Established in 1933 as a military school for boys in grades 7-12, Bolles dropped its military affiliation in 1962 and became coeducational in 1971. The independent school is governed by a self perpetuating Board of Trustees. The School's balanced college preparatory program combines academics, offerings in the fine and performing arts, athletics, leadership and service opportunities and activities, and a nationally-known college counseling and guidance program. The boarding program, in which boys and girls reside on different campuses, complements the coeducational learning environment. After-school activities abound on each campus providing numerous opportunities and areas of interest for students.
Bolles' lower school opened in 1981 with the first kindergarten class, expanding each year until the full Pre-K through Grade 5 lower school was complete. In 1991, the School acquired the Bartram Campus, formerly the all-girls Bartram School, which allowed for the addition of a separate middle school facility and a girls' boarding section. In addition, Bolles opened a campus in Ponte Vedra Beach in 1999 to serve students from the Beaches area in grades Pre-K through 5. The School enrolls more than 1,600 students with the capacity to host 90 boarding students. An ongoing development program has made possible substantial improvements to its physical plant over the years, most recently the addition of the state-of-the-art Betsy Lovett Arts Center on the Middle School Bartram Campus and two outstanding new facilities on the Upper School San Jose Campus, the Peyton Boathouse & Rice Family Crew Complex and the Bent Student Center. Bolles Hall, the original structure on the San Jose Campus, is listed in the National Register of Historic Places and has been recognized by the Jacksonville Historical Society and the City of Jacksonville.