The Wilson House is significant as an example of early Sarasota architecture and as the home and medical office of C.B. Wilson. In 1877, A.M. “Gus” Wilson settled in Miakka, then part of Manatee County, where he served as postmaster, Indian agent, census enumerator, and state legislator, became a vital participant in the campaign to create Sarasota County, and later became its first tax assessor. He and his wife Callie had six sons and four daughters, including Cullen Bryant, or C.B., who became a prominent Sarasota doctor. In 1907 Dr. Wilson purchased the house on the southeast corner of Ringling Boulevard and South Orange Avenue from local architect Edgar Ferdon, and it served as both the Wilson family home and his medical office. He and his wife Fannie, the daughter of Sarasota pioneer C.L. Reaves, had two sons born there. When their first son, Clyde H., was born in 1908, the house was a one-and-a-half story structure, and by the time their second son, Reaves, was born in 1913, Dr. Wilson had enlarged it, first by adding a garage for Sarasota’s first automobile, his 20-horsepowered REO Roadster, and then by adding a framed second floor. Active in the community, C.B. served as president of First Trust Company of Sarasota and as a board member of Sarasota Memorial Hospital from its founding until his death in 1941. Reaves followed his father into medicine, served as a surgeon in World War II, then returned to Sarasota and practiced in the Wilson House. Clyde Sr. became a legal and civic leader who helped financially support the Bayfront Park project that included the Municipal Auditorium, was a founding member of the Sarasota Jaycees, and was active in legal and historical associations. Clyde H. Wilson, Jr. later played an instrumental role in saving the house from demolition, and in 2004 he, his sister Paula C. Wilson, and others contributed to relocating it to its current site on land formerly owned by the Wilson family.