This study aims for a wider understanding of the redevelopment processes that emerged several decades ago in downtown San Diego and now gradually spread over the downtown edges into the inner ring. Perspectively situated in the fields of urban landscape and urban border studies, the research project outlines how the eastward ‘redevelopment wave’ in San Diego contests socialized neighborhood (boundary) perceptions by transforming the former first-tier suburbs from disinvested communities into ‘urban villages’ and trendy places to be. The study shows how the redevelopment perforates, dissolves, and shifts socialized, linear neighborhood boundaries into areas that are simultaneously part of the one and the other neighborhood. In the present work, the resulting, rather undefined or stretched border areas have been referred to as hybrid urban borderlands. This notion is a novel conceptual approach that can be deemed a promising lens for future studies on neighborhood change, urban redevelopment, and socio-spatial re-interpretation beyond the context of San Diego.