This paper introduces some studies developed regarding the Medicea Villa at Poggio a Caiano, in Italy. The monumental building was built by Lorenzo de’ Medici and his heirs following the design of the famous architect Giuliano da Sangallo, between 1485 and 1520. The Villa embodies many of the typical features of the Italian Renaissance, added a monumental double circular stairway in the front façade during neoclassical times, heading to the upper balcony surrounded by a balustrade. The Villa was surveyed taking advantage of Terrestrial Laser Scanning and Digital Photogrammetry, in order to produce a detailed model to be translated into a HBIM digital prototype then. The Scan-to-BIM approach was obtained with a generation of semantics and components proper of Sangallo’s architectural grammar, first of all defining the object, then geometry, and then their parametrization. This process led to a model of the exteriors, used to better understand the architectural composition of the volumes, to make some hypothesis on its shape according to the original architect’s drawing in the Taccuino Senese, on its general structural behaviours, to understand the limits of a process and the perspective of a research that goes from a digital survey to the HBIM environment.