To make safe road-crossing decisions, it is necessary for pedestrians to accurately estimate the speed and stopping distance of approaching vehicles. Accordingly, the objective of our study was to examine the effects of multiple factors, such as weather conditions, context time (day or night), and illuminance of the roads, on older pedestrians’ (>60 years old) speed perception and stopping distance estimation of approaching vehicles. The participants in this study included 48 older participants who were asked to estimate the speed and stopping distance of approaching vehicles based on 12 s video clips that were selected from natural conditions. The results revealed that actual speeds, weather, context time, and lighting conditions played important roles in the performance of the participants. Compared with young adults, older pedestrians were found to have smaller accurate estimation intervals that varied by multidimensional influencing factors and thus resulted in missing road-crossing opportunities at lower vehicles’ speeds and increasing road-crossing dangers at higher speeds. The older pedestrians’ performance with respect to speed perception and stopping distance estimation is modeled using a regression model with a complex level of tasks. These models can be used by engineers when establishing speed limits and lighting conditions in the areas with senior residents.