Nature-based solutions (NBS) are currently being deployed in many European Commission Horizon 2020 projects in reaction to the increasing number of environmental threats, such as climate change, unsustainable urbanization, degradation and loss of natural capital and ecosystem services. In this research, we consider the application of NBS as a catalyst for social inclusivity in urban regeneration strategies, enabled through civic participation in the co-creation of green interventions with respect to social cohesion and wellbeing. This article is focused on a social monitoring framework elaborated within the H2020 CLEVER Cities project, with the city of Milan as a case study. Firstly, we overviewed the major regeneration challenges and expected co-benefits of the project, which are mainly human health and wellbeing, social cohesion and environmental justice, as well as citizen perception about safety and security related to the NBS implementation process. Secondly, we examined the relevance of using NBS in addressing social co-benefits by analyzing data from questionnaires against a set of five major indicators, submitted to citizens and participants of activities during pre-greening interventions: (1) Place, use of space and relationship with nature, (2) Perceived ownership and sense of belonging, (3) Psychosocial issues, social interactions and social cohesion, (4) Citizen perception about safety and security, and lastly, we analyzed (5) knowledge about CLEVER interventions and NBS benefits in relation to socio-demographics of the questionnaires’ respondents. Thirdly, we cross-referenced a wind-rose multi-model of co-benefits analysis for NBS across the regeneration challenges of the project. Because of the COVID-19 emergency, in this research we mainly focused on site observations and online questionnaires, as well as on monitoring pre-greening scenarios in three Urban Living Labs (ULLs) in Milan, namely CLEVER Action Labs. Lastly, this study emphasizes the expected social added values of NBS impact over long-term urban regeneration projects. Insights from the pre-greening surveys results accentuate the importance of the NBS interventions in citizens’ perceptions about their wellbeing, general health and strong sense of neighborhood belonging. A wider interest towards civic participation in co-management and getting informed about NBS interventions in the Milanese context is also noted.