The Kaluga Krestovsky Monastery is one of the lost architectural monuments. Only two buildings on Pole Svobody street have survived to this day: a yellow two-story building, the former brotherhood corps, and the former prosfornia.

Originally, a wooden, and later a stone chapel known as the "chapel on Borovskaya road" stood on the site of the Krestovsky Monastery. After a great fire in Kaluga in 1622 that destroyed the city, a revered cross was among the saved relics. The residents decided to place it outside the city on the Moscow road in a chapel to protect this wooded area from frequent attacks at that time. The chapel stood for almost 200 years.

The construction of the Krestovskaya church on the site of the chapel was linked to a specific event. In 1827, retired Colonel P.S. Chebyshev came to Kaluga for treatment and dreamt that he was healed after venerating the Life-Giving Cross in an unfamiliar chapel. During a walk, he accidentally found himself at the Krestovskaya chapel and recognized it. After receiving healing, he decided to build a temple in this place in honor of the Elevation of the Cross. However, two years later, in 1829, Chebyshev passed away. Thanks to the efforts of his wife N.P. Chebysheva and His Grace Bishop Gabriel, the temple was erected within a year and consecrated in 1830. His Grace Bishop Nikolai continued this work, building a stone fence around the church and a wooden wing for the brotherhood. In 1854, His Grace Bishop Gregory erected a two-story stone house with 14 cells and a refectory.

In the 1890s, the church was transformed into a monastery under the administration of the archiepiscopal house. The Church of the Exaltation of the Cross had the shape of an equilateral cross: the western branch consisted of a narthex, the eastern, the altar, the right branch housed the Miraculous Cross, and the left, a chapel in honor of the icon of the Mother of God, the Three-Handed.

The main shrine, the Honorable Life-Giving Cross, was located in the southern part of the temple under a canopy. The cross was octagonal, with a carved image of Christ in full growth, made from solid wood. Nearby was the icon of the Mother of God "Blessed Womb," to which a silver cross with particles of holy relics was attached.

Behind the temple in the garden stood a wooden single-story building on a stone foundation, built for the almshouse. Nobles and merchants were buried around the church, except for the western side. This cemetery was considered privileged. According to the metric books of the monastery, preserved from 1912 to 1917, about 200 people rest in the Krestovsky necropolis, including honorary citizens, nobles, generals, and other notable residents of Kaluga.

With the rise of the Bolsheviks, the destruction of the monastery began. In 1924, the Krestovskaya church was closed, and in the 1930s, the church, bell tower, and fence were dismantled. The field was renamed to Pole Svobody. In 1932, a kindergarten opened in the former brotherhood corps, and later a children's television studio operated here. The prosfornia building was initially a residential house, then a housing management office. Residential buildings and a sports ground for the school now stand on the site of the necropolis.

The fate of the Honorable Life-Giving Cross remains unknown. It is believed that it was destroyed after the decision to demolish the monastery in 1929 when it was deemed worthless.

Since September 2006, work has begun on the restoration of the monastery. In August 2007, an Archiepiscopal residence was established, the Krestovozdvizhensky Men's Monastery in Kaluga, with Hieromonk Tikhon (Shepelenko) as the abbot.

Currently, the buildings of the former brotherhood corps and prosfornia have been transferred to the ownership of the Kaluga Diocese.