This review aims at updating and critically assessing the role of telemedicine, and in particular, of home blood pressure telemonitoring (HBPT), in the management of the hypertensive patient. Result from several randomized trials suggest that HBPT represents a promising tool for improving blood pressure (BP) control of hypertensive patients, in particular, those at high risk. Most studies documented a significant BP reduction with regular HBPT compared to usual care. HBPT interventions showed a very high degree of acceptance by patients, helped improving the patients' quality of life, and were associated with lower medical costs than standard care, even though such costs were offset by those of the technology, thus reducing the overall cost-effectiveness of HBPT. The high heterogeneity of the technologies, study designs, and type of patients in the various studies suggest that further well-designed, large cohort, prospective studies are needed to identify key elements of HBPT approach to be able to give impact on specific outcomes. Likely, patients who need a constant monitoring of multiple vital signs and a tight BP control, such as high risk patients with chronic diseases (ischemic heart disease or heart failure, diabetes, etc.), as well as non-adherent patients, may particularly benefit from HBPT. In general, HBPT can be an advantageous choice when a network among healthcare professionals (doctors, nurses, and pharmacists) is needed to improve the screening and management of hypertension and related comorbidities and to achieve an effective prevention of cardiovascular diseases in the community.