Abstract: Cultivated land represents a critical natural resource for ensuring food security, maintaining ecosystem services, and promoting socio-economic development. Given the mounting pressures of global population growth and climate change, the precise monitoring and scientific assessment of the spatiotemporal evolution of cultivated land hold great significance for regional sustainable development. This study investigated cultivated land in the agropole of the Littoral Region, Cameroon. Based on multi-stage Landsat remote sensing images during 1986—2024, combined with the GlobeLand30 land cover data product and a global oil palm dataset, this study determined the distribution of cultivated land in the study area across different periods using the random forest algorithm. Accordingly, it further analyzed the area changes and spatial distribution patterns of the cultivated land, as well as potential driving factors. The results indicate that from 1986 to 2024, the area of cultivated land in the study area increased significantly from 129.59 km² to 537.62 km², with a cumulative net increase of 408.03 km² and an average annual net increase of approximately 10.74 km². The cultivated land exhibited distinct phases of expansion: rapid expansion from the 1990s to the 2000s, a decelerated growth from the 2000s to the 2010s, and rapid expansion again from the 2010s to the 2020s. Spatially, the expansion of cultivated land in the study area primarily occurred along the northwestern part, progressively advancing toward the central hinterland. In contrast, areas with reduced cultivated land were sparsely distributed across the highly elevated areas within the northwestern part. The expansion of cultivated land was primarily driven by the large-scale planting of cash crops (i.e., cocoa tree, oil palm, and rubber tree), which was subjected to the combined effects of multiple factors including market demand, policy orientation, population growth, and locational conditions. The results of this study provide long-time-series empirical evidence for understanding changes in cultivated land in Cameroon, thereby serving as a valuable reference for formulating policies on regional land resource management and sustainable agricultural development.