This paper presents an experimental and numerical study into the shear response of brick masonry triplet prisms under different levels of precompression, as well as samples reinforced with carbon fiber-reinforced polymer (CFRP) strips. Masonry triplets were constructed with two different mortar mix ratios (1:1:3 and 1:1:5). In this study, finite element models for the analysis of shear triplets are developed using detailed micro-modelling (DMM) approach and validated with the experimental data. The failure mechanisms observed in the masonry triplets were simulated using a coupled XFEM-cohesive behaviour approach in ABAQUS finite element software. The nonlinear behaviour of mortar and brick was simulated using the concrete damaged plasticity (CDP) constitutive laws. The cohesive element with zero thicknesses was employed to simulate the behaviour of the unit–mortar interfaces. The extended finite element method (XFEM) was employed to simulate the crack propagation in the mortar layer without an initial definition of crack location. CFRP strips were simulated by 3D shell elements and connected to masonry elements by an interface model. The changes in failure mechanism and shear strength are calculated for varying types of mortar and fiber orientation of CFRP composite. Based on this study, it was concluded that the ultimate shear strength of masonry triplets is increased due to the external bonding of CFRP strips. The performance of masonry specimens strengthened with CFRP strips is assessed in terms of gain in shear strength and post-peak behaviour for all configurations and types of mortar considered. The comparison of FE and experimental results proved that the models have the potential to be used in practice to accurately predict the shear strength and reflect damage progression in unreinforced and CFRP-reinforced masonry triplets under in-plane loading, including the debonding of the CFRP reinforcement. Additionally, XFEM was found to be a powerful technique to be used for the location of crack initiation and crack propagation in the mortar layer.