A process of land squandering began in Spain in the mid 1990s until the great crisis of 2008. The intensive production of urban land affected the Spanish medium-sized towns. They were characterized by their compact nature and then they underwent an intense diffuse urbanization. However, in some cases there had been previous examples of urban sprawl. In this article, we study one of them, the unique and historic city of Toledo, in the Centre of the Iberian Peninsula. We will show how the city has experienced the land squandering and has been extensively widespread throughout the hinterland, consisting of their peripheral municipalities. We will also check how Toledo has had a previous internal dispersion process in the last quarter of the 20th Century through the called Ensanche (widening). We will use the urban estate cadaster as a fundamental source for evolutionary and present analysis of the city and its hinterland. The field and bibliographic work complete the methodology. The final conclusion is that there have been remarkable urban increments in Spanish medium-sized cities such as Toledo, in external and peripheral districts, under the logic of speculation and profit, resulting in a disjointed space.2 of 17 cities are characterized by the role played in the territory not only regarding the capacity to articulate their environment but also regarding the influence that they generate and the relationships that they are able to establish with other spaces. In short, it must be highlighted their role as carriers of goods and services to those cities and/ or rural municipalities on which they exert influence. In addition, their ability to connect different levels of networks (at a local, national, and even international level) is remarkable [9].The definition of intermediate cities with their clear vocation of intermediation, left the quantitative criteria behind to conceptualize from the explanation of qualitative, economic, functional and territorial factors, where the capacity to organize more balanced urban systems with a higher quality of life is essential [10].The most recent studies on medium-sized cities have been approached from different perspectives (scattered and oversized growths-in most cases-which leave the traditional compact city model aside) that share one thing in common: the model of diffuse city. However, the term is not subject to a concise definition. On the contrary, and it is the same as with the concept of medium-sized cities, this reality associated with urban sprawl does not have a clear definition since their building density, the morphological typologies, the intensity of use and/or the possible territorial effects to which urban dispersion refers are unknown [11].This phenomenon has been characterized from different terms that come to represent a similar reality: city-region [12], urbanized field [13], diffuse city model [14], city sprawl [15], no city [16], inefficient city [17]. The explanatory processes that derive in this situation are also complex and are hidden under vague ter...