This book examines the role of the evaluation models in decision-making processes for the construction of circular cities in the digital revolution. In particular, the book explores the need for a rethinking of development models proposed by the circular economy which requires the valorization of natural, social and economic capital. Urban environment represents a crucial field of analysis in which applying the circular-economy principles in order to steer a course towards a sustainable economy characterized by processes meant to create value instead of extracting it, which put a step forward in the pathway towards a better future in terms of economic, environmental and social effects and desirable outcomes. In this context, the design of urban regeneration processes and housing environments requires the adoption of inclusive analysis/assessment models combined with the structuring and organization of public/private investments that can contribute to creating positive natural and social impacts as well as economic and financial returns. This fundamental paradigm shift is accentuated in the current context, in which the digital revolution is reinventing the future and calls for a rethinking and reformulation of value systems in the era of technological process innovations, while respecting economic, natural and social ecosystems.