In the Global South, cities are increasingly restructuring themselves around the financial pressures of international capital markets. Therefore, it is sometimes hypothesised that financial innovations created in the Global North are moving ‘South’. However, even though transnational capital is finding its way into Southern regions and other areas of reform, the road towards urban commodification is bumpy and uneven. In Havana, Cuba, the government recently legalised free market home sales, contributing to an unprecedented transnational property boom where many homes were acquired by Cuban émigrés and nationals and converted into restaurants, hotels or short-term rentals. Nevertheless, due to endogenous and exogenous market restraints, the pandemic and complex interactions between state authorities and property-owning private entrepreneurs, Cuban-style commodification remains an incomplete and contested process. Even so, non-debt bearing assetisation pressures are clearly redefining Havana’s socialist property market. While the state encourages foreign direct investment into state-owned hotels and joint ventures, transnational remittances contribute to the commodification of Havana’s private housing stock.