Ioannina, a city in northwestern Greece, has undergone a long Byzantine and Post-Byzantine/Ottoman period, thus having acquired a multicultural profile clearly depicted in architectural assets of the urban web. Unfortunately, most of the landmark buildings have been destroyed, often having left little or no trace at all in situ. Nevertheless, it is still possible to detect the dating and form of those demolished, but cited in literary sources, making also use of architectural typology. Crosschecking with geospatial data and related optical depictions, can further clarify and enhance the research procedure. In a consequent stage of work, the research results, as afore-mentioned, can constitute the starting point for digitally 3D reconstructing the building under question. Given the fragmentary basis of the information available, and concerning the present case-study, the 3D digital approach should be abstractive, outlining the basic architectural elements as well as the dimensions of the structures under question. Conclusively, digital building archaeology can contribute creatively to the exploration of the urban fabric and the evolution of the urban landscape over time, as well as to the dialogue of a building with the urban web. The cultural palimpsest of the south-eastern Citadel of Ioannina Castle, as deployed in two Byzantine Christian Cathedrals, a Muslim Mosque and their respective tombs, as well as in an Ottoman administration building complex, constitutes the case-study of the post-doctoral research project’s related chapter as briefly outlined.