Most of what is now Rosemary District was Sarasota's first documented African-American community — known as Overtown until the 1990s. The southern boundary of Overtown is cited as either today's 4th Street or 5th Street; the other boundaries match Rosemary District's.

The name generally associated with the initial settlement of Overtown is Lewis Colson. This formerly enslaved man arrived in Sarasota in 1884 and, as assistant to engineer/surveyor Richard E. Paulson, drove the first stake in the ground in 1885 to plat the original town of Sarasota. In 1897, Colson helped establish Sarasota's first African-American church, Bethlehem Baptist Church, by selling a plot of land at Central Avenue and 7th Street to church trustees for one dollar. Construction of the church was completed in 1899 and the building used until 1973 when the congregation moved to its current location closer to Newtown. In 1910, Colson led a group of families to establish a community near their church.

By 1920, Overtown was a thriving community. Its population grew as African-Americans moved to Sarasota for jobs in the hotel and construction industries. Its business community grew to provide goods and services that were otherwise only available to white Sarasotans. Consequently, Overtown had a variety of single family homes, commercial buildings, churches, schools and social clubhouses — many built in the mid-1920s. Some of them still remain; the most notable are shown below.

Also included below are two historically-designated Rosemary District buildings in the area south of Overtown. In 2002, Overtown was listed on the National Register of Historic Places. A copy of the Nomination Form is here. A brochure of Overtown Treasures published by Newtown Alive is here.