© 2021 by the authors. Licensee MDPI, Basel, Switzerland.The majority of architectural heritage consists of load-bearing masonry components made up of stone units and relatively weak mortar joints, yielding potential weak planes for masonry structures where tension and shear failures are expected to occur. Advanced nonlinear analyses are required to simulate these phenomena and predict the corresponding nonlinear structural behavior of historic masonry constructions. In this context, this paper presents a model of a stone masonry Roman aqueduct (the Valens Aqueduct), constructed in the fourth century A.D. in Istanbul, Turkey, to explore the seismic capacity and behavior using the discrete element method (DEM). The employed modeling approach comprises distinct rigid blocks interacting along their boundaries based on the point-contact hypothesis. Thus, the discontinuous stone skeleton of the masonry aqueduct is represented explicitly in the computational model. First, a validation study was conducted on the laboratory experiment to demonstrate the capabilities of the adopted modeling approach. Then, a discontinuum model representing the Valens Aqueduct was used to assess the seismic capacity of the structure under gradually increasing lateral forces. The numerical simulations gave insight into the structural response of the aqueduct from the elastic range to total collapse. Additionally, parametric research was performed considering joint properties, namely the joint tensile strength, contact stiffness, joint friction angle, and compressive strength of the masonry, to quantify the effects of contact parameters on the displacement response of the DEM model. Further inferences were made regarding the modeling parameters, and practical conclusions were derived.