The school opened in 1886 on the second floor of Boyd’s Hall, currently where City Hall stands. In 1890, a frame school building was built at the corner of Central Avenue and First Street. When the student population reached 200 in 1912, more space was added onto the structure. Three years later a brick building replaced the wood-framed ones to make room for all elementary and high school students in 12 grades. In 1922, an eight-room structure for the high school was built on Fourth Street, the present annex at Denison Junior High School. In 1925 a large stucco building was built on the adjacent lot for the high school, and the smaller building became a junior high department. The current structure was built on Sixth Street in 1955 on a tract of land. The late 1980s and 1990s saw a tremendous expansion of the campus, including a new gymnasium, music building and administrative offices. The full reconstruction of the school commenced in the fall of 2009. All of the original campus was demolished and replaced with a total of four new buildings. An estimated 24 million dollars was spent on the construction and the new building boast two stories, new laboratories, kitchens, and art rooms. Most recently, it was announced on January 4, 2012, that Winter Haven High School became a "B" school. This was a major achievement and showed that school was and still is making progress as it continues to be a "B" school. The School also offers the Cambridge Program from the university of Cambridge in England. It is a great program that offers students an opportunity for world wide leading universities. The school held a “Celebrate Blue and Gold” event Sept. 15, 2006 to mark the school’s 120th anniversary.
Athletics
The girls basketball team won the state championship in 2005, 2007, and recently in 2016. In 2015 the school made their first ever girls weightlifting team.
Band
The WHHS band program, which dates from 1936, consists of the "Pride of Winter Haven" Marching Band, including the Devilette Dance and Flag Ensemble, the Symphonic and Concert Bands, "Messengers" Jazz orchestra, Percussion Ensemble and many student-led ensembles. The Winter Haven High School Marching Band, also known as "The Pride of Winter Haven," performs at football games, marching band competitions, community events and local and national parades. It has performed in many national events, including the Washington DC National Cherry Blossom Parade in the 1960s, the Macy's Thanksgiving Day Parade in the mid-1990s and then later in 1998 St. Patrick's Day Parade in New York City. In 2011 they received their 12th consecutive FBA "Straight Superiors" at the District 12 marching competition. The Symphonic Band performed at Carnegie Hall in New York City on May 24, 2008 with two other ensembles, The Caltech-Occidental Concert Band from California and Jackson High School Wind Ensemble from Washington.
Notable people
Trey Mancini, MLB baseball player for Baltimore Orioles
