||Artificial light has transformed urban life, enhancing visibility, aesthetics, and increasing safety in public areas. However, too much unwanted artificial light leads to light pollution, which has a negative effect on public health and urban ecosystems, as well as on the aesthetic and cultural meanings of the night sky. Some of the factors interfering with the estimation of light pollution in cities are urban features, such as the presence of trees, road dimensions, and the physical characteristics of buildings. In this study, we proposed a simplified model for unwanted upward light coming from street luminaires based on a building height model and the publicly accessible Google Street View images. We simulated and analyzed the obstruction effects of different street features on the light pollution caused by the street lighting system in Cambridge, Massachusetts. By providing quantitative information about the connections between the streetscape features and the amount of unwanted upward artificial light, this study provides reference values to inform policies aimed at curbing light pollution.