This study explores the transformative potential of cyber technologies in the preservation, representation, and restoration of architectural heritage. Bridging technical and humanistic dimensions, it examines how tools like Heritage Building Information Modeling (HBIM), As-Designed BIM, and Virtual Reality (VR) support deeper, multilevel, and multitemporal understandings of cultural sites. Central to the research is an experimental restoration project on the castles of Civitella in Val di Chiana (Arezzo), serving as a methodological testbed for a digitally integrated approach. Developed through a scan-to-BIM process, the project yields a high-fidelity immersive ecosystem—both a rigorous model for future restoration and a VR platform enabling access to previously unreachable spaces. Here, representation is not a secondary or illustrative phase but a central, operative component in historical interpretation and architectural design. This approach embraces cyber representation: a digitally mediated, interactive, and evolving form that extends heritage beyond its physical boundaries. The immersive model fosters renewed dialogue between past and present, encouraging critical reflection on material authenticity, spatial transformation, and conservation strategies within a dynamic, participatory, interactive webVR environment. Representation thus becomes a generative and narrative tool, shaping restoration scenarios while enhancing analytical depth and public engagement. The study ultimately proposes a shift in historical storytelling toward a polyphonic, experiential, cyber-mediated narrative—where technology, memory, and perception converge to create new forms of cultural continuity.