The Pont del Dimoni (Devil’s Bridge) in Girona, originally built in 1357, is a significant example of Gothic masonry architecture. Dismantled in the 1960s during river diversion works, the bridge was reconstructed in 2019 using approximately 100 original stones—primarily keystones—which now comprise 75% of the arch. Notably, the reconstructed bridge integrates a discreet internal post-tensioning system—an uncommon feature in heritage masonry structures—designed to ensure long-term structural stability while adhering to conservation principles of minimal and reversible intervention. This study presents a comprehensive structural and digital workflow supporting the reconstruction and assessment of the bridge. Photogrammetric surveys across three seasonal campaigns captured the as-built geometry, enabling the generation of BIM-compatible models and updating finite element simulations. These analyses identified seasonal stress variations and validated the performance of the post-tensioning system, confirming full compression in the reconstructed voussoirs. Advanced digital tools, including Grasshopper and Karamba3D, were used to process the point clouds and visualize principal stress. The geometry and structural metadata were then structured and exported to IFC using the MatchFEM plugin, integrating the bridge into an HBIM environment. This model supports future sensor integration, enabling real-time monitoring and digital twinning for long-term structural health assessment. The methodology bridges traditional masonry knowledge with advanced photogrammetry, simulation, and IFC-based data structuring. The Pont del Dimoni thus serves as a replicable case study where historical reconstruction meets modern engineering and digital heritage preservation.