The existence of structural strength in undisturbed soil results in its distinct characteristics compared to remolded soil. Under the influence of freeze–thaw cycles, this difference may easily cause geotechnical disasters in cold regions. This study aimed to analyze and discuss the expression degree and influencing factors of the structural strength of expansive soil. The unconfined compressive strength (UCS) test, high-pressure consolidation test, and microscopic test were performed on expansive soil retrieved from a seasonally frozen region. Moreover, sensitivity parameters, including stress sensitivity (St.qu, St.σk) and strain sensitivity (St.ɛu, St.Cc), were applied to explore the expression degree and influencing factors of structural strength in a seasonally frozen region. The results reveal that the undisturbed samples have better structural connection and particle arrangement than the remolded samples. However, the primary fractures have a certain degrading effect on the strength of the undisturbed soil as influenced by a seasonally frozen region. With the increase in water content and the decrease in density, the expression degree of the structural strength in terms of compressive strength and the ability to resist deformation enhances under the unconfined condition. By contrast, the expression degree increases in strength and decreases in ability under the confined condition. Furthermore, the effect mechanisms of the basic property, particle composition, structural linkage, lateral confinement, and historical role on the structural expression were analyzed.