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While sustainable development has long been a subject of study, only in recent years have international organizations, nations, regions and communities intensified their action towards it and engaged in efforts to make its principles operational. The attempts to design policies and strategies and define measuring instruments for implementing sustainable development and reducing the uncertainty of the implementation process have been not completely successful and have been mostly confined to the environmental dimension of sustainability. Innovative strategies, policies and measuring instruments need to be develop, starting from the elaboration of indicators and indices to monitor progress towards the sustainability goals. Several instruments are available in the scientific and technical field; however, no consistent methodology to measure sustainability accurately has yet emerged.This study proposes a methodology to measure sustainability across its three declinations: environmental, economic and social. The proposed methodology focuses on a multi-criteria evaluation framework based on the Utility Value Analysis technique, using predetermined criteria and a set of indicators, and it is supported by a web application that simulates multi-criteria decision-making processes. The aim is to provide decision makers with a flexible tool for evaluating investment projects in very different contexts, such as, for instance investment in physical or social infrastructures or culture. Results based on the application of the proposed methodology to ongoing investment projects show that the methodology can meet the needs for flexibility and simplicity in assessing and measuring sustainability.