The transition to a sustainable economic and environmental management of olive oil sector needs to be implemented in both national and regional territories through the introduction and development of innovative growing systems and variety. In this study, the olive oil quality parameters of local and allochthonous varieties cultivated in different orchards located in the Abruzzo region (Italy), using traditional and super high-density systems, were analyzed. Frantene, Lecciana, Koroneiki, and a mix of Arbequina and Lecciana provided olive oils rich in flavonoids and secoiridoids compounds with respect to the local varieties Frantoio, Leccino, and a mix of Dritta, Leccino, and Pendolino. Oleic/linoleic ratio was influenced by cultivar and training systems with super high-density olive oils rich in oleic acid. Frantene showed a peculiar fatty acid profile different from cultivars grown in the same location; moreover, interesting similarities were found between Frantene and the mix of Dritta, Leccino, and Pendolino in terms of health-related compounds. The potential development of innovative sustainable training system to improve olive oil quality was highlighted. The study’s results identify olive varieties suitable for super high-density systems spread in the Abruzzo region, representing a valid alternative for the olive growers to improve both the quality of the olive oil, as well as the company’s income.