We evaluated the genotype and maturity effects on antioxidant activity and phenolic compounds of whole, skin and pulp fruits from three highbush blueberry cultivars (cv. Brigitta, cv. Bluegold and cv. Legacy) grown in southern Chile. Total antioxidant activity (TAA) in ripe fruits varied among the cultivars in the order Legacy > Brigitta > Bluegold. We found that TAA in unripe green and fully ripe fruits was high and similar between them, whereas the lowest levels were found in intermediate ripe fruits. The same trend was observed for fruit total phenolic content. This could be attributed to the higher concentrations of phenolic acids (mainly chlorogenic acid) and flavonols (mainly rutin) at immature fruit stages; whereas the high TAA in mature fruits could be explained by the elevated amounts of anthocyanin. All antioxidant compounds were mostly located in the skin. High amounts of delphinidin aglycone were found. HPLC-DAD/MS revealed that the main contents of skin anthocyanins are petunidin-3-glucoside and petunidin-3-arabinnoside followed by malvidin-3-galactoside. It is noticeable that highbush blueberry fruits grown in southern Chile have exceptionally higher antioxidant activity and anthocyanins contents compared with those cultivated in the northern hemisphere.