The present study aimed to evaluate the psychometric properties of the Greek version of the Jefferson Scale of Empathy—Student version (JSE-S) and its association with potential predictors among Greek-speaking undergraduate medical students. This study adopted a cross-sectional, comparative–descriptive research design. The study was conducted during October and November 2023. Cronbach’s α values for the JSE-S and the factors “perspective taking”, “compassionate care”, and “standing in the patient’s shoes” showed internal consistency. The intraclass correlation coefficient for the JSE-S score in the test–retest study indicated a high level of reliability. The participants showed moderate empathy levels. Females scored higher than males in the Greek version of the JSE-S. Moreover, students enrolled in the fourth academic year showed higher empathy mean scores than those enrolled in the first year. Statistically significant empathy differences by specialty preferences or faith in God/supreme power were not found. The present study provided satisfactory evidence that the Greek JSE-S is a psychometrically sound measurement instrument. Empathy differences by gender were found in line with prior literature.