Abstract Until the 17th century, the Dutch coastal region of Zeeland ranked among Europe's most urbanized areas, driven by thriving international trade networks. People living in this time of flourishing economy benefitted enormously from it in terms of employment opportunities and working conditions, which were reportedly better than in the rest of the Low Countries. However, the rapid growth of Zeeland's urban centers likely presented increasing challenges for the population in terms of accessing essential resources, including food, clean water, and housing. In the 19th century, Zeeland's economy ultimately faced a significant downturn due to the decline in the maritime trade, leading to a substantial reduction in its urban population. Examining patterns of urbanization and economic histories that differ from the commonly studied thriving industrial contexts in bioarcheological research, as exemplified by Zeeland, is a crucial yet relatively underexplored facet in our efforts to understanding the human past. To address this gap, this study investigates the impact of urbanization on the health of Zeeland's inhabitants over time by analyzing nonspecific stress markers (i.e., cribra orbitalia, porotic hyperostosis, and linear enamel hypoplasia) and chronic maxillary sinusitis in a sample of 246 individuals from three urban sites dating from 1030 to 1800 CE. Our analysis of skeletal remains reveals significant differences in the prevalence of porotic hyperostosis, linear enamel hypoplasia, and sinusitis between the medieval and post‐medieval periods. These findings suggest that de‐urbanization and economic decline adversely affected the health and well‐being of the populations under study, influenced by factors such as working conditions and food availability. This study provides a new perspective on bioarcheological approaches to urbanization, shedding light on the intricate realities of urbanization in Zeeland and offering important insights into its complexities.