Much contemporary economic growth in Africa is driven by urban service sectors including construction and real estate. This manifests in rapidly transforming landscapes and the proliferation of valuable property in the continent’s booming large cities, often accompanied by growing socio-economic inequality. In this context, improving systems for property taxation is an urgent and growing need – something that national and international policymakers increasingly recognise. Despite this, even in states considered particularly ‘developmental’ and committed to increasing tax revenue, property taxation has fallen by the wayside. This paper argues that, in addition to the usual technical and political difficulties associated with property taxation, it is crucial in reform-oriented developing countries to understand the nature of land tenure systems and how they are changing, as well as historical legacies relating to land and housing. Moves to introduce or improve property taxation need also to be considered in relation to how contemporary development strategies constrain or facilitate investment in real estate, and the political economy underpinning this sector. Through an analysis of existing property tax and land leasing systems in Kigali and Addis Ababa, as well as failed, stalled and ongoing reform attempts in each, the paper identifies key themes for the study of property taxation systems and their potential to succeed in rapidly transforming cities in the global South.