This study explores the 4D reconstruction of part of the monumental heritage of St. Mark’s Square in Venice, contextualizing the modeling of its evolution in the broader field of digital historiography. The presented methodology is based on comparing the plausibility of proposed 3D models with current point cloud and historiographical hypotheses that have been compared to the problem of planimetric and volumetric simulation of buildings. Methods include integrating 3D modeling with temporal data to simulate architectural and urban evolution, providing a dynamic and problematic visualization of historical changes and identifying discordant historiographical assumptions. Aligning 3D model reconstructions with the current point cloud provides a better understanding of the plausibility of reconstructions proposed by historiography while identifying potential errors and inconsistencies in some historical documentary sources on which reconstructive approaches are often based. For the reconstructions proposed here, the paper provides an assessment of the level of uncertainty based on some recent notions related to quantifying average uncertainty. Although preliminary, these results provide a basis for testing hypotheses about Venice’s architectural past. Moreover, they open up a new, more generic perspective for the analysis of architectural–urban transformations, based on the notion of planimetric and volumetric constraints, and their comparison with current point cloud records. Using this methodology, we are able to make some solid points with respect to reconstructive hypotheses of the past and indicate which historiographical theories are more plausible than others.