Increasing age appears to influence several morphologic changes in major tendons. However, the effects of aging on the cross-sectional area (CSA) of different ankle tendons are much less understood. Furthermore, potential differences in specific tendon regions along the length of the tendons have not been investigated in detail. Sixty healthy adult participants categorized by age as young (n = 20; mean ± SD age = 22.5 ± 4.5 years), middle-age (n = 20; age = 40.6 ± 8. 0 years), or old (n = 20; age = 69.9 ± 9.1 years), from both sexes, were included. The tendon CSA of tibialis anterior (TA), tibialis posterior (TP), fibularis (FT), and Achilles (AT) was measured from T1-weighted 1.5 T MR images in incremental intervals of 10% along its length (from proximal insertion) and compared between different age groups and sexes. The mean CSA of the AT was greater in the middle-age group than both young and old participants (p < 0.01) and large effect sizes were observed for these differences (Cohen's d > 1). Furthermore, there was a significant difference in CSA in all three groups along the length of the different tendons. Region-specific differences between groups were observed in the distal portion (90% and 100% of the length), in which the FT presented greater CSA comparing middle-age to young and old (p < 0.05). In conclusion, (1) great magnitude of morpho-structural differences was discovered in the AT; (2) there are region-specific differences in the CSA of ankle tendons within the three groups and between them; and (3) there were no differences in tendon CSA between sexes.