In 1919 BK Bullard, a Lake Wales businessman and banker, purchased the 3000 acres that were to become Highland Park. Bullard hired Irwin A. Yarnell to promote the community and sell lots. Yarnell wrote many brochures and advertisements romanticizing the "azure-skyed and rainbow-tinted" Florida where "We have found the those things which spell long life and happiness. The song of birds, the perfume of orange blossoms and flowers, skys of ethereal blue, nights of velvety softness and myriad stars of surpassing brilliancy." He also assured that only "good, friendly, homey folk" were to be approved as residents of the "colony."

"La Casa de Josephina" was built in 1923 by Yarnell as a gift to his wife Josephine. This 25- room hilltop mansion overlooks the park and Lake Amoret. It is built in the "Florida Boom" style, which combines "Italian, Spanish, Gothic and nondescript elements in an eclectic and theatrical display." Josephine was a gracious hostess and La Casa was the center of the local social scene in its heyday.

A large part of the original Highland Park residents were Quakers, who were brought down to the area on "expeditions" by Alfred Major, a Philadelphia Quaker who became the unoffical ambassador for the community. Visitors were housed in "The Dormitory" which was seperated into male and female wings.

Highland Park has always been a recreation focused community, especially since the village is twined around an 18-hole golf course.