Wind pressure coefficients (Cp) are important values for building engineering applications, such as calculation of wind loads or wind-induced air infiltration and especially for tall buildings that are more susceptible to wind forces. Wind pressure coefficients are influenced by a plethora of parameters, such as building geometry, position on the façade, exposure or sheltering degree, and wind direction. On-site measurements have been performed on a twin medium-rise building complex. Differential pressure measurements have been employed in order to determine the wind pressure coefficients at various positions along the windward façades of the twin buildings. The measurements show that one building provides substantial wind shelter to its twin and the microclimatic effect is captured by the measured wind pressure coefficients. They also showed that the wind pressure coefficients vary significantly spatially along the windward façades of the medium-rise buildings. Furthermore, the pressure measurements showed that the wind pressure coefficients fluctuate significantly during the measuring period. The use of the fluctuating Cp values by means of probability distribution function (pdf) for the calculation of air infiltration has been evaluated. The results indicate that the air flows deriving using fluctuating Cp values are more accurate than the ones calculated by the conventional method of using mean Cp values.