This chapter presents the case of a historic industrial district in the city of Bologna (Italy): Roveri District. Here a transition process towards a smart sustainable district has been started and a systemic, integrated and bottom-up approach put the basis for the conception of the sustainable model in order to transform the district into Roveri Smart Village. Roveri Industrial District was settled in the early '70s as an industrial area in the outskirts. In the last years, the whole district was incorporated into the southern urban area of Bologna. Currently, Roveri Industrial District represents one of the Italian Metropolitan areas with the highest concentration of small and medium-sized enterprises. Nevertheless, district management does not already exist. Recent economic contingencies have induced a general, not coordinated transformation of the past industrial structure. Therefore, the combination of regeneration and sustainability actions is the main challenge to which Roveri F. Cappellaro (B) ENEA,