The main building of our historic school was built in 1926 and was called Orlando High School. Many famous people were graduates of OHS including actor Buddy Ebsen and astronaut John Young. Business and community leaders alike have strong ties to the school as many generations have passed through the halls. Judson B. Walker was the first principal of the new school. He was followed the next year by William R. Boone.

The gymnasium was added in the late 30's. Its unusual architectural style has made it a landmark of Orlando. In 1984, upon his retirement, the gym was renamed the Robert Cluggish Memorial Gymnasium, in honor of his years of dedication to Howard. Mr. Cluggish served as a teacher, football coach, basketball coach, and athletic director during his 35 years at Howard. (He also played with the original New York Knicks!)

The cafeteria/band room was added in 1948 and the old OHS letters can still be seen on the southwest corner of the building. In 1952, Orange County Public Schools completed construction of two new high schools, Boone and Edgewater. This building was then renamed for Mr. C.E. Howard, a school trustee of earlier years (similar to a School Board member today).

Thus Howard Junior High School was established, with J.B. Bookhardt as principal. The school colors of blue and red and the Ranger mascot were selected. The first hat and boot logo used was designed by the husband of Mrs. Doris Verigan, a former assistant principal and the only female principal the school has had. (Principal Robert E. King died in April and Mrs. Verigan completed the school year as interim-principal.) Our current hat and boot logo was designed by art teacher Clinton McCracken while our school crest was designed by art teacher Valerie King. The media center was added in 1984. This one-story building was constructed in the courtyard area in the center of the main building.

In 1987, with the conversion to middle school, the name changed once again and Howard Junior High became Howard Middle School. Glen Terry was the first principal of Howard Middle School, followed by former Superintendent Ron Blocker.

The school was renovated in 2000. For eighteen months the entire school operated in 52 portables located on our athletic field. Because this is a historical building, only interior changes were made to the original buildings. In March of 2001, we moved back into a 21st century school.

Howard continues to be a leader in the field of education. In October, 2011 the Orange County School Board designated Howard as an arts magnet school. The Howard Academy of Arts became a beacon for arts education in downtown Orlando. Howard is now a zoneless magnet school where all students apply to attend through the office of School Choice. Since becoming an arts magnet school, Howard has received numerous state and national awards including Magnet School of Excellence by Magnet Schools of America, National Outstanding Arts School by Arts Schools Network, Florida Arts Model School, and National Certified Magnet School.