1. Traditional wood-pastures are emblematic of multifunctional farming systems. Despite their exceptional ecological and cultural value, these systems are undergoing rapid transformation under the combined pressures of modernization, land-use intensification and shifting societal values. 2. We apply the Stephenson's Cultural Values Model to assess the biocultural complexity of 110 ancient wood-pastures across Transylvania, Romania, a unique region of Eastern Europe, where traditional land-use systems persist amidst accelerating institutional and economic change. The three dimensions of the Cultural Values Model—‘Forms’ (material structures), ‘Practices’ (land-use activities) and ‘Relationships’ (cultural meanings and memories)—were quantified through field surveys and 32 semi-structured interviews with local stakeholders. 3. Our results reveal diverse biocultural profiles, with traditional and modern elements (i.e. ‘Forms’ and ‘Practices’) frequently co-occurring. While many sites retain legacy features such as scattered veteran trees and extensive grazing, signs of social-ecological reconfiguration are evident, including electric fencing, mechanized infrastructure, and declining communal governance. Landscape-level analyses show that traditional features (‘Forms’, ‘Practices’ in the Cultural Values Model framework) persist more often in rugged terrains, whereas modernization predominates in flatter, more accessible areas. Interview data show an erosion of cultural engagement, stewardship norms and local agency. 4. Our findings suggest that the transformation of ancient wood-pastures can be effectively traced through the three pillars of the Cultural Values Model: ‘Forms’, ‘Practices’ and ‘Relationships’. The framework proved especially valuable in disentangling how material, functional and symbolic dimensions of these landscapes evolve in response to socio-economic and institutional pressures. We also showed that the Cultural Values Model can be a practical tool for assessing biocultural complexity and identifying early signs of system reconfiguration of traditional farming systems.