Heritage is present in everyday society and it is a resource linked to social capital, economic growth, and environmental sustainability (Bandarin and van Oers 2014). Adaptive reuse is defined as “any building work and intervention aimed at changing its capacity, function or performance to adjust, reuse or upgrade a building to suit new conditions or requirements” (Douglas 2006). In Historic Preservation: Curatorial Management of the Built World (1982), James Marston Fitch points out that the adaptive reuse of historic buildings “is more economic” not only in terms of the “conservation of the energy represented by the built environment,” but also for the “relative costs of old and new built space”. Adaptive reuse can be an effective conservation strategy allowing present and future use of abandoned heritage buildings, groups of buildings, landscapes or sites, changing and enhancing their functions and adapting the existing features to new needs (Bullen and Love 2010). However, the adaptive reuse intervention should not compromise heritage values, thus the threshold of transformation versus conservation should be carefully identified. Cultural heritage adaptive reuse is a complex activity, where multiple and often conflicting values need to be considered (CHCfE consortium 2015). Therefore, adaptive reuse should be supported by adequate multidimensional and multicriteria evaluation tools which enable to deal with multiple values and needs, also considering the diverse range of stakeholders, users and beneficiaries of the interventions This study presents the structured framework for the ex-post and ex-ante evaluation of the impacts of cultural heritage adaptive reuse practices in the perspective of the circular economy. It builds on previous analysis of more than 120 case studies of cultural heritage adaptive reuse. The aim of this chapter is to identify multidimensional evaluation tools, as criteria and indicators, according to the CLIC framework of circular adaptive reuse of cultural heritage, starting from the analysis of previous studies and ex-post evaluation of adaptive reuse practices, to structure a comprehensive operational framework for ex-ante evaluation and participatory decision-support in the perspective of circularity.