In an era of rapid urbanization, the convergence of population expansion and urban development has spawned challenges, notably the heightened threat of flooding and consequential economic losses. Pronounced in densely urbanized areas, where impermeable surfaces and modified hydrological systems intensify flooding impacts, understanding the intricate dynamics between urbanization, flooding, and economic loss has become a central focus. Economic implications have been probed extensively, with studies advocating proactive investments in infrastructure and disaster preparedness for enhanced economic resilience. Globally, flooding in coastal regions has emerged as a significant concern. The complex interplay of urbanization, flooding dynamics, and economic losses in the upper East Galveston Bay is analyzed for a 100-year storm frequency from 2001 to 2019, focusing on flooded structures and economic losses. The study discerns an 8% increase in flooded structures, indicating susceptibility, with a plateau during 2011 to 2016. Economic losses, comprehensively assessed through the GO-Consequence model, exhibit a progressive increase from 2001 to 2019, underscoring the urgency for proactive flood mitigation. Differential impacts on structure types highlight the necessity for tailored urban planning. The temporal analysis signals a concerning susceptibility to flooding, emphasizing the need for holistic mitigation strategies, contributing to ongoing discourse on resilient urban planning.