Hibbard Casselberry

Hibbard Casselberry (1893–1969) was an American entrepreneur, real estate developer, and agricultural innovator, best known as the founder of the city of Casselberry, Florida. Born in Chicago, Illinois, in 1893, Casselberry’s distinctive first name was the maiden name of his mother, Lillian Gold Hibbard, a hardware heiress. He attended Yale University, graduating in 1916 with a degree in mechanical engineering. Following his graduation, he served as a Navy ensign during World War I.

In 1921, Casselberry married his first wife, Mary Elizabeth "Mel" Leonard. During their 1926 visit to Winter Park, Florida, Casselberry became interested in the area’s potential for real estate development and agriculture. He went to work as an exclusive sales agent for Gordon Barnett, who was planning Fern Park Estates. Eventually, Casselberry started his own company, Winter Park Ferneries.

Casselberry acquired hundreds of acres surrounding the Triplet Chain of Lakes, where he developed Fern Park Estates. His business model targeted northern retirees, offering them a residential lot combined with a small fernery or orange grove to provide supplemental income. This innovative approach set the foundation for his broader vision of a self-sustaining community. Casselberry's early developments included "Normandy" style cottages designed by noted architect James Gamble Rogers II, which garnered national publicity.

In 1940, the Florida Legislature approved a petition to incorporate the town of Casselberry. Casselberry served as the town’s first mayor for two terms and held a seat on the town council. Meanwhile, his agricultural enterprises focused on growing asparagus ferns, flowers, and Belgian azaleas, which were shipped across the country and Canada. During World War II, Casselberry’s fernery shipments could no longer compete with the growing demand for military supplies, and he switched to manufacturing parachutes for wartime use.

In 1952, Hibbard Casselberry built the Rogers designed Brightwater home near South Lake Triplet, where he resided with his second wife, Martha, for the remainder of his life.

Hibbard Casselberry passed away in August of 1969 at the age of 78.