Since the year 2002, the Uruguayan oil-producing sector has been growing at a steady peace, utilizing over 10,000 seeded hectares across the country. The aim of this study was to characterise both the chemical and sensory properties of the extra virgin olive oil variety known as Arbequina through two consecutive harvests. The work was carried out using olives with three different ripening indices; the oil was extracted using an Abencor system. The moisture of the olive, yield extraction, and yield on both a dry and wet basis were determined. The obtained oils were characterized by determining the free acidity, main antioxidant compounds (polyphenols and tocopherols), composition of fatty acids, and sensory profiles. Olive moisture was over 57%, which led to production of pomaces characterized as “difficult pastes”, explaining the low yield obtained. The harvest year and ripening index affected different parameters such as Abencor yield and, on a dry basis, the free acidity, polyphenolic content, oleic acid, and linoleic acid contents and fruity, bitter, and pungent intensities. To determine the best time of harvest, it is important to consider the balance between yield (which is significantly greater in olives with a ripening index above 3) and oil quality, as a higher ripening index decreases positive sensory attributes such as pungency and bitterness intensities.