Local administrators and private investors rely on various urban redevelopment strategies, the choice of which depends on the economic expectations of property owners and investors. Some of these options foresee replacing obsolete buildings with new constructions; others prefer the reuse of existing assets. This study examines the conditions that make these different strategies feasible, bringing to light the aspects that favor demolition and reconstruction processes over interventions based on the redevelopment of existing assets. The analysis focuses on the variables that determine the choice between these two options. The model that has been developed highlights, on one hand, the role of urban planning tools and urban densification and, on the other, the relationship between the land market and the value of existing assets. The model has been tested on five cities in northern Italy, which fall into three territorial categories—large metropolitan cities, medium-sized cities, and cities of limited rank—to test how different social and economic contexts affect the feasibility of the strategies we evaluated. The results of the study underscore the extent to which the demolition and reconstruction of existing assets is only viable in certain limited areas and under particular market and settlement conditions. While large metropolitan areas seem to have the option of radically replacing existing real estate assets, medium-sized cities and especially small cities are constrained in redeveloping existing urban assets and must forego demolition and reconstruction projects, which do not prove to be economically feasible.