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Increased urbanization and climate change have resulted in the intensification of the urban heat island (UHI) effect, particularly in tropical cities. One of the main causes of UHI is the man-made urban surfaces influencing the radiation budget by absorbing, reflecting, and emitting radiation at various wavelengths. The radiative budget of a city is directly influenced by the urban geometry, surface materials, direct solar radiation and incident angle, and atmospheric diffuse radiation. Vegetation cover, in contrast, can decrease UHI by intercepting radiation and through the process of photosynthesis. Better understanding the effect of urban vegetation on the radiative budget can thus contribute towards the mitigation of the UHI effect and ultimately the development of climate resilient urban spaces. To analyze the contribution of vegetation to the radiative budget of a city, a detailed simulation of the complex interaction between the built environment and the vegetation is required. This study proposes an approach for analyzing the 3-D structure of both vegetation and built environment to quantify the contribution of vegetation to the radiative budget of an urban landscape. In a first step, a detailed 3-D model of Singapore including buildings and vegetation was reconstructed using a combination of free and commercial Earth Observation data. Then, the 3-D Discrete Anisotropic Radiative Transfer (DART) model was repurposed to estimate the radiation absorbed by the urban surfaces accounting for the presence of vegetation cover with changing Leaf Area Density (LAD) conditions. The presence of trees in the scene accounted for a significant reduction of the absorbed radiation by buildings and ground. For example, in the case of a residential low-building neighborhood, although having low tree cover, the reduction of the absorbed radiation by buildings and ground was up to 15.5% for a LAD =1. The field validation shows good agreement (R-2 = 0.9633, RMSE = 10.8830 and Bias = -1.3826) between the DART-simulated shortwave exitance and upwelling shortwave measurements obtained from a net radiometer mounted on a local flux tower in the urban area of Singapore, over the studied period. Our approach can be used for neighborhood-scale analysis, at any desired location of a city, to allow test scenarios with varying surface materials and vegetation properties.