In the continental Mediterranean mountains of the Iberian Peninsula is located a landscape characterized by the presence of enclosed land parcels delimited by dry stone walls or vegetation, or by both these elements. This landscape has been included, since 2018, in UNESCO’s Representative List of Intangible Cultural Heritage of Humanity under the name of Art of dry stone walling, knowledge and techniques. However, today’s territorial dynamics jeopardize the maintenance of this landscape heritage. This work set out to understand their origins, dynamics, and evolution from the 11th century (Middle Ages) to the present using historical documentation from different sources and diachronic cartography from aerial photographs. The fieldwork was designed to identify natural, cultural features and recent dynamics, in particular those related to urbanization changes of the last 70 years. Finally, we delved into the new dynamics of exploitation that were based on extensification and a loss of productive diversity. The results obtained lead us to consider that the loss of this agro-landscape must be prevented, with a reasonable livestock grazing criteria and a rational management of its heritage features. This requires regional, national, and European policies that recognize the enclosed landscape as a heritage ecosystem in which biodiversity and agriculture are closely linked.