Cultural heritage is recognized as a key element for local sustainable development, contributing to the identity of territories and cultural diversity of local communities. The concept of “heritage community”, as expressed by the Faro Convention, can be enhanced in decision-making processes for the adaptive reuse and valorization of cultural heritage to build shared and sustainable development scenarios. Communities represent fundamental actors able to drive active reflection and implement the exercise of civic responsibility and (inter)cultural policies. This paper explores how local communities can have an active and effective role in the adaptive reuse and valorization of cultural heritage, through a field experimentation conducted within the Horizon 2020 project “CLIC—Circular models Leveraging Investments in Cultural heritage adaptive reuse” in the area of Rufoli, Salerno (Italy), in the perspective of the circular economy/circular city model. Starting from heritage mapping and key stakeholder’s engagement, a local working group was built, and processes of knowledge building, envisioning, and community engagement were activated. The results showed that building a heritage community can be an effective starting point for “circular” adaptive reuse of cultural heritage, stimulating not only its recovery but also community bonds, civic responsibility, and potential entrepreneurial activities for longer-term sustainable development.