By referring to the European Green Deal, this paper analyzes the “intrinsic value” of cultural heritage by investigating the human-centered adaptive reuse of this heritage. This implies questions such as how to improve the effectiveness of reuse, restoration, and valorization interventions on cultural heritage/landscapes and how to transform a cultural asset into a place, interpreted as a living ecosystem, to be managed as a living organism. The autopoietic characteristic of the eco-bio-systems, specifically focusing on the intrinsic versus instrumental values of cultural heritage ecosystem is discussed in detail. Specifically, the notion of complex social value is introduced to express the above integration. In ecology, the notion of intrinsic value (or “primary value”) relates to the recognition of a value that “pre-exists” any exploitation by human beings. The effectiveness of transforming a heritage asset into a living ecosystem is seen to follow from an integration of these two values. In this context, the paper provides an overview of the different applications of the business model concept in the circular economy, for a better investment decision-making and management in heritage adaptive reuse. Matera case is presented as an example of a cultural heritage ecosystem. To conclude, recommendations toward an integrated approach in managing the adaptive reuse of heritage ecosystem as a living organism are proposed.