Background and Objectives: The goal of this study is to assess health-related quality of life (HRQoL) using the EuroQoL (EQ-5D-5L) and identify factors that might contribute to it. Materials and Methods: This is a real-life, observational study involving 234 hypertensive patients from Sofia and Burgas, conducted between January 2024 and July 2024. Patients were interviewed during their regular outpatient examinations and completed the questionnaire independently. Results: In total, 141 out of 234 respondents reported a visual analog scale (VAS) score of 70, and 152 reported a utility score of 0.7. The average VAS scores for males and females were 77.5 and 77.0, respectively, and the utility scores were 0.848 and 0.768, respectively. With advancing age, patients’ quality of life (QoL) decreased from 0.879 to 0.652 utility. Respondents with higher levels of education had higher utility scores (0.848 for bachelor’s/master’s degrees vs. 0.542 for primary education). With an increase in the number of concomitant diseases and prescribed medications, the QoL decreased (0.848 vs. 0.623 and 0.848 vs. 0.736, respectively). Conclusions: This first study of HRQoL using EQ-5D-5L among Bulgarian hypertensive patients revealed relatively high average VAS and utility scores. These results suggest that the disease is under control and that patients are being successfully treated and monitored. Factors such as comorbidity, residence, education, disability, and disease duration significantly affected and worsened patients’ HRQoL.