This paper investigates the relationships between Circular Economy, Circular City and Cultural Heritage Adaptive Reuse in terms of evaluation methods. Circular economy is the economy of natural bio eco/system that reduces entropy, increases resilience and stimulates cooperation between components (it starts from the search of efficiency, but it is based and it stimulates cooperation / synergies). It is the economy of co-evolution, co-operation, co-ordination of actions for a common interest. Circular city is the concept of city as a living complex dynamic circular system, cities able to self-organize, self-manage, self-govern themselves. Cultural Heritage is the memory itself of the urban living system; it is the heart of the city, its identity conserved over the centuries. This work is focused on the structuring of a systemic evaluation framework based on criteria and indicators to assess Cultural Heritage Adaptive Reuse impacts in the perspective of the Circular Economy. Pilot applications in Italian and Belgian case studies are presented.