Oxidative degradation compromises the sensory, healthy, and commercial value of extra virgin olive oil (EVOO) by depleting antioxidants and producing undesirable off-flavour compounds. Therefore, selecting appropriate primary packaging materials is crucial for preserving the shelf life and overall quality of EVOO. This comparative study evaluated the influence of three packaging materials on the physicochemical and sensory properties of EVOO under conditions simulating typical household storage and use. The same EVOO was stored in polyethylene terephthalate (PET), bag-in-box (BB), and chrome-plated tin (CPT) containers (3 L) and exposed to 25°C under a 12-hour light/dark cycle. To mimic household consumption, 75 mL of EVOO was withdrawn daily and collected over 40 days. Every 10 days, legal quality parameters (free acidity, peroxide value (PV), K₂₃₂, and K₂₇₀), phenolic and volatile compounds, as well as sensory attributes of EVOOs, were monitored. The type of packaging material significantly affected the oxidative stability and overall quality of the EVOO during household consumption. Free acidity, K₂₃₂, and K₂₇₀ slightly increased across all containers, while PET exhibited a significant rise in peroxide value, exceeding regulatory limits. In addition, EVOO stored in the PET container experienced losses of 44% in α-tocopherol and 26% in total hydrophilic phenols. In contrast, there were only 1% and 11% reductions for EVOOs stored in BB and CPT containers, respectively. A significant decline in C₅-C₆ aldehydes and C₆ esters, associated with the “green” attributes of EVOOs, occurred for PET-packaged EVOOs compared to BB and CPT, with a higher accumulation of C₇-C₉ aldehydes and 3-methyl-1-butanol, which are responsible for rancid and winey–vinegary defects, respectively. Among the three packaging materials tested, PET offered lower protection against oxidation than BB or CPT. The EVOOs stored in BB and CPT retained more antioxidants, developed fewer off-flavour compounds, and maintained the oil’s compliance with extra virgin standards.