The purpose of this paper is to propose a post-occupancy evaluation (POE) method focused on building maintenance and then to test it on two different sets of residential buildings. The paper’s three main goals are: to obtain useful data for optimizing the buildings’ maintenance plans; to search for any correlation between the occupants’ characteristics and their expectations toward the building; to study the occupants’ willingness to pay for maintenance procedures, as well as its correlation with the occupants’ perception of the elements source of maintenance (ESM). The proposed POE method for building maintenance performance evaluation (BMPE) consists of six main stages, focusing on the occupants’ opinions and their correlation with the facility manager’s. The observed case studies allowed for a preliminary validation of the POE method for BMPE. Results generically endorsed the method as a valuable tool for the rapprochement between facility management and the building’s end-users. Such findings could allow facility managers to develop more efficient maintenance plans focusing on the occupants’ real needs and expectations, raising occupant satisfaction levels and contributing to the building’s general performance.