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This article contributes to the assessment of the hygrothermal conditions of residential buildings in the Azores archipelago and defines strategies that may contribute to the improvement in indoor air quality. These objectives were fulfilled by in situ monitoring of the hygrothermal conditions of a typical building on Terceira Island. Complementary tests to determine the thermal conductivity of exterior walls and ventilation rates were also conducted. The results were used to validate a simulation model, and different ventilation strategies were simulated using the combined heat, air, and moisture transfer model in EnergyPlus. The model took into account the typical construction methods and materials of the archipelago, as well as the reference weather data sets available for the region. The monitoring campaign showed that the percentage of time in which thermal comfort conditions were achieved was very low, varying from 5% to 32%, being the main cause for discomfort in the humidity level in the indoor environment. The simulation results pointed out the sensitivity of the problem, showing that ventilation may not always be, by itself, beneficial to thermal comfort. In particular, ventilation strategies should be established taking into account additional criteria other than the air change rate, namely the periods of the day and year in which ventilation should be performed, as well as the duration of these periods.