Kyustendil, where we currently have property for sale, is one of the most ancient towns in Bulgaria. Fertility and the warm mineral springs attracted the Thracian tribes of danteleti and peontsi, which founded here a settlement far back in 5th-4th century BC. During the 1st century the Romans turned it into an important fortress, trade venue and renowned spa resort, calling it Pautalia. In 4th century the fortress Hissarlaka was built later reconstructed by the Byzantine Emperor Justinian I (572-565). After 553 the name Pautalia is not accounted any more. In 1019, in the Charter of the Byzantine Emperor Vassilii II, the town was mentioned by the name Velbuzhd, probably after the name of a leader. It was integrated to the Bulgarian State during the reign of King Kaloyan (1197-1207). From 1379 to 1395 feudal ruler had been Konstantin Dragash and by his name, later in the 16th century, the town was renamed Kyustendil (the land of Konstantin).

From the middle of the 15th century the Turks began to colonise massively the town and subjected the Bulgarian population to assimilation. In the end of the Ottoman domination and after the Liberation, in particular, the ethnic make up changed due to the numerous Bulgarian emigrants from the lands remaining under Ottoman rule and from the neighbouring settlements. During the Revival the town rapidly grew and developed. A church school was opened (1821), its inhabitants took active part in the ecclesiastical and national struggles. The detachments of haidouts (armed volunteers), lead by Ilyo Voivoda and Roumena Voivoda, one of the few women leaders in Bulgarian history, were very active in the surrounding mountains. Kyustendil was liberated on 29th January 1878. After the liberation some of the crafts depending on Turkish markets declined, but tobacco production developed, as well as spa resort activity.