The first mention of the church dates back to 1625, but it is believed to have been founded in the late 16th century. Its dedication is likely connected to the coronation of Boris Godunov in 1598, which coincided with the feast day of St. Simeon the Stylite. In memory of this, two churches dedicated to Simeon appeared in Moscow: one beyond the Yauza River and the other in the Povarskaya sloboda. The wooden structure burned down during the Time of Troubles but was soon restored. A stone church was built with treasury funds under the decree of Tsar Feodor Alexeyevich in 1676 and 1679.

The church has a traditional structure: to the west, a wide refectory with two single-domed chapels adjoins a tented bell tower, while to the east is a square body with three altar apses. The main part of the temple is topped with five domes resting on a hill of kokoshniks. Special attention is drawn to the cornice made of bricks set at angles to each other. Several white stone gravestones from the 17th and 18th centuries have been preserved in the southern and northern walls of the church, reminding of the parish cemetery that existed here earlier.

After the stone church was built, only one of the chapels in the refectory was dedicated to St. Simeon, while the main altar of the church was consecrated in honor of the Feast of the Entry of the Most Holy Theotokos into the Temple. Another chapel was originally dedicated to St. Nicholas the Wonderworker, but in 1759 it was re-consecrated in the name of St. Dmitry of Rostov.

The church is known as a place of marriage for many prominent figures in Russian history and culture. In 1816, writer S.T. Aksakov married O.S. Zaplatina here, and in 1866, future Ober-Procurator of the Holy Synod K.P. Pobedonostsev and E.A. Engelhardt. However, the most famous wedding took place here in 1801, when Count N.P. Sheremetev married his serf actress P.I. Zhemchugova-Kovalova. The ceremony was held in secret to avoid scandal due to the 'unequal marriage' among the nobility.

Among the famous parishioners of the Simeon Church was N.V. Gogol, who lived nearby and was communed by the rector of the church before his death in 1852. In the wooden house that stood north of the church until the 1960s, the famous actor P.S. Mochalov lived. In 1829 and 1832, M.Yu. Lermontov lived on Malaya Molchanovka with his grandmother; this house now houses a museum.

In 1938, the Church of St. Simeon the Stylite was closed and slated for demolition. Although these plans were not realized, the building suffered greatly, losing its domes and the tented top of the bell tower. Inside, a carpentry workshop was set up. In 1961 and 1964, during the construction of the New Arbat, the church again faced the threat of demolition, but thanks to the intervention of cultural figures, restoration began. By 1966, the temple regained its historical appearance, but without crosses on the domes, which were restored only in 1990 when the building was returned to the community of believers. Soon, the church was repainted inside, the iconostases of the main temple and chapels were recreated, and services resumed. Today, the Church of St. Simeon the Stylite remains the only one on Povarskaya Street, as all other churches were destroyed in the 20th century. The historical surroundings of the temple have also been almost lost, as it is now surrounded by the New Arbat.