Settled long ago in the Roman period Middle Polimlje was a part of the oldest Serbian state of Raska. In the first manuscripts, Prijepolje was mentioned as a square of the Mileseva Monastery. It was an agreement from 1343 related to the trade of salt from Dubrovnik to Prijepolje. Prijepolje was developed like a road settlement on caravan's road known as "Dubrovnik's road", which connected central and east part of the Blakans with the middle part of the Adriatic coast. The settlement was one of nodes in the system of Balkan caravans comunication and was in function of the square Merkatum Prepollie and rest areas, where merchants from Dubrovnik resided and caravans departed. Dubrovnik's road passed from Dubrovnik and Kotor via Pljevlja, Prijepolje, upstream the Milesevka valley, towards Mileseva monastery, Sjenica, Ras, Targoviste, Novo Brdo, Pristina, Trepca, Sofia and Constantinopolis. Another important road was "the Bosnian road", which from Dobrun, Bela Brda, Uvac, Priboj, led to Nova Varos and connected to "the Dubrovnik road" in Sjenica. Prijepolje was not only the place of caravan stations, as narrated, but in was much more than that. Merchants were coming and leaving, caravans' arrival and departure broked a new life and the broader points of view of peopl in the region. Therefore, during 16th century, the need to estabilish a caravan-saraja was expressed, facilities for the reception of caravans and accommodation for people. In the 14th century and later, the Lim valley was one of the most important parts of the Serbian lands, Nemanja's state and its descendants. Prijepolje was an important cultural and religious, administrative, economic and transportation centre. Major changes occured in the middle of 15th century, when this teritory and Serbia fell under the Turkish rule. In Turkish times Polimlje losses importance of Stara Raska and its most populous and the most advanced region. Polimlje becomes one of the most backward area of the Turkish Empire. Under the Turkish rule the ethnic structure of Prijepolje changes, beside Christians, Muslims occur. By the end of 19th century on the left banks of the Lim, Austro-Hungarians Empire come and influence of a new civilization and culture was felt in these areas. The development of the town comprises of three main phases: 1. initial-referse to the beginning of village constitution at the intersection of economic and strategically important roads in the location of pre-Slavs settlements, as evidenced by archeorogical finds of Roman necropolis, specially Roman necropolis at the site of the Dvorine in Kolovrat; 2. rural- when it was formed as a settlement, Prijepolje gets rural characters; 3. urban- third decade of the 15th century to the present day gets the status of urban settlement, which is characterized by significant urban developing, which spatial design and structuring starts after the second world war
