The Monk Alexander of Oshevensk was born on 17 March 1427, 80 versts from Belozersk in the Vysheozersk region, several months before the death of the Monk Kirill of Belozersk (+ 9 July 1427), – with whom he was bound together by later spiritual connections for his whole life.
Alexei (worldly name of the Monk Alexander of Oshevensk) was the fifth son of the rich landowner Nikifor Osheven and his spouse Fotinia; he was a long-awaited child and was born through the fervent prayers of Fotinia. The Mother of God Herself together with the Monk Kirill of Belozersk appeared to her and promised the birth of a son through the intercession of the Monk Kirill. Although Alexei was the youngest son, his parents hoped to see in him their successor and someone to care for them in their old age. In childhood they taught the boy his letters and spoke of him as an enterprising landowner. At 18 years of age they sought to marry off the youth. With the permission of his parents, he went off to pray at the Kirillo-Belozersk monastery and remained there.
The hegumen loved the youth for his humility and soon suggested to him to take monastic vows. But Alexei refused, having decided to test himself. Having studied Holy Scripture, he served the brethren as a novice for six years and only then did he accept monastic vows.
During this time his parents settled in the village of Volosovo, – 30 versts from Kargopol near the River Onega. Soon Nikifor sought of the Novgorod boyar Ioann a place for settling near the River Churiuga, which received the town-name Oshevensk.
The Monk Alexander asked of the hegumen permission to receive from his parents their final blessing and forgiveness, so that afterwards he might go into a solitary life. Not at once did the hegumen give permission to the young monk. He warned him about the dangers of wilderness life. But the Monk Alexander feared the ascetic fame that he had among the brethren, and he requested a second time to be released from the monastery. Finally, the hegumen gave his blessing.
Greeting him with joy, the father suggested to the son that he settle at the River Churiuga and promised to assist in the building of a monastery. The Monk Alexander took a liking to the place. He set up a cross as foundation of the future monastery and gave a vow to dwell there until the end of his life. After this the Monk Alexander returned to the Kirillo-Belozersk monastery and for some time he did obedience in the choir, in the kitchen and in the bakery. They ordained him to the dignity of deacon. Finally, when the Monk Alexander went to the hegumen for the third time and told him, how a miraculous voice had called him to organise a monastery, and how he had vowed to dwell at that place, the hegumen released him, – blessing him with the icons of the Hodegetria Mother of God and Sainted Nicholas the Wonderworker.
The Monk Alexander dedicated the chosen spot with the icons, and received from his father supervision for building a church, and he himself set off to the Archbishop of Novgorod Jona (1459-1470). Archbishop Jona ordained him to the dignity of presbyter and appointed him hegumen of the monastery. The boyarina Anastasia and her son Yurii were prepared to offer the monastery the whole district, but the Monk Alexander accepted the gramota (deed) for only the necessary ground. The constructed church was dedicated in the name of Sainted Nicholas. With determination and energy the monk began to work at organising the monastery. An elder, who had accompanied him from the Kirillo-Belozersk monastery, was not able to endure the harsh wilderness life and went back. By little by little brethren gathered. The monk enacted a strict ustav (rule) of common life, which required complete silence in temple and at refectory, – when saint-lives were read, in monk cells there was to be no idleness, and at the time of fulfilling obediences it was necessary to do the Jesus Prayer or read psalms. "Brethren, – said the monastic hegumen, – let us not shirk work nor the way of sorrow. Ye know, that the way of sorrow leads to the Heavenly Kingdom. Live in mutual love and humility. God is love, and He loveth the humble".
Many even from the layfolk came to the monk and put themselves under his spiritual guidance. Two nephews of the saint accepted monastic orders at his monastery, who offended one of the brethren, – the monk Ambrosii. The Monk Alexander gently calmed the religious brother, but the nephews cooled in their zeal for asceticism and they left the monastery. Grief over the salvation of his spiritual children wrecked the health of the monk. He lay down and was not able to life up his hand nor his head, nor even to utter a word. In such a state of exhaustion the Monk Alexander prayed to the Monk Kirill, his patron. The Monk Kirill appeared in a white robe and, signing the sick man with the sign of the cross, he said: "Grieve not, brother! I intercede and thou shalt be well. Only forget not thy vow, nor leave this place. I shall assist thee". Having fallen asleep, the monk regained his strength and in the morning went to church. To encourage the brethren he told about the visit of the Monk Kirill. The monk laboured for 27 years in the monastery founded by him, and died peacefully on 20 April 1479.
After the death of the hegumen, the monastery began quickly to go into decline. But the monk did not cease to care for it. One time, the monastic attendant Mark had a vision in a dream: the monastery was full of people; a grey-haired elder in bishop's garb signed with a cross those working on the building. Another elder, with a long beard, sprinkled with holy-water; and a third, of moderate stature and blond hair, censed. A fourth one, a youth, followed after them at a distance. The third elder, – this was the Monk Alexander Oshevensk – explained, that Sainted Nicholas the Wonderworker and the Monk Kirill of Belozersk assisted him, and the youth standing at the distance was the cantor Matfei, who was soon vowed under the name Maxim and chosen hegumen of the monastery, as predicted in the vision of the Monk Alexander. The monk Maxim was established as hegumen by the Archbishop of Novgorod Sergei (1483-1485), and he restored the monastery. He was the monastic head until 1525.
At the time of building of a new temple in the name of Sainted Nicholas, during an appearance of the Monk Alexander and at his command, – his relics were found undecayed. His image was then painted in accord with how he appeared as a monk and in accord with the accounts of those who knew the elder: the Monk Alexander of Oshevensk was of moderate stature, with parched face and sunken cheeks, with a small thin beard, grizzled with blond hairs. He is thus depicted on icons.