Aggregated analyses of the benefits from ecosystem services (ES) to well-being neglect important differences among beneficiaries and fail to capture the complexity of factors that mediate the ES–well-being relationship. Based on 25 group interviews, we disaggregated the ES–well-being relationships across six groups of potential beneficiaries in a farming landscape in central Romania, Eastern Europe. We explored what mediates distributional patterns of needs and benefits among beneficiaries and identified six contextual factors: (1) characteristics of the appropriated ES; (2) policies, formal institutions, and markets; (3) social and power relations, and informal institutions; (4) household decisions and individual contexts; (5) different perceptions and understandings of equity; and (6) individually held values. Based on these empirically derived factors, we developed a conceptual model of mediating factors that holistically takes into account the contextual space between ES and human beneficiaries. This model provides a framework for unpacking ES–well-being relationships that may guide ES research across varying socioeconomic cases. Notably, this model of mediating factors incorporates an equity perspective that is more refined than the dominant discourse on the relation between poverty and ES (which typically emphasizes that poor people are most dependent on ES, but neglects factors such as power relations and held values). Recognizing multiple contextual factors that shape the contribution of ES to well-being opens doors for harnessing new interdisciplinary collaborations and can help to inform more holistic policy interventions.