This article examines the development of charitable activity in the city of Vilnius and elsewhere in the Grand Duchy of Lithuania before the middle of the sixteenth century by studying the foundation of almshouses to care for the poor and destitute and foster the memory and salvation of pious benefactors. Almshouse foundations developed from increasing forms of practical piety within the GDL from the late fifteenth century, following earlier west European and Polish models. The first, dedicated to traditional patrons of such institutions, St Job and St Mary Magdalene, was founded by a Vilnius canon and medical doctor, Martin of Duszniki with the support of the monarch, Sigismund the Old, and his counsellors between 1518 and 1522. The almshouse swiftly became an established part of the city’s sacral topography. The fashion was adopted by Eastern Orthodox parishes in Vilnius too, and later spread to other confessional groups. Twelve charters are published for the first time in an appendix.