Recently, deep learning techniques, specifically semantic segmentation, have been employed to extract visual features from street images, a dimension that has received limited attention in the investigation of the connection between subjective and objective road environment perception. This study is dedicated to exploring and comprehending the factors influencing commuters’ perceptions of the road environment, with the aim of bridging the gap in interpreting environmental quality in Thailand. Semantic segmentation was applied to identify visual objects, expressed as a percentage of pixels represented in 14,812 street images from the Bangkok Metropolitan Region. Subjective road environment perception was assessed through a questionnaire, with a total of 3600 samples collected. Both sets of data were converted to average values per grid, with a grid size of 500 × 500 square meters, resulting in a total of 631 grids with data points. Finally, a multiple linear regression model was employed to analyze the relationship between the ratios of objects obtained from street images via semantic segmentation and human sensory perception of the road environment. The findings from this analysis indicate that the attributes of distinct object classes have a notable impact on individuals’ perceptions of the road environment. Visual elements such as infrastructure, construction, nature, and vehicles were identified as influential factors in shaping the perception of the road environment. However, human and object features did not exhibit statistical significance in this regard. Furthermore, when examining different road environments, which can be categorized into urban, community, and rural contexts, it becomes evident that these contexts distinctly affect the perceptions of various road environments. Consequently, gaining a comprehensive understanding of how street environments are perceived is crucial for the design and planning of neighborhoods and urban communities, facilitating the creation of safer and more enjoyable living environments.