The Portuguese eremitical congregation of São Paulo in Serra de Ossa was founded in 1482, combining a large number of eremitical settlements – documented since 1366, mostly in the Alentejo region – under a centralized government. In 1578, an autonomous congregation was set up, and became then affiliated with the Hungarian Order of Saint Paul the First Hermit, until the extinction due to the decree of dissolution of the religious orders in 1834. The research analyses the material aspects regarding the congregation’s settlements – the architectural and landscape features – with the aim at complementing previous researches in the field of medieval history. The study examines the genesis of the “homens da pobre vida” movement and the spatial distribution of its communities in the Portuguese territory, comparing it to other religious movements in order to understand the reason of such a density in the Alentejo region. On the other hand, it provides a reconstruction of the late medieval settlements from historical documentation – mostly charters – aiming to define the eremitical landscape. After the settlement’s identification, a census of the existing physical structures – sometimes just evidences – was carried out. The seventeen monastic settlements, forming the eremitical congregation, are examined at a micro-scale, through a literature review, an archival dataset, and an on-site spatial and morphological analysis, towards the formulation of a typological definition. This research intends to outline a multidisciplinary methodology, crossing the fields of history, archaeology, architecture and heritage. Being quite ambitious, in terms of geographical and chronological range, it intends to trace new paths and possibilities for future studies, which could establish comparisons between this and other religious orders. The findings of the analysis highlight a continuity in the communities’ choices of location, strategy of occupation, architectural function and spatial organisation.

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