The Bayard-Bouchelle House links two of Chesapeake City’s best-known family names, the Bayards and the Bouchelles, both related to regional patron Augustine Herman. The property’s earliest record is the April 1854 ninety-nine-year lease of the lot, buildings, and improvements granted by Richard H. Bayard to Peter and Sarah Bouchelle. That lease ended with another land record in November 1857, and five months later Bayard sold the house and lot to the now widowed Sarah Bouchelle, who later remarried into the Deshane family. The two-story rear section may be an addition rather than part of the original three-story house, but the L-shaped construction typical of the era appears clearly on 1877 fire insurance maps of Chesapeake City. Its distinctive rounded front porch and floor-length front windows are believed to be early 20th-century improvements.