From the beginning of the twentieth century, new urban housing forms, including social housing, land pooling, and building syndicates, began to emerge as products of housing rights and labor movements. Yet this emergence cannot simply be accounted for by a history of workers' rights and housing movements but must also take into consideration the political economy of land and housing created by new forms of real estate speculation. This article situates the history of urban speculation and the new fiduciary innovations pertaining to urban land and housing markets within the scholarship on the development of architectural and town-planning theories during the early decades of the twentieth century. Focusing on Calcutta and Bombay—two central cities of the British Empire—as case studies, I will trace the history of how the housing market became a tradeable object of speculation through colonial policies that disentangled housing from its singular history and abstracted it out of its nonmonetizable attachments. Indeed, it is by understanding how the land and housing market became a site for future investments and ultimately was structured through new social relations and values following World War I that we might get a fuller understanding of how we arrived at our contemporary “residential capitalism” and landscapes of accumulation and homelessness.