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I used to think that the Brits said 'in [determiner] street' whereas the Americans use 'on [determiner] street'. I believe that's what I was taught in school. However, the other day I checked a few dictionaries and didn't found information about such a distinction but noticed both usages. So, what's the truth? Here are some example sentences from Longman.

I bought this coat at a shop on the high street. [it says it's BrE usage]

They live on Clay Street.

on the other hand

The restaurant is tucked away in a side street.

She had lived in the same street in London all her life.

(from here)

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"On" a street is quite normal and correct in British English and American English

Your first example is marked "British" because of the use of "the high street" (or High Street, the proper name of the central shopping street in many British towns and used generally to mean "the shops in the centre of town")

The final examples don't use the name of a street. I'd be happy with "on" for both of them. But "in" is acceptable too.

We would tend to say "In a back alley" which leads to "in a side street", and "lived in...." is perhaps a strong enough colloation that it makes "Lived in the same street" seem quite correct.

I don' think that there is a strong dialect difference here. Both tend to use "on" with streets.

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    This is a really common example that gets used to demonstrate prepositions and how complicated they are (at an address on a street in a town). I think generally on is used for the general address where something is located (the high street can be more of a conceptual place!) whereas in is more of a literal, physical description. To me in the street sounds like you're literally positioned in the road or on the pavement, "in a back alley" gives a sense of having to go into the alley to get to the shop, and makes it feel less like a "normal" address (unlike "side street")
    – cactustictacs
    Commented Jan 3, 2021 at 14:15

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