Contemporary urban contexts are increasingly characterized by spatial fragmentation, environmental stress, and social vulnerability, requiring planning approaches capable of addressing complexity beyond traditional sector-based frameworks. From this perspective, landscape-oriented strategies provide an effective interpretative and operational lens for understanding cities as integrated socio-ecological systems, where environmental processes, spatial structures, and human practices dynamically interact. This contribution explores the role of landscape as a structuring framework for urban regeneration strategies in complex and fragile urban environments. Landscape is interpreted not merely as a physical or perceptual dimension, but as a multi-layered system integrating ecological networks, public spaces, cultural identity, and everyday urban practices. Such an approach enables the identification of spatial relationships, criticalities, and opportunities that can inform adaptive and inclusive regeneration pathways. The study adopts a qualitative and analytical methodology based on spatial interpretation, urban policy analysis, and the examination of contexts characterized by marginalization, infrastructural discontinuities, and environmental vulnerability. Particular attention is given to the capacity of landscape-oriented approaches to support integrated decision-making processes, enhance urban resilience, and promote socially inclusive transformations over time. The findings highlight how landscape-based strategies can contribute to more coherent and context-sensitive urban regeneration processes, fostering stronger connections between environmental quality, social inclusion, and spatial governance. The paper contributes to ongoing debates in urban science by reinforcing the role of landscape as a key driver of sustainable urban transformation.