The built environment faces challenges in all three dimensions of sustainable development—economic, social, and environmental. The increasing loss of functionality is a cross-sectional issue affecting buildings and settlements and their layering of social, spatial, and cultural processes. Based on a critical review, this paper aims to bridge the gap between international charters and ongoing research for built environments losing their original uses. Three emerging challenges to sustainability in repurposing are outlined from the debate, checking their incidence on research: (a) values preservation, (b) resources optimization, (c) systems effectiveness promotion. Experiences of conversion and regeneration in Japan, the Netherlands, Australia, Hong Kong City, and the USA are taken into account with the aim of comparing approaches, methods, and results. The discussion highlights three key entry points for future research on built environments: (1) communities involvement: new alliances between stakeholders, (2) the potential of technologies: combining resources’ protection and affordability, and (3) renewed productivity to preserve values and uses.

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