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Typical Meteorological Year (TMY) datasets, widely used in building energy modeling, overlook Urban Heat Island (UHI) effects and future climate trends by relying on long-term data from rural stations such as airports. This study addresses this limitation by integrating Urban Weather Generator (UWG) simulations with CCWorldWeatherGen projections to produce microclimate-adjusted and future weather scenarios. These datasets were then incorporated into an Urban Building Energy Modeling (UBEM) framework using Urban Modeling Interface (UMI) to evaluate energy performance across a low-income residential neighborhood in Des Moines, Iowa. Results show that UHI intensity will rise from an annual average of 0.55 °C under current conditions to 0.60 °C by 2050 and 0.63 °C by 2080, with peak intensities in summer. The UHI elevates cooling Energy Use Intensity (EUI) by 7% today, with projections indicating a sharp increase—91% by 2050 and 154% by 2080. The UHI will further amplify cooling demand by 2.3% and 6.2% in 2050 and 2080, respectively. Conversely, heating EUI will decline by 20.0% by 2050 and 40.1% by 2080, with the UHI slightly reducing heating demand. Insulation mitigates cooling loads but becomes less effective for heating demand over time. These findings highlight the need for climate-adaptive policies, building retrofits, and UHI mitigation to manage future cooling demand.