Urban planning is a challenge, especially when it comes to limiting land take. In former industrial regions such as Wallonia, the presence of a large number of brownfields, here called “redevelopment sites”, opens up new opportunities for sustainable urban planning through their revalorization. The Walloon authorities are currently managing an inventory of more than 2200 sites, which requires a significant amount of time and resources to update. In this context, the Sentinel satellites and the Terrascope platform, the Sentinel Collaborative Ground Segment for Belgium, enabled us to deploy SARSAR, an Earth observation service used for the automated monitoring of redevelopment sites that generates regular and automatic change reports that are directly usable by the Walloon authorities. In this paper, we present the methodological aspects and implementation details of the service, which combines two well-known and robust methods: the Pruned Exact Linear Time method for change point detection and threshold-based classification, which assigns the detected changes to three different classes (vegetation, building and soil). The overall accuracy of the system is in the range of 70–90%, depending on the different methods and classes considered. Some remarks on the advantages and possible drawbacks of this approach are also provided.