The application of advanced photogrammetry and the integration of cross-sourced maps of historic cityscapes contribute to a thorough understanding of our surrounding, enabling the comparison between present physical layout/use of the built environment and its changes over time. Remote surveys integrated with the analysis of building dossiers, stored in municipal archives, and onsite surveys are carried out in this work for providing insight into a traditional building typology in Portugal, which is so far overlooked in heritage studies. Two examples of humble multi-family dwellings with overhanging timber-framed façades (16th century) are virtually reconstructed using structure-from-Motion (SfM) of selected historic photographs. During a first phase, a photogrammetric reconstruction of the state of the buildings, as conceived originally, was implemented by reconstructing two parts (due to the number of images available for each case study), and then a metric evaluation of the models was conducted comparing past and current state of the buildings. This research shows the importance of integrating distinct tools and databases to foster truly tourists' perception of authenticity in cultural heritage sites and towards a more sensitive heritage management. Potential interactive applications capable of increasing the visibility and impact of these virtual reconstructions, such as GIS data enrichment or digital travel apps, are also briefly discussed.