Remote sensing techniques, namely Unmanned Aerial Vehicle (UAV) photogrammetry and t-LiDAR (terrestrial Light Detection and Ranging), two well-established techniques, were applied for seven years in a mountainous Mediterranean catchment in Greece (Ilioupoli test site, Athens), following a wildfire event in 2015. The goal was to monitor and quantify soil erosion and sedimentation rates with cm accuracy. As the frequency of wildfires in the Mediterranean has increased, this study aims to present a methodological approach for monitoring and quantifying soil erosion and sedimentation rates in post-fire conditions, through high spatial resolution field measurements acquired using a UAV survey and a t-LiDAR (or TLS—Terrestrial Laser Scanning), in combination with georadar profiles (Ground Penetration Radar—GPR) and GNSS. This test site revealed that 40 m3 of sediment was deposited following the first intense autumn rainfall events, a value that was decreased by 50% over the next six months (20 m3). The UAV–SfM technique revealed only 2 m3 of sediment deposition during the 2018–2019 analysis, highlighting the decrease in soil erosion rates three years after the wildfire event. In the following years (2017–2021), erosion and sedimentation decreased further, confirming the theoretical pattern, whereas sedimentation over the first year after the fire was very high and then sharply lessened as vegetation regenerated. The methodology proposed in this research can serve as a valuable guide for achieving high-precision sediment yield deposition measurements based on a detailed analysis of 3D modeling and a point cloud comparison, specifically leveraging the dense data collection facilitated by UAV–SfM and TLS technology. The resulting point clouds effectively replicate the fine details of the topsoil microtopography within the upland dam basin, as highlighted by the profile analysis. Overall, this research clearly demonstrates that after monitoring the upland area in post-fire conditions, the UAV–SfM method and LiDAR cm-scale data offer a realistic assessment of the retention dam’s life expectancy and management planning. These observations are especially crucial for assessing the impacts in the wildfire-affected areas, the implementation of mitigation strategies, and the construction and maintenance of retention dams.