[Abstract: The rising economic cost of floods in the United States (U.S.) cannot be explained solely by monetary inflation or growth in coastal populations. Damaging flood events are also influenced by the way society plans for and physically develops its communities. Planning decisions dictating where structures and impervious surfaces are concentrated and the overall extent to which hydrological systems are altered may be exacerbating property losses resulting from repetitive floods. However, few studies have addressed how community planning and development decisions contribute to flood damage over time, and over large spatial scales, while controlling for multiple biophysical and socioeconomic factors. We address this lack of research by statistically analyzing 383 flood events within coastal counties in Florida between 1997 and 2001 to isolate the effects of several planning decisions and resultant features of the built environment on the amount of property damage caused by floods. Results indicate that where we choose to develop and how we protect communities from the adverse consequences of natural hazards significantly impacts the amount of property damage from flooding. These evidence-based findings provide guidance to planners and decision makers on how to build more sustainable, resilient communities over the long term