Before the Time of Troubles, there was a church dedicated to the Holy Myrrhbearers in Karachev, located in the "ostrozhny osyp". During the time of the impostors, the church, like other churches in the city, was completely destroyed. In the first half of the 17th century, when Karachev was being restored, parishioners built a new wooden church on the same site. In 1740, they erected a single-domed stone church in the name of the Transfiguration of the Lord, with an altar in honor of the Holy Myrrhbearers. A stone monument was installed at the site of the old wooden church, which has survived to this day. Later, a second altar in honor of the Mother of God "Joy of All Who Sorrow" appeared in the church. At the end of the 19th century, due to insufficient capacity and the dilapidation of the church, as well as its distance from the parish, the churchwarden, along with the parishioners, built a new stone three-altar five-domed church in the name of the Transfiguration of the Lord. The construction was overseen by the Karachev merchant Pyotr Ivanovich Ivanov. The church was completed in 1888 and consecrated on October 18 of the same year.

The Transfiguration Church was distinguished by beautiful architecture, was spacious, bright, and equipped with "amosov" heating, making it one of the best in Karachev. In 1896, the construction of a stone bell tower began, which has only been brought to half completion to date. A priest and a psalmist served at the church, and metric books and confession records have been kept since 1805.

In 1903, churchwarden Gerasim Vasilyevich Shemyakov began construction of a new stone building for the church school at his own expense, which had not yet been fully completed. The parish of the Transfiguration Church is one of the oldest in Karachev. Until the beginning of the 19th century, it included the central part of the city and the village of Aksinina.

In 1806, a significant part of the parishioners and the village of Aksinina were separated from the Transfiguration Church to create a new Cathedral parish. Currently, the parish consists of merchants and townspeople from the central part of the city, numbering up to 600 men. The parishioners are known for their diligence and responsiveness to the needs of the church and charitable works. The Transfiguration Church was visited multiple times by the Orlov Archpastors: in June 1885, the church was inspected by His Grace Simeon, on August 27, 1890, it was visited by His Grace Misael, on April 26, 1897, by His Grace Mitrofan, and on April 17, 1903, by His Grace Irinei.

The Transfiguration Church was located near Kazanskaya and was popular among the nobility and officials. It was situated at the corner of the present-day Dzerzhinsky Street, formerly Transfiguration Street, and Lenin Street.

With the arrival of Soviet power, the church was closed. In 1937, its domes and crosses were removed, and the building was converted into a dramatic theater. The theater, with a permanent troupe of professional actors, often toured the cities of Oryol and Bryansk regions.

During the Great Patriotic War, the building of the Transfiguration Church was destroyed.