Buildings and other infrastructure in urban areas around the world are responsible for a significant portion of local and global impacts of energy use and climate change. The incorporation of sustainable and renewable technologies such as the use of sustainable building material, photovoltaic systems or solar thermal systems on building rooftops is being widely investigated and applied. Urban planners and policy makers generally need to select from many existing optimized solutions for urban scale applications of sustainable and renewable technologies. The benefits of different types of sustainable technology vary greatly depending on geographical location, weather, and available resources and technology. For these reasons, the optimization of sustainable technology needs to be incorporated as part of the critical decision-making process. Although direct and indirect benefits of one technology for an individual building can be relatively easy to assess, as yet there is little understanding of the potential benefits of combined and optimized implementation of such systems. This study reports the development of a hierarchical methodology for assessing the optimized capacity and benefits of multiple sustainable and renewable technologies in an urbanized area. The proposed method is a holistic approach which incorporates energy generation and the savings potential of two different technologies as well as life cycle costing which integrates both the capital cost of each system and the monetary value of environmental impact mitigation. The results of this study will provide a new approach to technology optimization in support of sustainable urban development.