Extra virgin olive oil (EVOO) is recognized for its numerous health benefits attributed to its rich phenolic components. NMR has emerged as a prevalent technique for precisely identifying these compounds. Among Mediterranean countries, Greece stands as the third-largest producer of olives, with the Epirus region notably advancing in olive cultivation, contributing significantly to the dynamic growth of the region. In this study, an NMR method was employed based on the acquisition of an 1H NMR spectrum along with the multiple resonant suppression in order to increase the sensitivity. Using the above method, 198 samples of extra virgin olive oil, primarily sourced from the Epirus region were analyzed and both the qualitative and quantitative aspects of phenolic compounds were acquired. In addition, we examined the effect of various factors, such as, variety, harvest month and region origin on the phenolic compounds’ concentration. The results revealed an average total phenolic content of 246 mg/kg, closely approaching the EU health claim limit of 250 mg/kg. Approximately 15% of the samples were confidently characterized as high-phenolic olive oil. The highest concentrations were observed in Thesprotia samples, with several Lianolia variety exceeding the total phenolic content of 400 mg/kg. Statistical tests demonstrated a significant influence of the olive variety and the month of fruit harvest on phenolic component concentration, followed by the region of origin. A very strong correlation was noted between the total phenolics content and the levels of oleocanthal and oleacein, with a correlation coefficient (r) of 0.924. Upon optimization of all factors affecting olive oil quality, the majority of EVOO from the Epirus region have the potential to be characterized as high in phenolic content.