Studying historical rural landscapes beyond their archaeological and cultural significance, as has typically been addressed in previous research, is important in the context of current environmental challenges. Some historical rural landscapes, such as Roman land divisions, have persisted for more than 2000 years and may still contribute to sustainability goals. To assess this topic, the hydraulic and vegetation network of the centuriation northeast of Padua were studied, emphasising their multiple benefits. Their length, distribution, and evolution over time (2008–2022) were vectorised and measured using available digital terrain models and orthophotographs in a geographic information system (GIS). The results revealed a significant decline in the length of water ditches and hedgerows across almost all examined areas, despite their preservation being highlighted in regional and local spatial planning documents. These findings indicate the need for a better understanding of the local dynamics driving such trends and highlight the importance of adopting a more tailored approach to their planning. This study discusses the GIS metrics utilised and, in this way, contributes to landscape monitoring and restoration actions. Finally, a multifunctional approach to the sustainable planning of this area is proposed here—one that integrates the cultural archaeological heritage in question with environmental preservation and contemporary climate adaptation and mitigation strategies.