This article contends that envisioning the future of housing planning in post-socialist cities necessitates the acknowledgment of a pressing reality: Many societies are undergoing rapid aging and depopulation. Latvia’s capital city of Riga, the focal point of this study, stands at the forefront of these global trends. However, due to entrenched neoliberal practices that idealize youthful, robust, and entrepreneurial residents, considerations of aging are conspicuously absent from urban planning visions. Drawing on ethnographic research conducted in the capital city between 2021 and 2023, this article establishes a link between urban lived experiences while aging and the intersecting dynamics of housing. The critical analysis is informed by data derived from observations, conversations, media sources, official discourses, and perspectives gathered through expert interviews. Ultimately, this article advances an agenda aimed at urging people to think about more hopeful futures for aging in cities, an issue of paramount significance in the post-socialist societies of the 21st century.