To reduce the vibration and shock of powertrain in the process of engine key on/off and vehicle in situ shift, a novel semi-active hydraulic damping strut is developed. The purpose of this paper is to study and discuss the dynamic stiffness model of the semi-active hydraulic damping strut. In this study, the dynamic characteristics of semi-active hydraulic damping strut were analyzed based on MTS 831 test rig first. Then, the dynamic stiffness model of semi-active hydraulic damping strut was established based on 2 degrees of freedom vibration system. In this research, a linear, fractional derivative and friction model was used to represent the nonlinear rubber bushing characteristic; the Maxwell model was used to describe the semi-active hydraulic damping strut body model; and the parameters of rubber bushing and semi-active hydraulic damping strut body were identified. The dynamic stiffness values were calculated with solenoid valve energized and not energized at amplitudes of 1 mm and 4 mm, which were consistent with experimental results in low-frequency range. Furthermore, the simplified dynamic stiffness model of the semi-active hydraulic damping strut was discussed, which showed that bushing can be ignored in low-frequency range. Then, the influence of equivalent spring stiffness, damping constant, and rubber bushing stiffness on the stiffness and damping capacity of the semi-active hydraulic damping strut were analyzed. Finally, the prototype of the semi-active hydraulic damping strut was developed and designed based on the vehicle in situ shift and engine key on/off situations, and experiments of the vehicle with and without semi-active hydraulic damping strut were carried out to verify its function.