Timashovo is first mentioned in the Payment Book of 1621 as a village of the Pyren village council in the Maloyaroslavets district, which belonged to the tsar and was later partially distributed. The village came into the possession of Deacon Lev Dmitrievich Ermolayev, and from 1715 it passed to his son Peter, who managed the estate and 23 peasant households. Peter Lvovich turned out to be a good landlord, and in twenty years the number of households doubled. To obtain the status of a village, Timashovo needed a church. On January 20, 1735, P. L. Ermolayev appealed to the Holy Synod for permission to build a stone church in honor of the Nativity of the Blessed Virgin Mary. By the blessing of the Synod, the abbot of the Maloyaroslavets Chernoostrov Monastery, Igumen Vassian, came to Timashovo to assess the need for the church. On June 13, 1735, a decree for the construction of the church was issued, signed by the Bishop of Kolomna and Kashira, Benjamin.

The construction and decoration of the church with a refectory and bell tower took three years. It was consecrated in late summer 1738 in honor of the Nativity of the Blessed Virgin Mary. Due to the cold building, a decree was issued to create an altar in the refectory for winter time in the name of the holy martyr John the Warrior. The first rector was Priest Fyodor Ivanov.

Since 1782, the village of Timashovo was owned by Peter Alexandrovich Boldin. From 1802, the priest was Irodion Andreev. The State Archive of the Kaluga Region preserves a description of the church's decoration from 1802. The altar was separated from the parishioners' area by a high five-tiered iconostasis. The church housed a copy of the Bogolyubskaya icon of the Mother of God, whose veneration increased after the plague of 1771.

The postal road from Moscow to Kaluga through Borovsk and Maloyaroslavets was opened in 1800. In 1812, Napoleon's troops passed through Timashovo along this road. In December 1812, a report to the Kaluga Spiritual Consistory stated that the Church of the Nativity of the Virgin had been looted and burned. For a year, there were no services in the church, but a year later it resumed its activities. The rector became Priest Peter Fedorov.

After the death of P. A. Boldin, his mother E. G. Boldina managed the estate, who in 1824 rebuilt the altar of the martyr John the Warrior in the style of mature classicism. An antimins consecrated in 1824 and signed by Bishop Philaret is kept in the Kaluga State United Local History Museum. Later, the antimins was replaced with a new one, and the old one was sent to the Kaluga archbishop's sacristy.

According to a report on the parish from 1830, the clergy of the church consisted of a priest, a deacon, and a sacristan. From 1831, the rector became Ivan Alexeyevich Belyaev, while Peter Fedorov remained under the care of his son-in-law. In 1840, the church baptized Ilarion Pryanishnikov, who became a famous artist. From 1874, the rector was Alexander Ivanovich Lyubimov.

In June 1891, Timashovo was visited by Bishop Vitaly, who recommended contacting benefactor Afanasy Petrovich Markov to restore the church. Thanks to Markov, the church was adorned with paintings. After the death of Alexander Lyubimov, the rector became Ioann Fyodorovich Zertsalo, and in 1903, Fyodor Filippovich Stelliferovsky.

In 1938, the church was closed but not destroyed. During the German occupation, the building was used for keeping horses and prisoners. In 1949, Priest Fyodor Stelliferovsky died and was buried opposite the altar. In 1953, the church was turned into a warehouse, and in the 1960s, the iconostasis was destroyed. In 1999, the vault in the refectory collapsed.

On June 30, 2002, on the feast of the Holy Trinity, a water blessing service was held, opening a new chapter in the history of the church. Restoration began in 2002. From spring 2003, the parish was served by Priest Fyodor, and on October 14, 2003, Antoniy Somik became the rector. On September 21, 2004, the first Divine Liturgy was celebrated, and since then the church has continued its ministry.