Known since 1837, this street led from Kontraktova Square to Obolonskiy Luky and connected with the road to Vyshgorod. Over the years of its existence, it changed its name several times. The street received its current name in 1869 in honor of the church of Constantine and Helena, which was located nearby and was destroyed in 1930.

The architecture of Kostyantynivska Street, as well as Podol in general, is characterized by the fact that the oldest buildings stand at the beginning of the street, closer to Kontraktova Square, and further, to the north of Shchekavytska Street, buildings from the second half of the 20th century dominate. Among the monuments associated with the street are the Guest Courtyard, the Samson Fountain, and the estate of the Kyiv voyt Yan Bykovsky.

Since 1891, a tram line has been running along Kostyantynivska Street — first horse-drawn, and since 1894, electric, connecting Podil with Kurenivka and Pushcha-Vodytsa.