The school is named after the now extinct Princess Anne County, Virginia (itself named after the British Royal, Queen Anne, titled at the time and prior to ascension, Princess of Denmark) which was annexed with the founding of Virginia Beach.

In 1963, Princess Anne County was incorporated into the newly formed City of Virginia Beach and thus PAHS became the oldest remaining high school in the system.

Throughout both the 1995-1996 school year and the 1996-1997 fall semester, classes were held in a nearby vacant shopping mall known as "Celebration Station", which has since been demolished.

Shuttle buses transported students between the temporary location and the remaining, intact portion of the school/portable classrooms on the main campus.

As a result, the PA library now maintains one of the most extensive and up-to-date media collections of any Virginia Beach high school.

Princess Anne maintained its place as the highest ranked high school in Virginia Beach as well as the Hampton Roads region in the Newsweek listing of "America's Best High Schools", continuing to place in the list annually (#451 in 2012, #263 in 2011, #123 in 2010, #167 in 2008 and #213 in 2007).

This includes portions of the Thoroughgood, Thalia, Pembroke, Lynnhaven, Princess Anne Plaza and Windsor Woods neighborhoods.