An increasing frequency of extreme atmospheric events is challenging our basic knowledge about the resilience mechanisms that mediate the response of small mountainous watersheds (SMW) to landslides, including production of water-derived ecosystem services (WES). We hypothesized that the demand for WES increases the connectivity between lowland and upland regions, and decreases the heterogeneity of SMW. Focusing on four watersheds in the Central Andes of Colombia and combining “site-specific knowledge”, historic land cover maps (1970s and 1980s), and open, analysis-ready remotely sensed data (GLAD Landsat ARD; 1990–2000), we addressed three questions. Over roughly 120 years, the site-specific data revealed an increasing demand for diverse WES, as well as variation among the watersheds in the supply of WES. At watershed-scales, variation in the water balances—a surrogate for water-derived ES flows—exhibited complex relationships with forest cover. Fractional forest cover (pi) and forest aggregation (AIi) varied between the historic and current data sets, but in general showed non-linear relationships with elevation and slope. In the current data set (1990–2000), differences in the number of significant, linear models explaining variation in pi with time, suggest that slope may play a more important role than elevation in land cover change. We found ample evidence for a combined effect of slope and elevation on the two land cover metrics, which would be consistent with strategies directed to mitigate site-specific landslide-associated risks. Overall, our work shows strong feedbacks between lowland and upland areas, raising questions about the sustainable production of WES.