The contribution integrates historical readings, conducted through archive documents and iconographic materials, with surveys and graphical analyzes carried out through direct knowledge of Palmariggi’s historic center in Salento. The imposing Aragonese castle of which today only the two cylindrical towers remain, joined together by a stretch of perimeter masonry, initially presented a quadrangular plan with four corner towers, of which three are cylindrical and one is square and was surrounded by an existing moat, until the middle of the twentieth century, with a wooden drawbridge on the eastern side. The fortress was part of a strategic defensive system, designed to protect the village and the productive Otranto’s land with which it was related. The fortified Palmeriggi’s center represented an important defensive bulwark placed within the network of routes and agricultural activities that led from the hinterland to the port of Otranto, where flourishing trade took place. The research examines the changes undergone by the defensive structure that has had several adaptations made initially in relation to changing military requirements, resulting from the use of firearms, the upgrades that were supposed to curb the repeated looting and the military reprisals against the inhabited coastal and inland centers of Salento peninsula, and later social that led to the expansion of fortified village with Palazzo Vernazza’s (eighteenth century) adjacent construction and the original parade ground’s elimination. Summing up, the contribution in addition to documenting the current situation with integrated surveys, the state of preservation of fortified structure with its village, of which it examines the urban evolution based on the construction, typological and morphological systems, relates to the surrounding territory by comparing the plant of the ancient nucleus with that of neighboring fortified Salento’s centers. Finally, digital study models allow fortified structure’s three-dimensional analysis, its construction techniques, assuming the original shape.