As the number of people living in cities continues to increase and as their needs continue rapidly to evolve, planners and scholars have been encouraged to define what constitutes high levels of quality of life in urban settlements. The relationship of an area’s inhabitants with natural and green resources increases urban environmental value, which is one of the most relevant aspects in the determination of the quality of life in built-up contexts. Moreover, it is fundamental to find quantitative parameters that can monitor the development of planning processes, working together with natural systems. The authors present a comparative method that can be used to analyze and evaluate the ecological value of urban settlements, using a semi-automatic process that is based on calculating the biotope area factor (BAF) using different open-access databases (a cartographic dataset, aerial imagery, and Sentinel-2 images). Two different Italian case studies that are set in the Milan metropolitan area are presented. In this paper, the authors describe the two settlements using the city-planning parameters of physical structure and morphology; they show the ecological differences and similarities throughout the various remote sensing sources and data. Finally, the authors indicate how the research can be developed, highlighting the weaknesses, the potentiality, the replicability process, and the urban planning implications of the methodology.