These days, cultural heritage is one of the topics at the center of the urban sustainability agenda. Current economic and urbanization trends place significant pressure on urban resources, systems, and infrastructures and demand for novel approaches in governing, financing, and monitoring urban performances with particular attention to abandoned, unused, or underutilized cultural heritage, defined "waste heritage." In this perspective, cities are laboratories where innovative and collaborative approaches can be tested, and culture-led processes can be implemented consistent with circular economy principles. In order to structure and activating collaborative decision-making processes for regeneration and adaptive transformation of cultural heritage, gamification assumes a central role. The chapter analyzes the interaction among gamification and collaborative decision-making processes relevant to support the enhancement of cultural heritage and describes the Play ReCH (Reuse Cultural Heritage) platform, winner of the 2019 Welfare Che Impresa call, activated with the purpose to promote a cultural creative enterprise and include cooperation and innovation in cultural heritage regeneration processes. Play ReCH allows rethinking the management model of cultural heritage reuse through gamification processes in combining technology and reality, involving city users within creative processes.