The negligent upkeep of many abandoned industrial sites (“brownfields”) throughout the twentieth century has had grave impacts on the urban landscape of American and European cities. In recent years, brownfield redevelopment has come to be viewed as a strategy for sustainable land use and urban revitalization. This study assesses the feasibility of the construction of a dynamic simulation model of urban brownfield redevelopment. Literature surrounding brownfield redevelopment is reviewed and used to construct a dynamic hypothesis of brownfield redevelopment as it relates to site liability, economic viability, and availability of redevelopment funding. Finally, an initial system dynamics model of the brownfield redevelopment process is constructed. This quantitative analysis is performed using the 2003 US Conference of Mayors brownfield survey, which serves as a dataset on brownfield distribution and average site size. We conclude with suggestions for the extension of the model to capture spatial feedback in order to assess redevelopment effects on the surrounding matrix of urban land-uses.