Regeneration of urban wastelands can contribute to revitalize and densify some portions of post-industrial European cities. A growing number of urban wasteland regenerations is now promoted by diverse territorial measures. However, it must be recognized that they mostly focus on “green constructions”, leaving aside holistic aspects of the concept of sustainability. Indeed, due to the inherent complexity of these projects, achieving the objectives of sustainable development is not spontaneous. It depends upon a proactive search for global quality, integrated into the project dynamics, and a continuous assessment of sustainability tailored to these sites. In reaction, this paper presents how a strategic integration of sustainability issues into urban wasteland regeneration projects can answer these targets. Preliminary research led to the creation of a theoretical framework, validated by a test application. Consequently, steps to transform this framework into an operational monitoring tool are presented. The resulting tool aims to concretely facilitate the regeneration of urban wastelands into truly sustainable neighborhoods. Urban strategy, wasteland regeneration, sustainable neighborhood, sustainability assessment, indicator system, monitoring tool.