The concept of sustainability is widely seen as fundamental to set up urban and territorial transformations. Sustainable development is a multidimensional and multi-perspective process that deals with the environmental, economic, and social dimensions, with the aim to find a balance among these. Despite this growing attention to sustainability the social perspective has been the less explored of these dimensions and only recently it is receiving consideration due the Sustainable Development Goals (SDGs) that aim at creating sustainable and inclusive cities and communities. In the SDGs, specific attention is focused on the improvement of the quality of life of inhabitants through specific actions dedicated to the valorization of cultural resources, to the protection of the environment, and also to promote the involvement of the local communities in setting policies and programs. The final objective is defining projects based on the social needs shared by the communities. This paper aims at exploring the social sustainability related to urban regeneration processes with particular attention to social cohesion and community engagement. Six different urban regeneration strategies, developed for the regeneration of an urban area located in Northern Italy and based on social housing interventions, have been evaluated in accordance with their social impacts on the stakeholders involved. The paper proposes a multi-methodological approach based on the combination of the stakeholder analysis with the NAIADE (Novel Approach to Imprecise Assessment and Decision Environments) methodology, a particular type of Social Multi-Criteria Evaluation. The stakeholder analysis has been applied to identify the actors to involve in the evaluation, whereas the NAIADE methodology has been implemented for the selection of the most preferable strategy. This method allowed the assessment of the different strategies through the comparison and the mediation between the technical and the social rankings, thus considering the stakeholder preferences in the final evaluation. The final result is coherent with the initial purpose and it demonstrates that the inclusion of the stakeholder is fundamental for the achievement of a consensus solution.