The article studies gifts of the Sheremetev family to the Kirillo-Belozersky Monastery in the 16th century. It draws on materials of the first Gift book (vkladnaya kniga) of the Kirillo-Belozersky Monastery for 1559/60?1620s and on those of later gift inventory for 1618?40, Commemoration book (kormovaya kniga), acts, and other sources. The Gift book of the Kirillov Monastery 1559/60 ? 1620s was unknown to the author of a fundamental study on the Sheremetev family A. P. Barsukov and other researchers. Meanwhile, its materials clarify some data on the Sheremetevs’ gifts to the Kirillo-Belozersky Monastery and biographies of the members of this family. The Sheremetevs started making their donations to the monastery in late 1540s, when their career at the court began. The first Gift book contains information on donations made “in commemoration of the soul” of Ivan Bolshoi, Grigory, Nikita, and Ivan Menshoi Vasilyevich Sheremetevs. All of them, as well as the son and daughter of Ivan Bolshoi Vasilyevich Sheremetev (Yeremey and Agafya), the son and grandson of Ivan Menshoi Vasilyevich Sheremetev (Fedor Ivanovich and Alexei Fedorovich) were buried in the Kirillo-Belozersky Monastery. The Sheremetevs' donations to the Kirillov Monastery were very rich. Especially large gifts were made by the eldest brother, Ivan Bolshoi Vasilievich, amounting to more than 1,500 rubles. The Gift book provides most accurate information on time and circumstances of the Sheremetevs’ donations to the monastery in the 16th century (in comparison with the Commemoration book and other sources). For example, the materials of the Gift book clarify the date of death of Semen Vasilyevich Sheremetev (October 8, 1557) and that of tonsure of Ivan Bolshoi Vasilyevich Sheremetev in the Kirillov Monastery (shortly after June 6, 1571). The authors note that, despite their successful career and service, the Sheremetevs did not enjoy the favor of Tsar Ivan and were under his suspicion. Therefore, it is the Kirillov Monastery, located far from the political storms of the 16th century and enjoying great prestige as a spiritual center, that the Sheremetevs choose as their family monastery and burial place.