Today’s complex urban challenges require an integrated approach to regeneration at multiple levels: from international policies to national and local levels. It is also important to stress the urgency of raising awareness and involving citizens in decision-making and co-determination. It is necessary to respond to the commitments made by local authorities through the adoption of voluntary instruments and mitigation policies directly related to social life, using the practices of communication, social innovation, exploitation, dissemination, and networking that the EU considers fundamental to the New Urban Agenda 2030. In this process, residents play a key role in deciding on their places. Through a participatory approach aimed at community development, it is possible to change perceptions of relationships with stakeholders who, together with tenants, can contribute to the regeneration of places at risk. The work presents two case studies in the suburbs of the metropolis of Milan (Italy), which, although very different in terms of institutional realities, have similar characteristics: the first case concerns a public district of Milan (S. Siro), while the second is a private neighbourhood (Crocetta) in the municipality of Cinisello Balsamo. Working with the residents was key to managing the socio-economic-environmental impact of the planned interventions. The Urban Neighbourhood Laboratories were promoted by the municipalities as part of the “Neighbourhood Contracts” programme, which has involved many districts in the Milan metropolitan area since 1998/2000. Originally conceived by the municipalities to inform and communicate with residents about urban projects, over the years they have transformed into places to promote a variety of activities related to participation, community development, co-creation, and business/social innovation actions. The Living Lab EU network (ENoLL) was born out of these bottom-up processes, bringing local experiences to an international audience. The paper aims to demonstrate that only a place-based approach, using innovative methods and skilled practitioners, can deliver effective results over time.