This small convent, located on a steep bank of the Pisma River, is one of the oldest monasteries in the Kostroma region. It was founded in the late 14th century by a disciple of Sergius of Radonezh, the Venerable Makary of Pisma. Unfortunately, the life of the saint has not survived, and very little is known about him. Venerable Makary, whose secular name and date of birth are unknown, came from a Kostroma noble family and was a native of the area by the Pisma River. In his youth, he renounced the privileges of his class and went to the Trinity-Sergius Monastery in the Moscow region, where he was tonsured by Sergius of Radonezh and received the name Makary. After undergoing spiritual training under Sergius's guidance, Makary returned to his homeland with his blessing. He built a cell in the forest on the bank of the Pisma, about a kilometer from the future monastery, and lived in solitude. Later, another disciple of Sergius, the Venerable Pavel Obnorsky, joined him, whom Makary considered his spiritual mentor. They lived together for about 20 years. Around 1389, Pavel went to the Obnora River, where he founded the Trinity Pavel Obnorsky Monastery. A few years later, Makary and his disciples left the 'old wilderness' and built a small church on the bank of the Pisma in honor of the Transfiguration of the Lord, around which the monastery arose. This likely happened in the late 1390s. The exact date of Makary's death is unknown, but it is believed that he passed away in the late first quarter of the 15th century and was buried in the Transfiguration Church.

The revival of the monastery began in the autumn of 1995 at the initiative of Archbishop Alexander of Kostroma and Galich. The monastery was renewed as a women's convent, with Mother Angelina Travina as its abbess. Despite her age, Mother Angelina, possessing energy and resourcefulness, took on the task of reviving the monastery. In a short time, she and the first generation of sisters managed to accomplish much: fully restore the wooden church over the relics of Makary, build living cells, and establish a farm. Bells were installed in the belfry, and the well dug by Makary was put in order. In 2000, the monastery celebrated its 600th anniversary.

In 2004, in addition to ongoing repairs in three churches, two new houses were built at the entrance to the Makaryevo-Pisemsky Monastery, a well for drinking water was drilled, and two ponds for fish breeding were dug. In 2005, five domes and the belfry of the Transfiguration Church were repaired and installed. The monastery is home to 15 residents.