The land on which the monastery is located has belonged to the Polyansky boyars since the 17th century. Makary Artemyevich Polyansky, after whom the pogost and the village of Makarovka are named, served in Moscow and received this land in 1686. In 1700, he moved from Moscow to Saransk, and soon a pogost was established on his lands. In 1702, the Church of Archangel Michael was consecrated, and in 1704, the Cathedral of John the Theologian, which has survived to this day, was built. Around the same time, a fence and two towers were erected. In the 1720s, a bell tower was built, and in the 1800s, the Znamenskaya Church, almost identical in architecture to the Mikhailo-Archangel Church, was constructed.

After the revolution, services ceased, and all buildings except for the Cathedral of John the Theologian and the bell tower were demolished.

Since 1969, restoration work began in Makarovka. In 1987, the villagers, with the support of believers from Lukhivka, Kulikovka, and Soldatsky, managed to transfer the Church of John the Theologian and the bell tower to the parish's administration through Patriarch Pimen. Protopriest Georgy Sakovich was appointed as the rector. In 1991, the Znamenskaya Church was transferred to the Saransk Diocese, and in 1996, the Mikhailo-Archangel Church. The former 'castle' of the Polyanskys became the diocesan administration. In ten years, the pogost returned to the Orthodox people, and in 1994 it became a monastery: by the blessing of Patriarch Alexy II and the decision of Archbishop Varsonofy of Saransk and Mordovia, the male John the Theologian Monastery was opened in Makarovka. Protopriest Maxim Chebotaryov, in monasticism Vladimir, became the abbot.

Over thirty years, restorers have achieved much, including the restoration of the 'castle' and the lost objects of the pogost.

Currently, there are several churches on the monastery grounds:

The Cathedral of John the Theologian is a tall square structure with three rows of windows, on its octagonal roof stand two octagons. A porch with a high staircase and an altar part with a separate dome are attached to the main volume. The height of the square structure is 20 meters, and the total height of the cathedral is 28 meters. This structure was characteristic of Volga churches of the mid-18th century, although in the late 17th century, squares were usually topped with five domes, as seen in the Assumption Cathedral in Ryazan, built by Yakov Bukhvostov. Defensive and civil structures, such as the Sukhariev Tower in Moscow, were built in a similar model at that time.

The cathedral is richly decorated, with the facade ornamentation made from nine types of bricks. The decorations, characteristic of Russian Baroque, combine styles from the late 17th and early 18th centuries, including decorations on the window frames, apses, and octagonal windows of the third tier.

The cathedral is one of the oldest surviving buildings in Mordovia, second only to the Church of John the Theologian in Saransk, built in 1693.

The Znamenskaya Church, built in the 1800s, was meant to replicate the forms of the Mikhailo-Archangel Church but is adjacent to the fence. In the 1930s, it was partially dismantled and restored in the 1970s. Since 1991, services have been held there.

The Mikhailo-Archangel Church, built in 1702, was destroyed in 1935 and returned in 1996.