The aim of the article is to describe the results of an experimental campaign based on the assessment of a heat recovery unit coupled with a dynamic window. Two fully monitored and calibrated outdoor test cells are used, in order to evaluate the energy performance and the related thermal comfort. The former presents a traditional window with double-glazing, aluminum frame and indoor blind and a centrifugal extractor for the air circulation. The latter is equipped with a dynamic window with ventilated and blinded double-glazing provided with a heat exchanger. The connection of the dynamic window and heat recovery unit provides different actions: heat recovery; heat transfer reduction; pre-heating before the exchanger. Different operating configurations allowed the trends of the dynamic system to be assessed in different seasons in terms of energy saving, thermal comfort behavior and energy efficiency. The results showed an overall lower consumption of the innovative system, both in winter and summer, with 20% and 15% energy saving, respectively. In general, the dynamic system provided the best comfort conditions, even if it involves a worse behavior than expected, in the summer season.