The implementation of condition monitoring for damage identification and the generation of a reliable digital twin are essential elements of preventive conservation. The application of this promising approach to Cultural Heritage (CH) sites is deemed truly beneficial, constituting a minimally invasive mitigation strategy and a cost-effective decision-making tool. In this light, the present work focuses on establishing an informative virtual model as a platform for the conservation of the monastery of Santa Maria de Salzedas, a CH building located in the north of Portugal. The platform is the first step towards the generation of the digital twin and is populated with existing documentation as well as new information collected within the scope of an inspection and diagnosis programme. At this stage, the virtual model encompasses the main cloister, whose structural condition and safety raised concerns in the past and required the implementation of urgent remedial measures. In the definition of a vibration-based condition monitoring strategy for the south wing of the cloister, five modes were identified by carrying out an extensive dynamic identification. Nonetheless, significant challenges emerged due to the low amplitude of the ambient-induced vibrations and the intrusiveness of the activities. To this end, a data-driven Optimal Sensor Placement (OSP) approach was followed, testing and comparing five heuristic methods to define a good trade-off between the number of sensors and the quality of the collected information. The results showed that these algorithms for OSP allow the selection of sensor locations with good signal strength.