No written records have yet been found that would indicate when and by whom this settlement was founded. From a Turkish census register from 1519, we learn that by the Bregalnitsa River, at Kaj Novo Selo, there existed a bridge together with the settlement, such as those built by Sultan Bayazit Khan (1389–1402). At that time, the settlement had 21 Christian households.
During the reign of Sultan Murat II (1421–1451), due to Novo Selo’s strategically important position, a ferman was issued declaring it a military and guard settlement, granting it special rights and privileges—to serve as guards, protect the road and the bridges.
As a result of these privileges, already by the beginning of the 18th century Novo Selo became a significant settlement, which was also home to Metropolitan Kir Efrem of Shtip. Such status and the presence of educated people had a strong positive influence on the level of economic, cultural, and political life, reaching its peak in the 20th century, when a large number of wealthy and prominent old families engaged in crafts and trade lived there.
Its topographic position led to the development of three groups of buildings distributed along the slopes of Isar, Kumlachka, and Merite. These groups were connected by two bridges over the two rivers into one indivisible whole. From the first half of the 20th century, Novo Selo is considered to consist only of the two groups of buildings arranged amphitheatrically along Kumlachka and Merite.
At the end of Ottoman rule (1912), Novo Selo had around 700 houses. From then until today, their number has significantly decreased, and the condition of most of the remaining houses is quite poor.
Within the urban settlement, two areas stand out that served as community centers. One is near the church “St. Bogorodica”, and the other is the area known as “Javor”, which overlooks the Bregalnitsa River.
