An extended measurement campaign was carried out in order to investigate the characteristics of High Sound Insulation Ventilating Windows (HSIVW), a proper solution in all the cases where the intervention on noise sources results unfeasible, such as buildings strictly close to motorways or railways, as well as to industrial plants. The first series of tests was implemented on different HSIVW prototypes equipped with aerators (with and without fans); afterwards, a filter was inserted in the aerator, to make the inlet airflow cleaner. Finally, an insulated rolling shutter box was added to four different prototypes: two with an aluminum frame and two with a PVC frame. For all the surveys the sound reduction index (R) and the single number sound reduction index (RW) were calculated, in compliance with the ISO 140/3 method, giving complete informations about the performances of the whole window. The global campaign shows that the windows designed with particular details care present high sound insulation properties, even those equipped with critical components, such as aerators or rolling shutter boxes. The PVC frames show better performances than the aluminum ones, even if all the different types of windows show significantly high values of RW.