Blood pressure variability (BPV) has been associated with the development, progression, and severity of cardiovascular (CV) organ damage and an increased risk of CV morbidity and mortality. We aimed to explore any association between short-term BPV reduction and hypertension-mediated organ damage (HMOD) regression in hypertensive patients 3-year post-treatment initiation regarding BP control. 24-h ambulatory blood pressure monitoring (24 h ABPM) was performed at baseline in 180 newly diagnosed and never-treated hypertensive patients. We measured 24 h average systolic (24 h SBP) and diastolic BP (24 h DBP) as well as 24 h systolic (sBPV) and diastolic BPV (dBPV). Patients were initially evaluated and 3 years later regarding arterial stiffness (PWV), left ventricular hypertrophy (LVMI), carotid intima-media thickness (cIMT), 24 h microalbumin levels (MAU), and coronary flow reserve (CFR). Successful BP treatment was defined as 24 h SBP/DBP < 130/80 mm Hg based on 2nd ABPM and subsequently, patients were characterized as controlled (n = 119, age = 53 ± 11 years) or non-controlled (n = 61, age = 47 ± 11 years) regarding their BP levels. In the whole population and the controlled group, 24 h SBP/DBP, sBPV/dBPV, LVMI, and IMT were decreased. Additionally, LVMI improvement was related with both sBPV (p < .001) and dBPV reduction (r = .18, p = .02 and r = .20, p = .03, respectively). In non-controlled hypertensives, PWV was increased. In multiple linear regression analysis, sBPV and dBPV reduction predicted LVMI improvement in total population and controlled group independently of initial office SBP, mean BP, and 24 h-SBP levels. In middle-aged hypertensive patients, a 3-year antihypertensive treatment within normal BP limits, confirmed by 24-h ABPM, leads to CV risk reduction associated with sBPV and dBPV improvement.