In this analysis of the telehealth-based Vascular health ASsessment Of The hypertENSive patients Registry, we checked how 24-h central and peripheral hemodynamics compare with hypertension-mediated organ damage (HMOD). In 646 hypertensive patients (mean age 52 ± 16 years, 54% males, 65% treated) we obtained ambulatory brachial and central SBP and pulse pressure (PP), SBP, and PP variability, pulse wave velocity and augmentation index with a validated cuff-based technology. HMOD was defined by an increased left ventricular mass index (cardiac damage, evaluated in 482 patients), an increased intima-media thickness (vascular damage, n = 368), or a decreased estimated glomerular filtration rate or increased urine albumin excretion (renal damage, n = 388). Ambulatory SBP and PPs were significantly associated with cardiac damage: the largest odds ratio was observed for 24-h central SBP [1.032 (1.012, 1.051), P = 0.001] and PP [1.042 (1.015, 1.069), P = 0.002], the weakest for brachial estimates. The association was less strong for vascular damage with a trend to the superiority of 24-h central [1.036 (0.997, 1.076), P = 0.070] over brachial PP [1.031 (1.000, 1.062), P = 0.052]. No statistically significant association was observed for renal damage. SBP and PP variabilities, pulse wave velocity and augmentation index were not associated with any form of HMOD. In the multivariate analysis, age was associated with any type of HMOD, whereas central SBP and PP were predictive of an increased risk of cardiac damage. In hypertensive patients a variable association exists between peripheral and central hemodynamics and various types of HMOD, with the most predictive power being observed for central SBP and PP for cardiac damage.