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The subject of the paper is the street, seen as a structuring and emblematic element of urban settlement. The topic is addressed from the lens of regenerative design, whose underlying whole-system, multi-scalar, and dynamic approach can find urban connections to be a fruitful field of experimentation from the perspective of the post-automobile city. The first part of the paper traces the stages of the transport mechanization process and related impacts on urban patterns, emphasizing the voices critical of reducing streets to mere traffic channels that have accompanied it, until the sustainability discourse led to a general rethinking of how mobility should be planned in cities. The second part of the paper reviews alternative urban visions to the still prevailing car-oriented model, which re-actualize the idea of the street as a multifunctional space, providing social and environmental ‘returns’ in addition to its role as a transport infrastructure. The notion of the street as a ‘space of potential’ is then developed through an inductive classification of regenerative actions at different scales, both material and immaterial, as well as permanent and temporary, thus providing a unifying conceptual framework for further research and practical applications in the fields of urban design and sustainable mobility.