Cleveland Heights High School, referred to simply as "Heights," originated in 1901 on the site of the present-day Boulevard Elementary School, near the intersection of Lee Road and Euclid Heights Boulevard. Cleveland Heights High School's first graduating class, in 1907, numbered just five students. The school soon became too small for the growing student body and a new Cleveland Heights High School, designed by Walker and Weeks and fronting Lee Road just north of Euclid heights Boulevard, opened in 1916. It too was soon deemed inadequate.
The current Cleveland Heights High School at Cedar and Lee Roads was constructed in 1926, with the previous school rechristened Roosevelt Junior High. The new "Heights" was built to resemble a Tudor castle, featuring a clock tower and high columns that framed a grand main entrance. Architects and school officials tried to make sure that the new school would be large enough to accommodate the ever-growing district's needs. Indeed, a headline from a few months before the school's opening declared, "New Heights High Dwarfs Old One." The same article commented on the school's "mammoth stage" and marveled at the fact that "wires for a radio have been put in every room with a central apparatus in the office to relay outside programs." When it opened, the school was called "one of the most beautiful and commodious school edifices in Greater Cleveland."
Nonetheless, expansions to Heights High over the years were necessary to accommodate a student body that at one time approached 3,000. Perhaps the most noticeable of these changes occurred in the 1960s when a new "Science Wing" added along Cedar Road closed off the front of the school, creating an interior courtyard. As enrollment is now much lower (1,700), this long-controversial segment of the school was removed as part of a massive renovation completed in 2017.
Heights High has always been known for its excellent academics, particularly in the music and drama departments. Still, many methods of education have necessarily changed. In 2004, Heights became a pilot school for the Bill and Melinda Gates Foundation Small Schools movement, dividing the one big school into five small schools based on different learning styles and areas of focus. The experiment ended in 2015 when the small schools dissolved in favor of returning to a comprehensive high school.