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This contribution aims at improving the understanding of the conditions and dynamics that facilitate processes of culture-based urban regeneration via social innovation. It presents and discusses the outcomes of an in-depth investigation of five projects taking place in large cities in Italy dealing with the reuse and regeneration of urban spaces through creative and innovative practices. Research findings demonstrate the centrality of the network dimension in sustaining and shaping processes of urban regeneration through social innovation and cultural production. Networks are led by social entrepreneurs having a strong territorial focus that “cultivate” new values for the local community by reusing and mobilizing publicly owned vacant or abandoned material assets.