The paper discusses a captivating, though understudied Florentine double-sided portrait of a young woman, whose name has been recently identified by the present author as ‘Maddalena’, in the Gemäldegalerie in Berlin. It was painted c. 1490 by Agnolo del Mazziere (formerly known as the ‘Master of Santo Spirito’), and has been frequently published in the scholarly literature, but always with a very summary treatment, rarely exceeding a paragraph. As has been shown here, and contrary to usual assumptions, the painting is not simply the likeness of a young woman with allusions to the ideal virtues of married life. The subject matter, technique of execution, and ulterior messages of the picture raise interesting questions deserving further attention. The painting style and figural form of the Berlin portrait may seem conservative in view of the most innovative artistic currents of the late 1480s and 1490s, and even more so if the picture is compared to Leonardo’s much earlier Ginevra de’ Benci. It is argued here, however, it is the larger and very rich socio-historical context which elevates the Berlin painting to a special documentary significance in the history of art, and it is hoped, in the future, to a more prominent place in the mainstream historical literature and feminist discourse.