Headstones manifest an abundance of historic information and embody society's cultural and socioeconomic statuses over time. Cemetery research has been conducted throughout various regions in the United States, but very little has been focused on headstone analysis in the state of Florida. The purpose of this comparative research is to use a typology established by Meyers and Schultz to compare headstone attributes of Orange County, FL and establish a temporal correlation (2012). The analysis of this study has the ability to highlight societal perceptions and ideals surrounding death and mortuary practices while providing a historical context specific to the state of Florida. Data was collected from two cemeteries in Orange County, representing the headstones of 853 individuals. The methodology of this study entailed visiting the cemeteries, photographing headstones, and noting headstone attributes. Following the model set forth in Meyers and Schultz, attributes taken into consideration for this project were stone type, shape, time period, and sex of the individual (2012). In addition to assessing headstone typology for historic cemeteries, the development of best practices for photogrammetry of headstones will be examined. The questions addressed in this research will hopefully illuminate mortuary trends in Central Florida and encourage future research and literature to shift its focus to include southern regions of the United States in terms of historical Cemetery context. Additionally, practices developed in photogrammetry can aid public archaeology conservation and restoration efforts of historic cemeteries that are endangered of being lost due to external circumstances.