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The building sector greatly contributes to energy consumption and Greenhouse Gas emissions, relating to the whole building life cycle. Boasting a huge building heritage of historical and architectural value, Europe faces challenging retrofit perspectives, as the potential for high energy efficiency has to be exploited while preserving the buildings' original characteristics. The present work aims to feature the influence of a passive strategy on a heritage building in a mild climate. As historical its façade cannot be modified, its large glazing areas involve multiple issues, such as an increase in the heating ( Q H) and cooling ( Q C ) energy demands and the risk of thermal discomfort. Thus, window replacement was proposed for retrofitting. A dynamic simulation model in TRNSYS was validated with experimental data collected by the continuous monitoring of walls of different thicknesses and orientations. Solutions from replacement with Double Glazing Units (DGUs) with improved thermal insulation, to internal shading activation were applied. All configurations were compared in terms of Q H , Q C , thermal performance of the building and user comfort (Fanger). Low-e DGU enabled the saving of up to 14% of the annual energy demand, and shading also offered good results in summer, reducing Q C by 19%. In summer, DGU involved a maximum PPD reduction of 10 units. [ABSTRACT FROM AUTHOR]