This experience report presents a model-driven approach to legacy system modernization that inserts an enriched, technology-agnostic intermediate model between the legacy codebase and the modern target platform, and reports on its application and evaluation. The four-stage process of analysis, enrichment, synthesis, and transition systematically extracts, abstracts, and transforms system artifacts. We apply our approach to a large industrial application built on .NET Framework 4.0 and ASP.NET MVC 3 and show that core user interface components and page structures can be migrated semi-automatically to a modern web stack while preserving functional behavior and essential non-functional qualities. By consolidating architectural knowledge into explicit model representations, the resulting codebase exhibits higher maintainability and extensibility, thereby improving developer experience. Although automation is effective for standard patterns, migration of bespoke layout composites remains challenging and requires targeted manual adaptation. Our contributions are: (i) an end-to-end model-driven process, (ii) an enriched intermediate model that captures structure, dependencies, and semantic metadata, (iii) transformation rules that preserve functional behavior and essential non-functional qualities, and (iv) application and evaluation of the approach in an industrial setting. Overall, model-based abstractions reduce risk and effort while supporting scalable, traceable modernization of legacy applications. Our approach generalizes to comparable modernization contexts and promotes reuse of migration patterns.