The effect of densification of the laminas was studied relative to the shear performance of cross-laminated timber (CLT) specimens submitted to the bending test. The three-layered CLT panels were fabricated using loblolly pine (Pinus taeda L.). A compression ratio (CR) of 50% was used to densify the lumber using the thermomechanical densification technique. The process included plasticizing the lumbers by soaking them in boiling water for 10 minutes and then hot-pressing to the target thickness at 140 °C. Four groups were made, i.e., a control sample with all three layers non-densified, only mid-layer densified, all layers densified, and all layers planed to the same thickness of densified layers. Specimens were tested in short-span bending with a span-to-depth ratio of eight. For specimens having densified mid-layer, the failure mode changed from rolling shear to tensile failure of the outer layer, and the maximum shear stress was increased by 34%. Densification of the mid-layer at CR of 16% was sufficient to change the failure mode from rolling shear in mid-layer to tensile in outer layer. In the case of all-layer-densified specimens, the maximum rolling shear strength was increased by 129% compared to the control.