Volatile compounds, quality traits (total phenols and antioxidant capacity) and High-performance liquid chromatography (HPLC)-isolated polyphenols of strawberries, variety Sabrosa, commercially referred to as “Candonga”, harvested at three different times (H1, H2 and H3) and at two different ripening stages, namely half-red (Half-red-H1, Half-red-H2 and Half-red-H3) and red (Red-H1, Red-H2 and Red-H3) were evaluated. Dominant anthocyanins, namely cyanidin-3-O-glucoside, pelargonidin-3-O-glucoside and pelargonidin-3-O-rutinoside, as well as p-coumaryl hexoside increased during harvesting, differently from flavonoids, such as quercetin-3-O-glucoside, kaempferol-3-O-glucoronide and quercetin 3-O-glucoronide, that declined. Samples clustered in different quadrants of the principal component analysis (PCA) performed on volatiles, quality traits and phenolic compounds, highlighting that only the red samples were directly correlated to volatile components, as volatiles clearly increased both in number and amount during ripening. In particular, volatiles with a positive impact on the consumers’ acceptance, including butyl butyrate, ethyl hexanoate, hexyl acetate, nonanal, terpenes and lactones, were positively associated with the Red-H1 and Red-H2 strawberries, while volatiles with negative coefficients related to consumer liking, including isopropyl butyrate, isoamyl butyrate and mesifurane directly correlated with the Red-H3 samples. Accordingly, strawberries harvested at Red-H1 and Red-H2 ripening stages could be preferred by the consumers compared to the Red-H3 fruit. Altogether, these results could help to individuate quality traits as putative markers of the ripening stage, and optimize the process of post-harvesting ripening to preserve or improve the desirable aromatic characteristics of strawberries.