Land use changes, and especially urbanization, significantly impact water and energy systems and the associated GHG emissions. However, studying these dynamics and their effects on coupled water–energy–emissions systems remains underexplored in certain countries. Greece has been slow to integrate these systems into data-driven models assessing their feedback. To fill this gap, this research investigates these dynamics in Greece from 2022 to 2050, combining different modelling approaches for the first time. A Remote Sensing analysis utilizing publicly available data and open-source tools (QGIS) was applied to map and monitor land use changes, including urbanization. Greece is a particularly interesting case study, as simultaneous population decline and increasing urbanization are reshaping key sectors of the developing urban centers, i.e., the residential and services sectors. To capture the complex feedback between urban centers with changing population and their water–energy–emissions responses, we coupled the LEAP (Low Energy Analysis Platform) model with the WaterReqGCH model. Thus, the energy consumption and the associated GHG emissions of the residential and services sectors, along with their water consumption, were simulated. The results reveal critical trends: population decline drives a reduction in overall water and energy consumption, and yet, despite these reducing trends, urban areas claim increasing shares of these resources over time. Similarly, decreasing GHG emissions exhibit shifts in pollutant distribution, with certain emissions holding larger shares in urban contexts. This integrated land–water–energy–emissions analysis underscores the value of holistic assessments in managing these systems sustainably and highlights the need to develop plans considering them as a whole. The provision of detailed information on such evolution patterns and feedback is critical to shaping integrated policies aiming at multiple benefits. By linking urbanization patterns with resource dynamics and environmental impacts, we discuss how our findings can be translated into actionable insights for sustainable urban planning and resource management strategies.