The school was founded as an all-boys' military academy in 1933 by Agnes Cain Painter, a friend of philanthropist Richard J. Bolles.

[3] 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.

Bolles operates on a two-semester academic year, with each semester split into two quarters.

In 2005, Sports Illustrated named Bolles's athletic program the ninth best in the country, and second best in Florida.

[6] Bolles has received the Florida High School Athletic Association's Dodge Sunshine Cup/Floyd E. Lay All-Sports Award (given to the best overall athletic program in each school type/size classification in Florida) 27 times.

Rogers is the all-time winningest Florida high school football coach with 466 wins.

Performing groups include Jazz Ensemble, Symphonic Band, Choir, Choral Music and Dance.