In recent decades, there has been a growing awareness of the importance and desirability of fostering the involvement of more actors, and in particular local communities, in the protection of cultural heritage. Since universities have long been asked to become promoters of actions aimed at increasing society’s general level of well-being through interventions with cultural, social, and educational implications via technology transfer and knowledge sharing, a mutual collaboration between different researchers of the Politecnico di Torino, public administrations, and local communities has been consolidated over the last few years to provide a proactive contribution to both the preservation of cultural heritage and the social and economic development of the territories. A new educational methodology with direct and mutual collaboration between teachers and students, local communities, and policymakers was tested. The experiences conducted so far testify to the university’s ability to fulfil its training, research, and “Third Mission” tasks, both by responding to the needs of the territory and by transmitting up-to-date work methodologies, disciplinary skills, attention to context, and dialogue with local communities. The work carried out, appreciated by citizens and municipal administration representatives, was able to provide hints and stimuli for new opportunities and actions to be undertaken, foreshadowing possible development trajectories of the contexts investigated.