This study presents an integrated methodological approach for sustainable urban planning applied to the case study of Milan Rogoredo, a peripheral district of Milan characterized by complex social and environmental challenges. The applied methodology combines conventional analysis tools, such as SWOT+STEEP analysis, with mixed techniques such as Stakeholder analysis (Power Interest and Social Network Analysis) and Multi-Criteria Analysis, with particular emphasis to the Analytic Hierarchy Process (AHP). The main objective is the identification of the most advantageous solution in terms of district regeneration, considering a broad spectrum of interconnected factors, including environmental, social, and economic aspects. SWOT+STEEP analysis has allowed to investigate the current state of the site, identifying strengths, weaknesses, opportunities, and threats, laying the foundation for the subsequent phases of analysis. Stakeholder analysis has highlighted the levels of power and interest of the actors involved, while Multi-Criteria Analysis has allowed the evaluation of three alternative development scenarios. The results of the study demonstrate that the strategic scenario, which emphasizes social inclusion and environmental sustainability, is the most advantageous solution for achieving an urban transformation of Milan Rogoredo. This transformation is aimed at positioning the district as a pole of attraction and social well-being for the entire community. This multilevel methodological approach provides an effective model for urban planning in complex peripheral contexts, promoting decisions oriented towards sustainability and circular regeneration.