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Urbanization and climate change have intensified the need for advanced methods to simulate building energy performance within realistic urban environmental contexts. This study presents a microclimate-informed framework for developing representative building energy prototypes that enable the estimation of energy use for buildings sharing similar microclimatic conditions and building-level characteristics. The framework is demonstrated using Des Moines, Iowa, as a case study. The framework combines high-resolution microclimate modeling with geospatial analysis to quantify the influence of urban form and vegetation on building energy use. Localized weather files were generated using the Weather Research and Forecasting (WRF) model to capture spatial variations in microclimate across the city. Detailed three-dimensional models of buildings and trees were developed from Light Detection and Ranging (LiDAR) point cloud data and integrated with building attributes, including construction materials and heating and cooling systems, to generate representative building typologies use them to build a similarity-based lookup table. Urban energy simulations were conducted using the Urban Modeling Interface (UMI). To demonstrate the effectiveness of the framework, simulations were conducted for two building prototypes according to the framework. Results show that monthly energy use intensity (EUI) of a representative cluster compared to randomly selected buildings differs by 10% to 19%, with both positive and negative deviations observed depending on building template and month. Thus, the proposed framework shows great promise to capture comparable energy performance trends across buildings with similar construction characteristics and urban context and minimize computational demands for doing so. While evapotranspiration effects are not explicitly modeled in the current framework, they are recognized as an important microclimatic process and will be incorporated in future work. This study demonstrates that the proposed framework provides a scalable and computationally efficient approach for urban-scale energy analysis and can support data driven decision making for climate-responsive urban planning.