Highway widening is an important way to improve the existing expressway capacity and promote the development of transportation systems. The differential settlement between the old and new subgrade is the key factor to evaluate whether it is necessary to carry out ground improvement for the new foundation, which will cause longitudinal pavement cracking and even subgrade instability. Therefore, the most critical task in the highway expansion project is controlling differential settlement, particularly post-construction differential settlement. In this study, a fluid-structure coupling settlement analysis model was developed based on FLAC3D, and a modified Cam-clay (MCC) model was used to describe the difference between new and old foundation parameters. The working conditions of different subgrade heights and groundwater levels were simulated to analyze their influence on the differential settlement during and after construction. With the increment value of the transverse slope (∆i) and maximum slope (k) of new and old subgrade settlement curves as evaluation indexes, the differential settlement size of widened subgrade under different working conditions is evaluated, which provides a basis for the design of widened foundation engineering and provides suggestions on whether reinforcement measures should be taken. The results show that the post-construction differential settlement increases with the increase in groundwater level and subgrade height. Under the requirement of ∆i ≤ 0.5%, it is not necessary to take reinforcement measures under the condition of local water levels under a 2 m subgrade height and −9 m and −11 m groundwater levels under a 4 m subgrade height. However, when the water level rises further, or the height of the subgrade increases further, it is necessary to take foundation reinforcement measures. Meanwhile, for the requirement of k ≤ 0.5%, foundation reinforcement measures should be taken for all working conditions regardless of the water level or subgrade height. The research results can provide theoretical value and reference for foundation treatment in roadbed-widening engineering.