In Mediterranean semi-arid regions, rainfed olive groves are increasingly being abandoned due to drought, low profitability, and rural depopulation. The long-term impact of abandonment on soil conditions is debated, as it may promote vegetation recovery or lead to degradation. In contrast, some farmers are adopting low-disturbance management practices that allow spontaneous vegetation to establish. These contrasting scenarios offer valuable opportunities for comparison. This study aims to develop a framework to assess the impact of different management regimes on soil health and to investigate (1) the impact of spontaneous vegetation cover (SVC) and tillage regimes on soil organic carbon (SOC), and (2) the long-term ecological dynamics of abandoned groves, through a combination of field surveys, remote sensing, and object detection. SOC was assessed using both ground-based and remote sensing-derived indicators. Vegetation cover was quantified via a grid point intercept method. Field data were integrated with a land-use monitoring framework that includes abandonment assessment through historical orthophotos and a deep learning model (YOLOv12) to detect active and abandoned olive groves. Results show that abandoned zones are richer in SOC than active ones. In particular, the active groves with SVC exhibit a mean SOC of 1%, which is higher than that of tilled groves, where SOC is 0.45%, with no apparent moisture loss. Abandoned groves can be reliably identified from aerial imagery, achieving a recall of 0.833 for abandoned patches. Our results demonstrate the potential of YOLOv12 as an innovative and accessible tool for detecting zones undergoing ecological regeneration or degradation. The study underscores the ecological and agronomic potential of spontaneous vegetation in olive agroecosystems.