The naturalistic redevelopment of a former landfill appears to be one of the most interesting solutions for returning an area used over time for waste disposal to the environment. This choice, anyway, should already be considered during the design stage in order to avoid extremely artificial capping lining solutions that would not allow the growth of the desired phytocoenosis. On the Vizzolo Predabissi (Milan, Italy) landfill site, after an initial post-management phase, the environmental rehabilitation of the site was set through the elimination of the artificial superstructures and through a design of the forest landscape that allowed an evolution towards a naturalistic oasis with ecosystemic target. This article illustrates the techniques used, the challenges encountered and the management perspectives of the area, unfortunately still undefined by the public administration.