The intensive agriculture that is used in many countries has led to a reduction in biodiversity and the deterioration of the environment. Therefore, it is important to increase the adoption of cropping systems with high biodiversity. The objectives of the present study were the following: 1. assess the performance and sustainability of novel highly diversified production systems compared to the current traditional system and 2. provide quantitative economic and ecosystem service information for farmers, extension workers, and policy makers in order to support the development of sustainable and resilient high species cultivar/landrace diversification (HSD) production systems. The rotation of wheat–pea–barley was a system with low energy inputs and high outputs, significantly increasing the energy efficiency. Also, the same system demonstrated better economic and environmental indices, making it a suitable cropping system for Mediterranean areas.