The purpose of this paper is twofold. First, the strong connection between adaptive reuse and sustainable development is addressed; the economic, cultural, and environmental contributions of adaptive reuse could be successful proponents of sustainability-driven development, or redevelopment, of the built environment. Second, within this framework, some criteria emanating from the foundations of sustainability, which are included in the analysis of potential adaptively reused units, are discussed. The paper concludes by outlining the statistical importance of the specific criteria concerning such analyses, the knowledge of which could be valuable to decision makers and involved stakeholders aiming to achieve successful sustainable adaptations. Although the majority of the findings presented in this paper derive from the application of multiple regression analysis in the context of empirical research based on the specific region of Cyprus, the implemented methodology could be applied to a broader context, hence leading to more universal observations.