In this paper, we used Landsat imagery for water body identification to create a novel 36-year surface area extent time series for lakes Azuei (Haiti) and Enriquillo (Dominican Republic) aimed at illuminating the dramatic temporal changes of these two lakes not just at yearly but at monthly or even sub-monthly scales. We used the Normalized Difference Water Index (NDWI) to extract water features and we also used spatial differentiation and thresholding techniques to remove clouds and associated shadows from the scene that were then passed through gap filling algorithms to complete and extract the lake extent polygons. We also explored the challenges that arrive from trying to combine RS-based Digital Elevation Model data with locally collected bathymetric data to yield a seamless representation of the topographic features of the rift valley that contains the two lakes. This “bathtub” model was then meshed with the lake extent polygons to compute lake volumes, maximum depths, and geospatially referenced lake levels rating curves. We used this data to examine the lakes and their geospatial characteristics in the context of the lakes’ growth/shrinking patterns. While we did not carry out a full hydrologic analysis we attempted to illuminate how specific lake levels cause what type of flooding and especially answered the questions if (a) Lake Azuei would ever spill into Lake Enriquillo, and (b) what the maximum lake levels need to be before spilling into neighboring watersheds.