This chapter explores the architectural evolution of monastic settlements, tracing their development from their early beginnings in Late Antiquity to their eventual institutionalisation within the Christian Church. It examines the diverse forms of monastic architecture, ranging from isolated hermitic dwellings to large coenobitic monasteries, and the various factors that influenced their design. Providing a broad perspective on monastic life across regions such as Egypt, Palestine, Syria, Sinai, Nubia and Western Europe, the chapter argues that monastic architecture evolved in response to practical, spiritual and defensive needs. It highlights how early anchorites lived in secluded hermitages, often repurposing tombs and quarries, while later monastic communities adopted structured compounds featuring churches, refectories and defensive towers. Regional adaptations also played a key role, with fortified monasteries in Sinai, laurae and coenobia in Palestine, and the impact of pilgrimage shaping settlement patterns. Ultimately, the chapter demonstrates how monasteries functioned as economic centres, pilgrimage hubs and defensive structures. It also underscores how archaeological evidence challenges traditional textual narratives, revealing a more complex and pragmatic monastic lifestyle than literary sources often suggest.