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Try asking for Peachtree Road in Atlanta major. There are no fewer than 20 variants of Peachtree (Road, lane, drive, Corners, etc).

Boston has at least two Glen Roads, differentiated only by neighborhood and ZIP code. I found this out when a friend drove up to visit, called, and asked: "Do you live in some kind of gated community?!"

"No."

"I didn't think so."

Next to Greenwich Park, there's Vanbrugh Park, Vanbrugh Park Road, Vanbrugh Park Road West, Vanbrugh Fields, and Vanbrugh Hill all in ~100m radius.

Also Vanbrugh Castle as a house name within the same radius but, obviously, isn't on any of the aforementioned roads.

The one that gets me every time is Parkmoore and Moorepark on opposite sides of 280 in San Jose. I be someone thought they were being clever when they named them.

In Chicago, Wacker Drive has an Upper and Lower, goes North, South, East, and West, and crosses itself 6 times. Confusing for people who aren't familiar with it!