In the recent past, sustainable development has been considered a major issue for urban and regional studies. Adaptive reuse appears to be a practical solution for sustainable urban development. Beyond and in addition to a conceptual base consistent with circular economy and sustainability principles, how do we know if adaptive reuse is actually sustainable, provided that it constitutes a multidisciplinary and multilevel process? The present study aims at evaluating, in as much as feasible quantitative terms, adaptive reuse practices sustainability. This was attained using a set of indicators, developed combining PESTLE (the Political, Economic, Technical, Social, Legal, and Environmental aspects) and SWOT (the Strengths, Weaknesses, Opportunities, and Threats) approaches, of which the results were subjected to evaluation by experts (pairwise comparisons), following the Analytic Hierarchy Process (AHP). The indicators representing strengths and opportunities of the process were calculated to be of higher value (overall level of final cumulative indicators values; 70.4%) compared with indicators representing weaknesses and threats. Enhancing strengths and opportunities and counteracting weaknesses and threats contribute making the potential of adaptive reuse practices in urban sustainability more evident. Among analysis dimensions, political and economic aspects rank first, followed by environmental, socio-cultural, technological-technical, and legal aspect. The empirical results of this paper serve as a useful reference point for decision-making and policy formulation addressing adaptive reuse practices in sustainable development strategies.