The evaluation of the influence of olive ripening degree on the stability of extra virgin olive oils by the determination of the oxidative stability index, the DPPH(*) radical test, and the quali-quantitative analysis of phenolic compounds, as well as the study of the variation of their sensory profiles, plays a key role in the assessment of the overall olive oil quality. Olives of the cv. Nostrana di Brisighella grown in the north-central Italian region of Emilia-Romagna were picked at four different stages of ripeness and immediately processed in an experimental mill. The polar extracts of oil samples were submitted to spectrophotometric analysis of total phenols and o-diphenols and to liquid chromatographic determination of their quali-quantitative profile (HPLC-DAD/MSD). To attain a complete description of oil samples, fatty acid composition, ultraviolet indices (K(232), K(270), and deltaK), free acidity degree, and peroxide value were also determined according to the European Union methods stated in Regulation 2568/91 (1, Off. J. Eur. Communities 1991, L248, 1-82). Sensory quantitative descriptive analysis (QDA) and triangular tests were performed to establish the influence of olive ripening degree on the resulting oil's organoleptic properties. The evolution of the analytical parameters studied shows that the ripeness stage of Nostrana di Brisighella olives that yields the best oil corresponds to a Jaén index value between 2.5 and 3.5. Oils produced from olives harvested within this time frame present a superior sensory profile accompanied by the highest possible chemical and nutritional properties.