The hyper mobility of capital and the associated growth of international investment in real estate which occurred across the world in the late twentieth century, led to bursts of property development and market booms. This article examines how this global trend interfaced with local processes in the setting of a secondary metropolis of a developing country, in Metro Cebu, Philippines, and resulted in a property-led development dominated by production of high-end residential real estate commodities, the rise of a speculative land market, and a highly regressive spatial allocation. It is argued that this regressive outcome was mediated by a weak state, controlled and dominated by predatory and rent-seeking bosses who, in Cebu in particular, are not simply representatives of the local oligarchy but are big real estate developers and brokers themselves. During the boom period, neither the middle classes, whose members were also attracted to speculative property buying, nor the low-income and urban poor groups, who were largely hoodwinked by official rhetoric of social housing reform and by token participation, provided any significant social force to constrain the opportunism and rent-seeking of these bosses or to challenge the pro-growth governing agenda.