The original plan for Oaklawn was to be a subdivision of summer homes for people coming to Florida from the North. The original owners lost the property during the depression. It is unclear as to the first owners, but the bank sold the property to a group of investors and it is assumed that the Needhams were part of the initial ownership. 

Chester Critch was the first burial in 1927. It has been understood that many graves were given to families in the beginning in exchange for work such as design of the fountain, landscaping and planning fees. 

For the first few years, the cemetery office was in the old Barnett Bank Building downtown. 

Oaklawn was acquired by the Needham family (exact date unknown). John and Rosina Needham owned the cemetery until the death of Rosina Needham in 1951. At that time the cemetery was left to a long time employee, Leonora Taylor. She began working at the cemetery in 1927 and ran the cemetery for the Needhams in their absence. Leonora and her son, Neil Taylor, built the cemetery into what it is today, purchasing many parcels of land over the years until they had 82 acres. Approximately 52 acres have been developed and another 30 acres to be developed. Wes Taylor, another family member, spent 55 years working at Oaklawn and helped to create the reputation and look that Oaklawn has today.