The creation of new legally protected areas brings many conflicts that distance the real landscape from the expected according to environmental law or conservation researchers. In this study, we mapped and compared the changes in Serra da Japi (São Paulo State, Brazil) throughout 40 years with scenarios of legal protection and scientific expectation on forest conservation, to evaluate the distance between them. This may allow us to infer the direction of historical changes and assist in the debate among decision makers. The results showed that most legal requirements on forest protection in the current landscape have been met. The 1960s was the period when the forest cover was closest to the desirable conservation stage. Although the Serra do Japi has maintained large areas of forests during the entire study period, human interference increased with the expansion of reforestation and urban areas, and access roads were identified as a primary potential driving forces of change. In addition, habitat loss was observed in the landscape, which can represent the first phase of a sequence of modifications detrimental to the environmental conservation of this protected area, including decision changes to land use. In conclusion, the changes evolved toward conservation expectations, but not toward the forest configuration of scientific expectation.