The international debate on the adaptive re-use of cultural heritage sites following the Sustainable Development Goals becomes more central than ever in the implementation of circular economy models for urban policies. The new values that characterise the cultural assets, considered as the result of a collaborative process, can enhance both the manufactured capital and the human capital, and to carry out the system of relationships that bind them. At the same time, the values of historical-artistic assets and produced by community-based regeneration processes are particularly relevant when they characterise abandoned commons and cult buildings, to which communities attribute an identity and symbolic value. Starting from the definition of the concept of Complex Social Value, we propose a methodological process that combines approaches and techniques typical of deliberative evaluations and collaborative decision-making processes. The aim is to identify the complex value chains generated by adaptive re-use, in which intrinsic values can play a driving role in the regeneration strategies of discarded cultural heritage. The experimentation, tested with the project “San Sebastiano del Monte dei Morti Living Lab” (SSMOLL), activates a creative and cultural Living Lab in the former church of “Morticelli”, in the historic centre of Salerno, in southern Italy. The re-use project is part of a more comprehensive process of social innovation and culture-led urban regeneration triggered in Salerno starting from SSMOLL.