This study reconstructs the recent history of Therasia by examining the interplay between traditional settlements and the island’s natural and agricultural landscape. Through an interdisciplinary approach that integrates spatial and architectural analysis, historical records, and NDVI-based vegetation mapping, this research highlights the significant impact of agrarian structures like dry-stone walls and terraces on the environment. The unique dry-stone wall and terrace system is shown to have been crucial for both spatial organization and the survival of Therasia’s inhabitants. This study also addresses the challenges of dating these structures, employing a relative dating methodology to establish a timeline of habitation from the late medieval period to the present. This research reconstructs the island’s recent history, from early seasonal settlements to the eventual decline of rural architecture in the 20th century. The findings indicate that settlement patterns were closely linked to environmental and geomorphological factors, with the evolution of these sites driven by agricultural practices and broader socio-economic changes. This research not only reconstructs Therasia’s past, but also proposes a novel methodological framework combining remote sensing with traditional historical analysis, offering new insights into the relationship between human settlements and the environment in the Aegean region.