By investigating the intimate dynamics of urban–rural interactions, the present contribution envisions the emergence of fragmented (and, possibly, ‘void’) landscapes within contemporary metropolitan regions, focusing on low-density settlement expansion, green infrastructures, and processes of socioeconomic integration. Urban sprawl has produced heterogeneous and often discontinuous spaces, including abandoned land plots, infrastructural corridors, and other forms of mixed landscapes with negligible value—either economic and ecological. These phenomena reflect the interplay of speculative development, regulatory insufficiencies, and socioeconomic transformations, challenging traditional notions of planning, landscape identity, and environmental stewardship. The contribution also examines patterns of decentralization and socio-spatial segregation, emphasizing the role of peri-urban fringes in ecological balance and economic performances. Particular attention is given to the inherent transformation of urban voids into non-places, which crystallize the tensions between growth-oriented development, cultural heritage conservation, and sustainable land management. The study proposes that vacant and peripheral spaces should be understood as critical lenses for urban analysis, offering insights into the contradictions of modern urbanization and potential avenues for intervention. By integrating historical perspectives with contemporary urban realities, this work definitely underscores the importance of holistic, landscape-sensitive planning approaches that balance ecological integrity, social cohesion, and economic vitality. Ultimately, the findings advocate for a strategic rethinking of metropolitan growth, where the fringe operates not as a residual zone, but as a mediator between city and countryside, capable of fostering resilient, multifunctional, and sustainable urban futures.