Dynamic simulation is a key tool to achieve better building energy performance both optimizing energy usage efficiency and ensuring occupant comfort. Traditional static models often fail to capture the complexity of energy dynamics in real-world scenarios, especially regarding the impact of occupant behavior. This phenomenon occurs more often when the energy usage patterns fluctuate significantly. In this work, ALMABuild, a dynamic simulation tool developed in the MATLAB-Simulink environment, is used to analyze the energy performance of a real student residence in Bologna (Italy). The thermal-hygrometric conditions, including temperature and humidity, and appliances energy consumption are monitored by means of sensors in several dwellings of the student residence. Additionally, two surveys are conducted to assess the occupants’ comfort perceptions and awareness about energy efficiency and saving. The analysis considers both the installed HVAC system and occupant habits. Furthermore, a stochastic algorithm is used to simulate the window opening and closing actions made by occupants, taking into account both external and internal conditions and personal sensitivity. The results indicate that occupant behavior plays a pivotal role on energy performance. The analysis of three distinct occupant profile, categorized by their awareness of energy-related actions, shows that the most energy-aware profile can achieve up to a 60% reduction in energy consumption, while the least favorable profile may lead to a 30% increase. By integrating real-time data, user feedback, and advanced simulation techniques, this research aims to narrow the gap between theoretical building models and practical results, ultimately guiding occupants toward more energy-efficient practices.