Urban pavements absorb large amounts of solar radiation, raising surface temperatures and intensifying the urban heat island effect. These thermal conditions reduce urban comfort, accelerate pavement deterioration, and increase cooling energy demand in surrounding buildings. To address these challenges, previous research has explored different technologies to harness stored heat, including geothermal paving systems, pavement–solar-thermal solutions, and hybrid photovoltaic–thermal pavements. However, several challenges remain regarding the long-term interaction between heat extraction and pavement durability, the influence of climatic variability, and the optimisation of collector geometry, material properties, and hydraulic operation for real urban environments. The ENHANCE Europe project investigates an innovative solution based on asphalt solar collectors embedded within flexible pavement structures. The system aims to recover the excess heat stored in the pavement and convert it into a usable thermal resource for nearby buildings, thereby reducing fossil-fuel consumption, lowering operational energy costs, and enhancing the resilience of urban energy systems. As part of this project, the present work introduces a finite-element numerical framework for simulating coupled heat transfer and fluid flow within multilayer pavement systems and their embedded collector networks. The computational approach solves the Navier–Stokes and heat equations, implementing an Incremental Pressure Correction Scheme to evaluate thermal behaviour under varying environmental and operational conditions. Concretely, the simulations quantify temperature profiles at critical pavement depths, evaluate heat extraction efficiency, and monitor key parameters essential for understanding the system’s performance. The numerical results support informed decision-making for design and construction, enabling the optimisation of geometry, materials, and operating conditions. The simulation will be further refined using real data from four living labs, contributing to the development of digital tools and data-driven methodologies that facilitate the energy transition across European urban areas.