The management of existing structures is raising a number of pertinent questions to the owners and engineers. Many structures built more than 50 years ago (even those built hundreds of years ago) usually no longer comply with safety requirements of current codes, which are typically addressed in new structures. This is not necessarily only caused by a poor original design or degradation with time, but it may be, for example, the consequence of increase in actions, reducing the level of reliability of a structure. This paper focuses on strategies to be adopted for existing structures which do not comply with code requirements for new constructions (e.g., to repair, to demolish, to rebuild, etc.) on the basis of a more holistic approach that includes economic, social, and environmental considerations. To that aim, first, a brief review of the background concepts on the reliability of structures is presented, highlighting the differences for new and existing structures. Following this analysis, suitable values for the reliability index (including sustainability considerations) are proposed, as well as tailored maintenance strategies. Finally, the paper presents a case study based on a real project to emphasize the benefits of adopting such a holistic perspective.