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Smallest street bike I've actually ridden on the road (sometime back in the '80s) was a Honda XL250R enduro.
Smallest motorcycle I've owned is a beat '82 Honda Z50R purchased in '99 for my then 4 y/o son to learn on. Younger boy started on it also. Still have it. We've bought and sold others since then, but the boys want to keep the Z.
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