Despite the growing recognition that metropolitan real estate markets are segmented spatially and that property development is still profoundly local, research has taken little notice of agents that actually initiate and propel the development process. Earlier studies that aimed at identifying metropolitan segmentation employed statistical techniques whilst ignoring the practices of agents that might shed light on the notion of segmentation. Greater Toronto’s office market, which is Canada’s largest, exemplifies a real estate market far more spatially segmented than the downtown–suburban framework, a dichotomy so extensively use in research. Locational preferences of the numerous developers that work in this market tend to be highly localized, confirming deep-rooted segmentation. Their preferences correspond to submarket classification and follow dividing lines that crisscross the metropolitan region, emphasizing the extent and the power of parochialism, which defines the nature of real estate development.