Despite their very different political and economic contexts, both Luanda and Nairobi have experienced housing booms and urban property bubbles over the last fifteen years. Both also exhibit the “extreme splintered urbanism” found in other urban landscapes across Africa, where sprawling informal settlements with inadequate housing and services border new middle class suburbs. This study relies on a most different systems design to identify the common drivers of urban transformation and housing provision in Luanda and Nairobi. It argues that three intersecting features explain similar patterns and outcomes in these two capital cities: aspirations for home ownership by urban residents; the reliance by governments on the delivery of goods (including housing) to gain political support and legitimacy; and the aggressive competition by private and public sector actors to gain housing contracts and promote mortgage markets. The study employs archival research from four countries; household surveys, site visits, and interviews; and geocoded data on gated communities and satellite cities in Luanda and Nairobi to compare the processes of urban growth in the two cities. Its findings on the political economy of housing provision and market development will offer insights into similar processes occurring across the African continent.