This paper has traced the historic spatial development of Windhoek through five distinct socio-political epochs. These different periods’ spatial, aesthetic, and representational effects on the city’s urban landscape are presented in original maps, allowing a spatial-to-scale comparison and analysis of the city’s development. Rather than the discrete chapters in Windhoek’s urban development, successive occupations’ spatial compositions are shown to have been assembled from and grounded in the geomorphological, spatial, social, and administrative conditions preceding them. The paper expands the concept of the uncanny, the colonial drive to recreate home in foreign lands and local resistance to this, from the architectural to the urban. It describes how infrastructure, residential typologies and neighbourhood morphologies, memorials, places of memory, and public space were designed to segregate and subjugate Windhoek’s population and how this spatial legacy continues to inform city-making in Windhoek today. In doing so, the paper challenges the notion that the city’s spatial structure, layout, and urban planning are neutral quantitative entities.