This study examines how senior residents navigate the overlapping logics of dispossession and re-possession within urban redevelopment, situating this dialectic within the broader framework of spatial commodification and lived spatiotemporal experiences. While urban redevelopment offers compensation and improved housing, it also generates deep emotional, functional, and temporal disruptions – particularly for older adults. Spatially, redevelopment projects prioritise abstract commodified space, often disregarding seniors’ affective and symbolic attachments to their neighbourhoods. Importantly, seniors’ attachments to place are not uniformly positive. Many express frustrations with deteriorating environments and social fragmentation, viewing redevelopment as an opportunity to improve living conditions or family wealth accumulation. The tension between loss and gain – between being dispossessed and being re-possessed – shapes their complex responses to displacement. These dynamics are further complicated by the temporal mismatch between institutional redevelopment timelines and seniors’ embodied rhythms, such as ageing-related limitations, care responsibilities, and uncertainty about future arrangements. Meanwhile, shifting intergenerational dynamics within the family domain reveal that even with financial compensation and increased family wealth, conflicts often emerge around caregiving and benefits distribution. By centring these tensions, this study moves beyond binary accounts of victimhood or compliance and highlights the ambivalence and contingency in seniors’ engagement with redevelopment. It calls for more nuanced policy responses that align material compensation with emotional and temporal needs, particularly in contexts where family-based ageing care remains central.