In inland areas of Portugal and some regions of the Mediterranean basin, olive production is based on traditional olive groves, with low intensification, local cultivars, aged plants, and centenarian trees. These plants play a key role in the ecosystem, contributing to carbon sequestration and possessing a high genetic diversity, particularly important for selecting cultivars more resistant to climatic changes. Appreciation of the value of this genetic diversity implies genetic, morphological, and physicochemical characterization of centenarian trees, which is expensive and time-consuming. Sensory evaluation is also of utmost importance. Thus, in this study, centenarian olive trees were selected in the Côa Valley region, a UNESCO World Heritage site. The descriptive sensory profile of their extracted olive oils was established and used to cluster the oils, using hierarchical clustering analysis, and consequently the olive trees, into five groups with similar intensities of perceived olfactory–gustatory attributes. Each cluster revealed olive oils with unique sensory patterns, presumably due to similarities of the olive trees, confirming the potential of the proposed screening approach. The identification of sensorially homogeneous oil-tree groups would reduce the number of specimens needed for subsequent morphological, genetic, and chemical characterization, allowing a cost-effective and robust future evaluation procedure.