This study aims to analyze the dynamics of change in settlement models from the Roman, late antique, and Byzantine periods, focusing on how these transformations influenced the formation of Islamic societies in the rural landscapes of western Sicily. The study is centered around the territory of Corleone in the Sicani Mountains (central-western Sicily). This region, strategically located between the significant cities of Palermo on the Tyrrhenian Sea and Agrigento on the Strait of Sicily, has been pivotal in the communication network spanning from the Roman era to the Middle Ages and beyond. The area has been subject to extensive surveys and excavations, revealing diverse dynamics of continuity, resilience, and innovation in settlement patterns from the Roman to the Islamic periods. Beyond presenting the results of archaeological fieldwork, this study employs GIS-based spatial and statistical analyses and utilizes a range of topographic (elevation, slope, aspect, topographic position index (TPI), and distance to water sources) and ecological factors (vegetation series). These analyses aim to assess the evolving relationships and site positioning within the territory over time. Combining archaeological data with topographic and ecological landscape analysis, this integrated approach elucidates the complex transition dynamics from the Roman settlement system to the Islamic age’s landscape formation in western Sicily’s rural areas. The study thereby contributes to a deeper understanding of the intricate interplay between historical developments and environmental factors in shaping rural settlement patterns.