Useful information about the oxidative stability of a virgin olive oil in terms of oxidation products and antioxidant compounds can be obtained by analyzing the peroxide index (PI) and total phenolic content (TPC), respectively. These quality parameters are usually determined in a chemical laboratory using expensive equipment, toxic solvents, and well-trained personnel. This paper presents a novel portable sensor system for in the field and rapid determination of PI and TPC that is particularly suited in the case of small production environments that cannot afford an internal laboratory for quality control analysis. The system is small, can be powered by both USB ports and batteries, is easy to operate, and integrates a Bluetooth module for wireless data transmission. It estimates the PI and TPC in olive oil from the measurement of the optical attenuation of an emulsion between a reagent and the sample under test. The system has been tested on a set of 12 olive oil samples (eight for calibration and four for validation), and the results have shown how the considered parameters can be estimated with good accuracy. The maximum deviation from the results obtained with the reference analytical techniques is 4.7 meq O2/kg in the case of PI and 45.3 ppm in the case of TPC for the calibration set, while it is 14.8 meq O2/kg in the case of PI and 55 ppm in the case of TPC for the validation set.