Wheat (Triticum aestivum subsp. vulgare (Vill.) Thell.) is cultivated across a wide range of environments, where growth habit represents a key mechanism of local adaptation. However, modern varieties often lack key traits for sustainable farming, particularly in organic and low-input systems where stress resilience and resource-use efficiency are critical. In contrast, landraces often show greater yield stability under suboptimal conditions. This study assessed the adaptation of spring and winter landraces across two contrasting seasons in a semiarid Mediterranean climate, focusing on yield components, agronomic traits, yield stability, and technological quality. The effects of growth habit, genotype, and environment on the evaluated traits were analyzed, as well as the relationships between agronomic traits and yield across growth habits and environmental conditions. Winter landraces generally outperformed spring types in terms of yield under favorable agroclimatic conditions, while no significant differences were found under dry and hot conditions-though winter types showed greater yield stability. Yield enhancement strategies varied by environment and growth habit. Under favorable conditions, traits such as increased kernel number, early heading, and shorter height improved winter variety performance. Under stress, vegetative development, spike number, and test weight appeared to be critical for winter wheat adaptation, while spring types with greater biomass, test weight, and earliness tended to perform better. Quality analyses revealed that both growth habits exhibited comparable technological quality. These findings highlight the importance of considering growth habit and environmental context when selecting landraces for Mediterranean farming systems. Finally, several genotypes from both habits demonstrated promising adaptation and stability.