The transition to sustainable energy systems is crucial for reducing carbon emissions and improving energy efficiency in buildings, especially with the growing adoption of photovoltaic (PV) systems and battery energy storage systems (BESS). This study presents a dynamic simulation-based assessment of an integrated PV-BESS system combined with electric vehicle (EV) charging in a single-family dwelling in Southern Italy. Using DesignBuilder and EnergyPlus, a dynamic model was developed integrating real-world climatic data, building geometry, and dynamic user behaviors. The analysis evaluates two PV-BESS configurations and four potential EV charging integration patterns. It compares a shortage configuration (Configuration A) with a surplus configuration (Configuration B), assessing their impacts on self-consumption, grid dependency, economic feasibility, and environmental performance. Configuration A achieves a renewable energy share slightly above 60%, meeting 66% of the dwelling’s energy demand, relying on the grid for 42%, and exporting 8% of surplus electricity. Configuration B meets 120% of the energy demand, reducing grid dependency to 20% but exporting 43% of the generated electricity. The economic assessment, based on life cycle cost (LCC) and payback period (PBP), shows that Configuration A has a lower LCC but an unfeasible PBP. In contrast, Configuration B, despite achieving a viable PBP, would exceed its system lifespan. The environmental analysis highlights Configuration B’s superior sustainability, with an energy return ratio (ERR) 37% higher than that of Configuration A. These findings underscore the trade-offs between energy self-sufficiency, economic viability, and environmental performance, advocating for optimized configurations that support decarbonization and grid resilience in residential contexts.