Guided wave propagation has recently drawn significant interest in the ultrasonic characterization of bone. In this work, we present a two-dimensional computational study of ultrasound propagation in healing bones aiming at monitoring the fracture healing process. In particular, we address the effect of fluid loading boundary conditions on the characteristics of guided wave propagation, using both time and time-frequency (t-f) signal analysis techniques, for three study cases. In the first case, the bone was assumed immersed in blood which occupied the semi-infinite spaces of the upper and lower surfaces of the plate. In the second case, the bone model was assumed to have the upper surface loaded by a 2mm thick layer of blood and the lower surface loaded by a semi-infinite fluid with properties close to those of bone marrow. The third case, involves a three-layer model in which the upper surface of the plate was again loaded by a layer of blood, whereas the lower surface was loaded by a 2mm layer of a fluid which simulated bone marrow. The callus tissue was modeled as an inhomogeneous material and fracture healing was simulated as a three-stage process. The results clearly indicate that the application of realistic boundary conditions has a significant effect on the dispersion of guided waves when compared to simplified models in which the bone's surfaces are assumed free.