Sir Walter Raleigh, one of the great figures of Elizabethan-era trans-Atlantic history, was granted a substantial estate in Ireland during the Munster plantation of the late sixteenth century. Although he was appointed its mayor in 1589–90, he spent relatively little time in the port-town of Youghal, the principal urban settlement in his grant and the gateway to his inland estate. The free-standing house known as Myrtle Grove, which is still occupied, is popularly identified as having been his residence in Youghal. However, an evaluation of the documentary and cartographic evidence for properties in the late sixteenth- and early seventeenth-century town indicates that he could not have lived in it, although he probably lived very briefly near it. The reinterpretation of the buildings and topography of the corner of Youghal where Myrtle Grove is located illuminates how, at the start of the period of England’s Atlantic colonialism, the ancient town metaphorically straddled two worlds, the “old” and the “new,” and two periods, the medieval and the modern.