Existing maintenance policies have several limitations, mainly due to the lack of knowledge regarding the durability and performance of buildings. Usually, the maintenance policies are insufficiently accurate, neglecting the risk of failure over time and the global costs associated with repairs. In this study, a condition-based maintenance model, based on Petri nets, is proposed to evaluate the impact of three maintenance strategies of ceramic claddings in pitched roofs (CCPR): MS1—only total replacement; MS2—composed of total replacement and minor intervention and MS3—composed of total replacement, minor intervention and cleaning operations. In this study, 146 CCPR were inspected in situ, with a total area of 43,991.6 m2. The remaining service life of the CCPR; the global costs over the claddings’ lifetime (considering inspection, maintenance, replacement and disposal costs); the claddings’ degradation condition and the number of replacements during the time horizon are used to evaluate the performance of the different maintenance strategies through a simplified multi-criteria analysis. The results show that the gains in performance, in terms of expected service life and durability, of the consideration of preventive maintenance actions (minor interventions or cleaning operations) outweigh the increase of the operation costs.