Numerical modelling of masonry is important in understanding masonry behaviour, especially with masonry having many material and structural variations. Masonry is a heterogeneous material and some finite element analysis (FEA), and discrete element method (DEM) modelling approaches have been able to acknowledge the nonlinear nature of masonry behaviour. This has largely been shown in block-based and element-based models where unit displacements and unit-mortar interface failure have been represented. Despite this, modelling of fragmentation, and mass deformation of units alongside mortar, which is commonplace in masonry deterioration and failure modes has been under-represented. To address this issue, particle-based DEM could provide the desired solution. Previous research has shown that the use of particle-based DEM can prove to be advantageous in accurately replicating the fracture behaviour of brittle materials, crack propagation as well as replicating mass deformation in failure modes by accounting for the behaviour of individual particles at the grain-scale. With the increase in aging infrastructure in today’s world, the demand for advanced non-linear and non-destructive masonry analyses is growing. Parametric studies conducted in this research, which relate particle-based DEM micro-parameters with material properties have been documented, and trends are compared with literature findings. Principles from particle-based DEM literature were applied to create a simple stack-bonded masonry prism model to assess the feasibility of using this analytical technique for investigating the behaviour of various masonry strength combinations when subjected to compressive loading. This model is planned to be developed further to be used to investigate the impact of different geometric and microstructural masonry features on masonry behaviour subject to various mechanical loading scenarios.