The paper presents a study on the dredging vibrational effects, for nourishment purpose, on the existing structures surrounding the worksite. Nourishment is a common operation when beach (or coasts, or ports) protection is required, allowing to reduce far-field impacts of coastal structures and improve navigability. Nourishment is then performed to reshape underwater land, and it is usually practiced by locating in the zones in which is required, soil coming from nearby areas. This latter is often obtained by a dredging process, in which the phases of excavation, transportation and soil placement are carried out. From the structural point of view, of interest is the excavation phase, which is usually performed in the water environment by a ship equipped with a dredge that mines the seabed, generating a new source of vibrations for the existing structures facing the working area. The aim of this paper is to assess the effects of vibrations induced by dredging operations, by taking as reference the recently performed nourishment in the port of Bari, Southern Italy. To this scope, an existing structure was selected and identified as sentry building, considering its extreme proximity to the worksite. Hence, a structural monitoring was performed, by investigating the behaviour of the structure before, during and after the dredging. Three main controls were carried out within the monitoring campaign: (a) check of the vibration levels and comparison with thresholds provided by the current Italian prescriptions for human comfort and structural damages; (b) operational modal analysis to assess the possible variations of the structural behaviour during dredging; (c) calibration of a numerical model to simulate the structural behaviour of the sentry building and to derive unknown geometrical and mechanical parameters. A full description of the reference building (characterized by a certain irregularity degree) and all the monitoring phases are reported throughout the manuscript. The results show that, over the monitoring period, the dredging vibration levels never exceeded the thresholds provided by code provisions, and subsequently, the sentry building did not report structural damages, as confirmed by the continuous control of dynamic parameters from experimental and numerical models. In addition, the contents of the paper show the paramount importance of the structural health monitoring, and the experience herein reported can inspire the management of buildings under particular actions like the ones herein investigated.