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The research is based on the analysis of recent experiences of participative processes in the reuse and maintenance of contexts considered as “urban waste,” focusing on their role in smart sustainable development processes. The recognition of discarded urban spaces/buildings as regeneration opportunities opens up new perspectives on the communities’ commitments and responsibilities, in new governance models. These experiences, better known as “commons,” highlight the active role of communities in establishing new unconventional forms of value creation and production based on circular processes and interdependences between city and communities. Circularization and synergies are the fundamental precondition for smart sustainable development. Assuming the Historic Urban Landscape (HUL) approach as general framework, the phenomenon of commons represents an opportunity to make it operational through an integrated methodology based on the recovery of the environment built according to an inclusive and hybrid approach, configured by culture and shared with local communities. In this perspective, this contribution proposes an evaluation framework not only to monitor the results and impacts produced by these experiences, but also to stimulate and improve awareness, self-learning and self-evaluation processes of the actors involved in regeneration processes toward a smart sustainable development.