This study defined the physicochemical attributes, composition, and antioxidant capacity of four Polish cultivars of cornelian cherry (CC) at six stages of development and ripening. A total of 52 metabolites were identified by UPLC-ESI-qTOF-MS/MS and quantified by HPLC-PDA. In general, phenolic acids, hydrolyzable tannins, flavonols, iridoids, antioxidant activity, organic acids, and vitamin C decreased, while anthocyanins, malic acid, sugars, and titratable acidity increased. For the first time, we determined the evolution of the CC chemical properties and the metabolic behavior and quantified the individual compounds, and groups of compounds during ripening, in particular gallotannins, ellagitannins, iridoids, and organic acids. The main novelty of our study is that CC is a valuable resource for utilization at different degrees of maturity. We showed that unripe fruits in particular deserve valorization, as they contained the highest content of total bioactive phytocompounds (5589.1–6779.6 mg/100 g dw)—primarily phenolic acids > iridoids > tannins—and the highest antioxidant capacity. The intermediate stages were the most abundant in vitamin C (341.1–495.6 mg/100 g dw), ellagic acid (5.9–31.6 mg/100 g dw), gallotannins (47.8–331.1 mg/100 g dw), and loganic acid (1393.0–2839.4 mg/100 g dw). The ripe fruits contained less bioactive phytocompounds (1403.7–1974.6 mg/100 g dw)—primarily iridoids > phenolic acids > tannins > anthocyanins—and the lowest antioxidant capacity. On the other hand, ripe fruits showed the highest content of anthocyanins (30.8–143.2 mg/100 g dw), sugars (36.4–78.9 g/100 g dw), malic acid (5.5–12.2 g/100 g dw), and, favorably for the nutritional applications, the highest sugar-to-acids ratio (3.0–6.4). Our work illustrates in detail that quality attributes and the content of health-promoting phytocompounds in CC depend on the ripening stage and on the cultivar. These results advance the scientific knowledge about CC. Our findings can be helpful to select the optimal properties of CC for the development of diverse functional foods and phytopharmaceuticals applied in the prevention of civilization diseases.