AbstractHousing supply is a controversial topic across the globe. In Europe, for example, housing provision is fundamentally characterised by capitalist market economy. However, the intensity of state intervention differs significantly in the respective European countries. Germany is certainly one of the countries in which the state traditionally intervenes considerably in the housing market and attempts to control it through various measures. In addition, the stakeholders in the housing market are very different, and the housing market is highly segmented. In Cuba, as a rather atypical example for Latin America, where the housing market is largely liberalised, the housing market is very strongly regulated by the socialist Cuban state. In this article, we address the topics of housing supply by analysing the institutional framework conditions and the different levels of intervention in the very different systems of Germany and Cuba. In doing so, we find that the objectives at the planning and political levels in these two case studies are quite similar despite the major political and social differences. It has become clear, that there is a gap between the aspiration of the political-administrative planning system and the planning expectations of the citizens in both systems. However, it is also emphasised that the state's claim to intervene in the housing market and the regulations, production and financing conditions are very different. Using Vaus’s ‘most-different-case approach’, we emphasise for the two cities of Hamburg and Havana that although considerable successes have been achieved in both systems in terms of adequate housing provision, but major challenges still exist in both cities. The analysis has also made clear how important it is to combine housing policy demands with the realities of housing industry, real estate markets and urban planning perspectives.