The school was founded as an all-boys' military academy for grades 7-12 in 1933 by Agnes Cain Painter, an associate of
Richard J. Bolles. The original campus, now known as the San Jose Campus, was formed from the San Jose Hotel, a former hotel on San Jose Boulevard near the east bank of the
St. Johns River. Bolles announced that it would drop its military status in 1961 and the graduating class of 1962 ended the military era. It began admitting girls in 1971. Today, male and female students are enrolled in relatively equal numbers. The lower school opened with a kindergarten class in 1981, expanding one grade each year, finishing in 1986 with 5th grade or 1987 with 6th grade. Pre-K was added after 2005. The Bartram School became the Bolles Middle School grades 6-8 in 1991. and the school maintains separate boys and girls boarding facilities for 90 students from other states and 22 foreign countries. The school also has an active
student exchange program with schools in China, Japan, France and Spain. Participants live with the host family while attending school.
Headmasters Harry M. deMontmollin Jr. was the fifth headmaster from 1976 to 2000, the longest tenure of any president. John E. Trainer, Jr. served as the sixth Bolles President/Headmaster from 2002 to 2012, overseeing the growth of the Bartram campus, creation of an elementary school in Ponte Vedra Beach, and boosting the school's endowment. He was succeeded by Brian E. M. Johnson for the 2012–2013 school year, who was succeeded by Bradley R. Johnson '79, who was succeeded by David J. Farace who was then succeeded by the previous Assistant Head of School Tyler Hodges the ninth head of school since its founding.
Campuses • Upper School (grades 9–12) – San Jose Campus (Jacksonville) • Middle School (6–8) – Bartram Campus (Jacksonville) • Lower School (pre-kindergarten–5) – Ponte Vedra (Ponte Vedra Beach) & Whitehurst (Jacksonville) Campuses ==Academics==