Urban streets are public spaces that can gather residents and create vibrant and diverse experiences contributing to the positive qualities of an urban landscape. Windhoek’s suburban model, which has evolved from colonial and apartheid planning, relies heavily on private motorcars, which most residents cannot afford. The city’s various neighbourhoods have historically been segregated by race, ethnic group, and wealth. The city lacks public spaces where different residents can easily and freely interact. Windhoek presents a particularly unsettling disconnect between the formal systems governing and producing the city and residents' socio-cultural backgrounds and everyday spatial practices. Windhoek presents a particularly unsettling disconnect between the formal systems governing and producing the city and residents' socio-cultural backgrounds and everyday spatial practices. This paper develops a methodology that combines non-expert participatory methods and tools to investigate perceptions of young residents of Windhoek’s streetscape, extending beyond objective spatial descriptions and generalised socio-political critiques to address individual subjective perceptions, recollections, and experiences of specific urban spaces within Windhoek. The conceptual lens of the uncanny is employed as an organising concept to consider how the spatial and social legacies of colonialism and apartheid continue to affect Windhoek residents’ perceptions and behaviours in publicly-accessible spaces. The paper examines residents’ objective topological understandings of the city’s spatial structure, their movement through it, and their subjective, qualitative social perceptions about place, value and belonging connected to that spatial understanding.