No, it is not natural English. The example you've stated is an exclamation of surprise. It is a response to someone already saying how long the road is. The question here is asking how long the road is from the perspective of someone who does not know how long the road is. Therefore, they do not mean the same thing.
That example was more of an exclamation, but there are other in-real-life situations in which a native English speaker might phrase a question in that way. E.g. needing to (physically) indicate what road they're asking about or knowing what road they needed to talk about, but figuring out what they need to know about it on the fly (not knowing what they were going to ask in advance). Definitely not textbook, but not that uncommon when we don't know exactly what we're going to ask before we start talking. It does seem like the Korean would be the same in the two examples I listed, which is kinda fun/interesting.