Diabetes mellitus is a group of metabolic disease, which has become globally prevalent, and affects a large population in socio-economically backward countries in Asian continent. Chronic diabetes can lead to ulceration in the plantar region and may result in amputation. Assessment of mechanical properties of plantar tissues can aid in early diagnosis of ulceration. Myotonometry, a technique to measure dynamic stiffness, is preferred due to its noninvasiveness, easy employability, and rapid investigation. In this study, an attempt has been made to analyze the changes in biomechanical properties of plantar soft tissue in diabetes. MyotonPro, a handheld device, is used for this purpose. 43 diabetic subjects with varied duration of diabetes are recruited. Site-specific mechanical properties of the plantar region for both the feet are acquired and statistical analysis is performed. Results show that the MyotonPro is able to differentiate the stages of diabetes. It is seen that there is a spatial variability in the mechanical properties of the plantar. Additionally, it is observed that there is a significant increment in the plantar stiffness value in the group with higher diabetic age (p < 0.05). Further, significant changes in dynamic mechanical properties are also observed in submetatarsal region. Additionally, a right–left asymmetry has been observed in frequency and stiffness values for later stages of diabetes. This study demonstrated the feasibility of MyotonPro in discriminating the stages of diabetic period. Thus, the proposed approach could be useful in early diagnosis of foot ulceration for various clinical conditions.