The historic abandoned hospitals present great untapped potential, not only as unique architectural testimony, but also as strategic elements for the design of the contemporary city. This study looks into the implications between the “hospital as an object”, its reuse and the ensuing processes of regeneration of the contexts which it is part of. The research starts from some preliminary questions. Is it possible to imagine that the future of abandoned hospitals passes through a “typological shift”, meaning the projection of some of the founding features of the original hospital type on a new spatial and functional organisation? What kind of future do we imagine for historic hospital buildings that have had a founding role in the definition of the organisation of modern society and that are still part of the memory and identity of the communities which they belong to? Can we assume that the restoration and reuse of old hospitals proves to be a virtuous practice, not only in terms of general “environmental sustainability”, but also thanks to the role that the great historical containers can have in the social regeneration of an urban area and in the architectural and landscape regeneration of an area? The complexity of these issues is the subject of a research based on the analysis of eighteen European case studies, which are particularly significant for the historical and architectural importance of the original building and for its final results, determined by the introduction of new contents into existing forms.