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A relationship of building space conditioning energy and density of built-up area using street geometry as an urban design parameter was investigated in this study. Sixteen street geometry configurations with varying street width and orientation were investigated. A comparative energy analysis of a single, stand-alone eight-storey office building, with the same building as a part of urban building configuration, is presented. The sensitivity of microclimatic changes of increased air temperature and reduced wind speed was investigated for the building energy need of a compact street geometry. Additionally, the role of improved wall and roof surface albedo values on energy needs was studied in the urban context. The street geometry significantly influences the space conditioning energy of an urban building. The summertime cooling load of a code rated energy efficient building is reduced by up to 37% whereas heating loads are penalized by 19% by the studied street aspect ratio of 8. However, microclimatic influences can reduce cooling energy savings by up to 8% and reduce heating energy penalty by 15% for the Chicago climate. High cooling load reduction by a high street aspect ratio is synonymous with high achievable density of the built-up area, but blocked daylight access increases the need for artificial lights. In summary, higher street aspect ratio represents a compact development and promises higher annual cooling energy savings; however, selection of environment- and development-friendly street geometry remains a compromise for energy efficient building.