Abstract. The paper presents a novel adaptive parametric documentation, modelling and sharing methodology, which aims to achieve a continuous holistic documentation, data processing and sharing process for cultural heritage community, such as architects, engineers, archaeologists, conservators, programmers, fabricators, contest creators, game developers, scholars and common citizens. Thus, the use of advance parametric and building information modelling software allows the processing and specification of all data by creating the 3D models needed for the multidisciplinary experts. Two Cypriot case studies from the medieval time period have been chosen for the development, and evaluation of our proposed methodology in order to investigate the process of modelling and sharing all the given metadata and 3D data. The first one is the Asinou Church, a UNESCO Heritage stone monument in the Troodos Mountains with a unique interior and the Kolossi Castle, a former Crusader stronghold on the west of the city of Limassol on the island of Cyprus.