The aim of this paper, in line with the 2030 European Agenda and 2021 Italian “Recovery and Resilience Plan” objectives, is to define an evaluation methodology and tool to support public administrations to detect buildings, currently unused or underused, that might be apt for transformation interventions. The focus is on historical Italian healthcare buildings since these show widespread decay and neglect. A five-step methodology has been developed: screening of public assets; classification, evaluation, and identification of buildings, based on the “potential index”; GIS mapping and inventory; selection of buildings for in-depth analysis; BIM digitization and definition of the “transformability index”. In the fifth phase, an evaluation tool is integrated into the BIM software to automatically calculate the transformability index of each building using six indicators: usability, fragmentation, modifiability, roof implementation, external envelope, and window-to-wall ratio. The “transformability index” helps define the most appropriate buildings to intervene with for reuse. Building transformation is connected to construction features and layout organization and it is limited by architectural, structural, and artistic constraints.