Assessing the quality of urban street space can provide suggestions for urban planning and construction management. Big data collection and machine learning provide more efficient evaluation methods than traditional survey methods. This study intended to quantify the urban street spatial quality based on street view image segmentation. A case study was conducted in the Second Ring Road of Changsha City, China. Firstly, the road network information was obtained through OpenStreetMap, and the longitude and latitude of the observation points were obtained using ArcGIS 10.2 software. Then, corresponding street view images of the observation points were obtained from Baidu Maps, and a semantic segmentation software was used to obtain the pixel occupancy ratio of 150 land cover categories in each image. This study selected six evaluation indicators to assess the street space quality, including the sky visibility index, green visual index, interface enclosure index, public–facility convenience index, traffic recognition, and motorization degree. Through statistical analysis of objects related to each evaluation indicator, scores of each evaluation indicator for observation points were obtained. The scores of each indicator are mapped onto the map in ArcGIS for data visualization and analysis. The final value of street space quality was obtained by weighing each indicator score according to the selected weight, achieving qualitative research on street space quality. The results showed that the street space quality in the downtown area of Changsha is relatively high. Still, the level of green visual index, interface enclosure, public–facility convenience index, and motorization degree is relatively low. In the commercial area east of the river, improvements are needed in pedestrian perception. In other areas, enhancements are required in community public facilities and traffic signage.