Located at the very heart of the once divided city, the border crossing between then-communist East and democratic West was famously the scene of a dramatic stand-off between Soviet and American tanks in October 1961.
Since German reunification in 1990 it has welcomed thousands of visitors per day to a bewildering hotch-potch of private and public museums and memorials.
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Widely derided by Berliners as a “historical Disneyland”, the attraction also has problems with overcrowding and hustling of tourists.
In November, the local authorities cracked down on actors dressed as US soldiers posing for selfies, in response to reports of aggressive touting.
Now plans drawn up in consultation with Berlin residents would replace the chaos with a public square, a Cold War museum and a residential block with around 300 new apartments.
“With the involvement of citizens, tracks have been laid for a future-oriented development for this special place,” said Berlin's urban development senator Katrin Lompscher in a statement on Tuesday.
While there is little love for the landmark in its current form, plans to redevelop the 1.3 hectare site have stirred controversy.
The city-state government took control of the process last December, effectively rejecting plans from a local developer to build office spaces and open a Hard Rock hotel near the site.
Since then, Left party politician Lompscher's plans have faced criticism in turn.
Music producer and former Berlin culture senator Tim Renner suggested installing two tanks at the site to memorialize the 1961 stand-off.
Meanwhile the ruling left-of-centre coalition is divided over whether to allow construction of skyscrapers at the site.
Debate over whether to expand upwards echoes battles over Berlin's housing supply that have made headlines across Germany and beyond.
Pressure on accommodation has soared as the population has grown by tens of thousands annually over recent years.
In 2019, the senate has introduced harsh rent controls and bought back thousands of former social housing units from the private sector.
“I'm happy to scare off some investors” who stand accused of profiteering from the living space squeeze, Lompscher said earlier this year.
Despite differences over Checkpoint Charlie, the executive rubber-stamped the plan for fear of allowing the private sector free rein when a temporary development freeze on the site expires early next year.
Berlin's parliament is expected to vote the scheme through before February, but it remains unclear when work will start on the redevelopment.