Difficult-to-control (DTC) hypertension represents a burden in real life that can be partially solved through identification of the characteristics of clinical patterns and tailoring antihypertensive strategies, including ICT-enabled integrated care (ICT-IC). In the quest for clinical predictors of DTC hypertension, we screened 482 hypertensive patients who were consecutively referred to the departmental hypertension clinic. Following a data quality check, patients were divided into controlled (C, 49.37%) and uncontrolled (UC, 50.63%) groups based on their systolic blood pressure (BP) at follow-up. We then performed statistical analysis on the demographic, clinical, laboratory, and ultrasound data and observed that older age, female sex, higher BP levels, and a family history of hypertension were predictors of DTC hypertension. We then developed a pilot service of ICT-IC, including weekly home visits by nurses and patient education on self-monitoring of BP, heart rate, body weight, and oxygen saturation using 3G-connected devices. Self-monitored data were transmitted to the hospital servers on the electronic chart of the patient for remote assessment by the hospital hypertension specialists. A total of 20 UC patients (M/F = 10/10; age: 72.04 ± 2.17 years) were enrolled to verify the efficacy of BP control without changes in medical treatment. After 1 month of the ICT-IC program, BP was reduced both at the office assessment (systolic BP (SBP): 162.40 ± 2.23 mm Hg, beginning of the program vs. 138.20 ± 4.26 mm Hg at 1 month, p < 0.01) and at home (SBP: 149.83 ± 3.44, beginning of the program vs. 134.16 ± 1.67 mm Hg at 1 month, p < 0.01). We concluded that DTC hypertension can be predicted based on the clinical characteristics at the first visit. For these patients, ICT-IC is a feasible therapeutic strategy to achieve BP control.