble Hill Farm sits on 196 acres that are now within the limits of the city of Staunton, and consists of a well-preserved complex of late-19th-century agricultural buildings and an architecturally significant early-20th-century owner’s residence, as well as two tenant farms. The property is significant for architecture and agriculture. The principal building is a two-and-a-half-story masonry house with a steep gabled roof and half-timbered accents that Staunton architect Sam Collins designed in the Tudor Revival and French Eclectic styles in 1936. A summerhouse and a cistern-topped tower were designed by Collins and constructed at the same time in keeping with the house. The grounds feature a formal garden and pond along with a late-19th-century frame dairy and feed barns located near the house. The gambrel-roofed barn, built in 1937, is the first barn that Sam Collins designed. The Cobble Hill farmland was still in use for agriculture at the time of listing in the registers.