Due to improvements in the use of recyclable materials in construction, timber–steel composite (TSC) beams demonstrate high potential for future construction. In this study, a proposed simulation modeling, which was adopted from the simulation modeling of a timber I-shape composite, was applied to estimate the initial stiffness of TSC beams. The strength of each beam could be determined once the initial stiffness was estimated. In addition, a series of experiments were performed to examine the accuracy of the proposed simulation modeling, including the effects of different shapes of steel members, fasteners, and applying and not applying a dowel connection. The results indicated that the simulation modeling could adequately determine strength at a deflection of 1/360 of the span. The ratio of difference between the experimental results and the simulation modeling results was less than 10% if a dowel connection at the web was applied. However, the ratio of difference reached 26% and 24% in the TSC beams without a dowel connection at the web that were fastened with screws and nails at the flange, respectively, revealing the importance of applying a dowel connection at the web. Moreover, the strength of the TSC beams with a dowel connection at the web that were fastened by screws was approximately 15% higher than that of TSC beams without screw fasteners. In conclusion, the proposed simulation modeling can provide designers with a method for estimating the initial stiffness and strength of TSC beams within a deflection of 1/360 of the span, supporting the future application of TSC beams in construction.