Negligence of former industrial sites (“brownfields”) has adversely impacted urban landscapes throughout the industrialized world. Brownfield redevelopment has recently emerged as a sustainable land use strategy and impetus for urban revitalization. This study presents a system dynamics model of the redevelopment process that illustrates how delays compound before realizing financial benefits from investment in these core urban areas. We construct a dynamic hypothesis, in which brownfield redevelopment activities are dependent upon funding and in turn bolster tax base through job creation. Drawing on previous studies, barriers to brownfield redevelopment are explored, including fear of liability, regulatory concerns, and uncertain cleanup standards and funding mechanisms. We model a case study of redevelopment in the State of Michigan (USA), which is informed by data from the Department of Environmental Quality (MDEQ) and U.S. Conference of Mayors brownfield surveys. Stock-flow structures represent phases of redevelopment, with diverted streams for sites in which no contamination was found (false alarms) and those with excess contamination level. The model is used to examine the point at which cumulative tax revenues from redeveloped areas exceed cumulative expenditures on brownfield redevelopment under different levels of funding availability.