The contribution intends to analyse, by comparing documentary sources and material reality, the processes of decastellation that occurred between the 13th and 14th centuries in a territory immediately outside the city walls of Florence. The castles present in this part of the contado, attested between the 11th and 12th centuries, suffered late abandonment only on rare occasions; in all other cases, on the contrary, there was an early process of decastellation that, already in the second half of the 13th century, led to the birth of “new” forms of living (case da signore, tower houses, palagi, forts) that took up residence on the ancient castles, at the same time as the new mercantile elite of the city (Peruzzi, Bardi) took over these sites. The rural lordly residences that arose on the ancient castles, studied through an archaeological analysis of the architecture, will be compared with iconographic and written sources, in order to identify the signs of a phenomenon that during the 14th century transformed the Tuscan countryside close to the city, generating “new” types of extra-urban residences.