This paper examines the impacts of various policy interventions in the Presidente Dutra Highway (PDH), Brazil. Using a time-series database, changes in the highway’s physical and operational characteristics are analyzed in conjunction with variations in socioeconomic and demographic indicators. A major outcome of this study is the realization that the infrastructure policy implemented in the highway has created short, medium and long term impacts of extreme complexity. These impacts are the result of a continuous development cycle in which transport infrastructure policies trigger changes in land use patterns (activities, location and density), socioeconomic and demographic indicators as well as operational conditions of the highway. The results of the case study indicate that the development cycle is only perceived because the analysis is based upon a time-series database, otherwise only operational changes could be detected. Based on the understanding of the development cycle in the PDH region, the recent implementation of the tolling system through a Public Private Partnership (PPP) scheme is assessed. It is concluded that the tolling system may create impacts in terms of initial limitations to development in all respects due to the increase in direct (user perceived) transport costs. The charging system may also result in saturation (land use and transportation) of those areas in between toll plazas.