Urban growth is increasingly shifting from horizontal expansion to vertical development, resulting in skylines dominated by high-rise buildings. The post-construction operations and maintenance of these buildings are critical, requiring regular structural health monitoring (SHM) to proactively identify and address potential safety concerns. Interferometric synthetic aperture radar (InSAR) has proven effective for monitoring building safety, but most studies rely on high-resolution synthetic aperture radar (SAR) images. The high cost and limited coverage of these images restrict their use for large-scale monitoring. Sentinel-1 medium-resolution SAR images, which are freely available and offer broad coverage, make large-scale SHM more feasible. However, studies on the use of Sentinel-1 SAR images for structural health monitoring, especially at large spatial scales, remain limited. To address this gap, in this study, Sentinel-1 SAR images and PS-InSAR technology are proposed for performing a comprehensive structural safety assessment of super high-rise buildings in the Guangzhou–Foshan Metropolitan Area (GFMA) and for analyzing the influencing factors. Our assessment shows that while the overall structural safety of these buildings is satisfactory, certain areas, including Pearl River New Town, central Huadu district in Guangzhou, and southeastern Shunde district in Foshan, exhibit suboptimal safety conditions. We verified these findings using GNSS data and on-site investigations, confirming that Sentinel-1 SAR imagery offers reliable accuracy for monitoring building structural health. Furthermore, we identified factors such as settlement in soft soil layers, the construction of surrounding (underground) infrastructure, and building aging, which could potentially impact building structural safety. The results demonstrate that Sentinel-1 SAR images provide a reliable, rapid, and cost-effective method for the large-scale monitoring of building stability, enhancing our understanding of the underlying mechanisms and informing strategies to prevent potential safety crises, and also ensuring the sustainable development of society.