This chapter argues that the increasing rate of commercial and location-specific transactions conducted in Jerusalem from the 1130s reflects the gradual densification of the settlement in Jerusalem and the emergence of a proto real estate market. This process occurred simultaneously with, or even preceded, Jerusalem’s monumental transformation. This approach challenges previous notions concerning the periodisation, underlying causes and scope of the city’s transformation. The chapter also traces the development of residential areas and analyses the different strategies employed by Jerusalem’s institutions in their municipal policies. It argues that from the middle of the twelfth century a shift occurred in the balance between the different institutions that were engaged in the urban sphere, which led to changes in patterns of property ownership and to the development of new areas. In doing so, this chapter also sheds new light on the connection between the city’s devotional and monumental space and its residential/commercial development.