Cross-Laminated Timber (CLT) is an engineered wood product made by laminating dimensional or structural composite lumber in alternating orthogonal layers. Compared to Canada and Europe, CLT is a novel product to the US. With the additions included in the 2021 International Building Code (IBC), CLT material properties, especially rolling shear, would need to be explored. The increasing demand for softwood lumber, along with the increase of demand of CLT panel production, could place a burden and surpass the domestic softwood supply. Rolling shear is a phenomenon that occurs when the wood fibers in the cross-layers roll over each other because of the shearing forces acting upon a CLT panel when it is loaded out-of-plane. This study used the two-plate shear test from ASTM D2718 to measure the rolling shear properties of various southeastern US wood species: southern pine, yellow-poplar, and soft maple. A secondary study was conducted, using the same two-plate shear test, to measure the rolling shear properties of re-manufactured southern pine for CLT cross-layer application. The soft maple had the greatest average rolling shear strength at 5.93 N/mm2 and southern pine had the lowest average rolling shear strength at 2.51 N/mm2. Using a single factor analysis of variance (ANOVA), the rolling shear strength values from soft maple were significantly greater than yellow-poplar, which was significantly greater than the southern pine. For the rolling shear modulus, the southern pine and soft maple were of equal statistically significant difference, and both were greater statistically significant different compared to the yellow-poplar. The most common failure found from testing was rolling shear.