The most important historical building on the road, Gothic Revival Petrovsky Palace, was built in 1776–1780 by Matvey Kazakov as the last station of royal journeys from Saint Petersburg to Moscow.

In the 1890s-1900s, the highway was gradually urbanized, with factories and residential quarters, ranging from working-class barracks to luxury country homes of the Morozov family, Nikolay Eichenwald and Fyodor Schechtel.

Leningradsky Prospekt itself is home to the future Dynamo Stadium and CSKA Moscow's winter and basketball arenas.

Since 2005, the city of Moscow is engaged in a multi-billion project of converting Leningradsky arterial, from downtown Tverskaya Street to MKAD, into a 12-lane, non-stop freeway with frontage roads.

Authorities declare the goal is improving transportation to remote districts beyond MKAD and Sheremetyevo Airport, however, the worst bottleneck on the road, in the city of Khimki, is not addressed at all.

Daytime traffic is frequently paralyzed by construction detours, thus the only reliable transportation is through Zamoskvoretskaya Line of Moscow Metro (Belorusskaya to Sokol).