This stucco-covered home at 800 Amherst Street is known as the Toll House, for it served as the toll house for the North Western Turnpike. The Turnpike was completed around 1838, and was converted to a public road in 1884 (per Morton's The Story of Winchester in Virginia.) It is theorized the front portion of the existing building contains the original Toll House.

The land was originally part of the Glen Burnie estate, owned by Col. James Wood. The son of James Wood sold this land to Robert Steele, a Scottish immigrant. Mr. Steele was a gardener, well-known and liked in the area for his vegetables and flower beds. Mr. Steele's residence is reported to have been 338 Amherst St. in William Greenway Russell's What I Know About Winchester.