It is imperative that the maintenance possibilities of a building be considered at the design stage, this will enhance ease of maintenance of such buildings and prevent building failures resulting from design inadequacies. This study analyzed the design configurations of selected buildings in Obafemi Awolowo University, Ile-Ife; the maintenance problems traceable to design; and also determined the impact of design related problems in the maintenance of the buildings. This was with a view to providing information that could enhance the maintenance of future buildings in the study area. The study used primary data obtained from physical observations of the selected buildings and secondary data from existing maintenance records. There were thirteen (13) faculties with forty-four (44) buildings and eighteen (18) lecture theatres within the study area. Using stratification based on design configuration, twenty-seven (61%) faculty buildings and ten (56%) lecture theaters were selected as sample size for the study. Forty five questionnaires were administered on the staff of Maintenance Unit, building occupiers and the staff of Physical Planning and Development Unit (PPDU) of the university. Data collected were analyzed using frequency counts and percentages. The results of the study revealed that in-built access for maintenance operations was provided for only 31% of the total building facades. The problems encountered in the management of maintenance operations on the defective elements were traceable to factors such as environmental impacts (13%), structural stability (11.1%), functional failures (10.5%), and inaccessible defective portions (9.3%). Others were aesthetic considerations (9.3%), users’ impacts (9.3%), choice of inappropriate construction materials (8%), and building shapes (6.8%). The identified physical impacts traceable to design inputs were moisture stain (2.92%), weeds on building elements (2.63%) cobweb stains (2.34%), broken concrete fins at stairwells (0.15%), plumbing defects (0.44%), blocked drains (0.15%), and undersized roof gutter (0.15%) among others. The study concluded that problems encountered in the management of the maintenance operations such as provision of as-built drawings; working space and safe access to defective portions; choice of correct construction materials and methods by certified personnel were not taken care of during the design stage. The study recommended that all building items, elements or components be designed and constructed for ease-of-maintenance to ensure better future performances.