The research on the rural-urban gradient in Serbia has been reinvigorated following the debate on rural bias. Rural-urban classification is essential in observing spatial, demographic, socio-economic, and environmental processes. There is no consensus regarding the definition of rural and rurality and it should not be observed separately from urban issues. In Serbia, it is still a matter of dispute. Rural is most often observed through the urban–rural dichotomy and “left behind” for decades. This paper strives for a new theoretical understanding of the rurality in Serbia by introducing rural heterogeneity and ‘continuing’ rurality, considering the transformative phase they are affected by. It induces a process of rethinking what rurality in Serbia is and offers an innovative methodological approach for rural delineation and settlement classification based on three main pillars: settlement patterns, functional patterns, and local relevance. The analysis is conducted on the lowest administrative level in Central Serbia. Five types of settlements are identified: two urban, and three characterized by rural features. The combination of abstractions and the methodological opportunities introduced by rethinking rurality offers geographers and practitioners a powerful methodological tool for the understanding of rural transformations and transitional spatial forms, which underpins planning and policy-making in Serbia.