The oldest document identified so far regarding the Gypsy Monastery dates from August 1, 1776, from the time of the first reign of Alexandru Ipsilanti. It is a deed of sale of Paraschiv Căplescu, by which the Șigăneşti estate in the Ilfov district is given for sale "to his holiness father Hrisant the abbot".
This act, which offered a place for a monastery to an abbot, attests to the fact that at that time there was already a monastic settlement here, most likely a hermitage, the place then being appropriate for hermit life.
Until 1780, the hermitage was inhabited by monks. From 1805, starting on June 7 of that year, on the initiative of Metropolitan Dositei, monks from the Turbati-Ilfov (near Snagov) and Hagi Dima (Mothers' Hermitage, from Bucharest) hermitages were brought to Șigăneşti, and the monks moved at the Caldăruşani Monastery. We learn about these moves from a charter given on May 5, 1813 by Ioan Gheorghe Caragea, a document that reinforces the rules of monastic life and the decrees made by his predecessor Constantin Ipsilanti.
The reason for the move - as mentioned in the document - was the "large number of people" who gathered at the two hermitages and the fact that "not a little scandal is caused to the nuns". As a result, it is decided that "the said two hermitages with all their movable and immovable properties should pass to the ţigăneşti hermitage". The new establishment is given "under the spiritual guidance and guidance of the abbot from the holy Căldăruşani monastery".
By joining the two hermitages, the monastery acquires greater importance, the community grows, a fact that requires the construction of a more capacious church. In 1812, with the help of Banu Radu Golescu, Logofăt Florescu and Archimandrite Dosita, the then abbot of the Căldărușani Monastery, the church that we can still see today, dedicated to the Dormition of the Virgin Mary, was built in place of the wooden church.
In 1817, the church of the cemetery, dedicated to the Holy Trinity and the hospital, were built by the church preacher Niculae Bâţcoveanu. For the maintenance of the hospital, Bâţcoveanu gives the Zădăriciu estate, from Vlaşca County, to the monastery. The law regarding the secularization of monastic assets from 1863 finds the Gypsy Monastery with numerous possessions: eight estates or strings of estates, seven vineyards (41 pogonas), nine inns, two mills, over 1,500 head of cattle, etc. From all of this, he was initially given the surrounding gardens, 246 pogons for the Ciolpani estate, three vineyards and a few animals. Gradually, however, the effects of secularization are felt, the lands and assets are taken, and the monastery goes to the state budget. After 1864, the subsidy given by the state for food becomes insufficient, the lack of any possessions and material possibilities leads to the economic decay of the monastery.
From an order of the Ministry of Cults, it is found that the bread that was served at the table of the nuns in Șiganesti, in 1864, being made from old and mixed flour, was so black and bad that even the cattle could not eat it, the minister himself, outraged by this state of affairs, he orders that "Bucharest jimbla" be served at the table. The perspective of a better life leads the living to demand the abolition of communal life and the common table; after the intervention of the abbess, the Metropolis approves this decision starting from April 1, 1882.
Now the Gypsy Monastery is an idiorhythmic monastery, with a life of its own. The abbot's building, which was built in 1817, but which, like the other buildings, has undergone several repairs, renovations and improvements, the last in the period 1967-1987, is part of its ensemble. It was also then that the refectory and the infirmary were erected. The old cells of the nuns also date from the same period, but their current appearance is due to the last repairs, from 1987. In 1923, a carpet workshop was established, installed in the space where the hospital used to be. He had 12 looms for working Persian carpets, Smyrna and rugs.
At the beginning of 1959, with Decree 410 regarding the dissolution of some monasteries and the reduction of the number of monks, the nuns were kicked out of the Faculty of Theology and the Monastic Seminaries and expelled from the monastery. Gradually, perhaps thanks to the workshops here, which supplied various church fabrics and ensured the needs of several places of worship, the nuns returned to the monastery, and after 1990 nothing from the outside disturbed the life of the Gypsy Monastery in this way.