In this paper, a one-sided, in situ method based on the time of flight measurement of ultrasonic waves was described. The primary application of this technique was to non-destructively measure the stiffness properties of isotropic and transversely isotropic materials. The method consists of generating and receiving quasi-longitudinal and quasi-shear waves at different through-thickness propagation angles. First, analytical equations were provided to calculate the ultrasonic wave velocities. Then, an inverse method based on non-linear least square technique was used to calculate the stiffness constants using the ultrasonic wave velocities. Sensitivity analysis was performed by randomly perturbing the velocity data, thus observing the effects of perturbations on the calculated stiffness constants. An improved algorithm was proposed and tested to reduce the effects of random errors. Based on the sensitivity analysis, minimum number of angles required to inversely calculate the stiffness constants were suggested for isotropic and transversely isotropic material. The method was experimentally verified on an isotropic 7050-T7451 aluminum with two different thicknesses and a transversely isotropic composite laminate fabricated using 24 plies of CYCOM 977-2 12 k HTA unidirectional carbon fiber reinforced polymer (CFRP) prepregs. The results demonstrated that this technique is able to accurately measure the material properties of isotropic material. As for the transversely isotropic material, this method was able to accurately measure the material properties if the experimental errors can be reduced to less than 1 %.