Abstract This paper critically reviews the role of performance-based generative design in fast prototyping of buildings, describes the methodology of an automated generative layout design to produce complete building solutions, and presents a case study of multi-story buildings in urban context. The proposed approach evolves the building design solutions by interacting with the city 3D geometry and evaluates the energy consumption for air-conditioning. The building designs take into consideration urban geometric constraints and objectives, such as alignment with surrounding buildings, urban lot area, and relative and absolute position of the generated elements. During the evaluation process, the urban context is considered for casting shadows and reflecting solar radiation. The case study consists of six alternative 15-story buildings located in the city of Sao Paulo (Brazil), having commercial areas on the ground floor and two apartments per story on the remaining floors. The results show that, despite having similar apartments in every story, the urban context has a relevant impact on the buildings' energy performance. The difference between the apartments' best and worst energy performing stories ranges from 9% to 12% (ignoring the outlier story located in the first level), depending on the building solution. The results also show that the most energy efficient apartments’ story is not located in the top or bottom floors, but rather at an intermediate level.