The macro-modeling approach is widely applied to the analysis of masonry structures. This study investigates the simulation of an irregular unreinforced masonry wall utilizing discrete and continuous homogenized models under varying static loading conditions. The discrete modeling uses the “Joints enriched Finite Element Method (JFEM)” with the cohesive zone model CZFrac for mortar joints, while an elastoplastic hardening/softening model is used to represent the stone blocks’ behavior including their brittle characteristics. The continuous equivalent model is obtained by numerical upscaling methods from the macro stress-strain curves generated for static loads under compression, tension, and shear loading paths. This elastoplastic anisotropic model Anelvip represents the homogenized behavior. It covers the anisotropy of elastic stiffness coefficients and the strength criterion, as well as different hardening/softening properties under compression, traction, and shear loads. It is shown that the homogenized model obtained in this way effectively captures the anisotropic elastoplastic parameters and accurately represents the peak, post-peak, and residual values for various loading patterns and directions and with adequate parameters values, reproduces well the softening or the brittle/ductile trends of the homogenized wall behavior.