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In this sentence, the difference is clear, I think:

He put on his jacket and ventured into the street(s).

street: one specific street.

streets: the streets of that city/town.

In the following sentence, however, I'm not very sure. Both options seems correct to me:

Let's wait until there are fewer people on the street(s).

Is there any difference? What option is more appropiate?

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    The distinction seems the same as the one you mention in the first part of the question. Are you talking about a specific street, or all the streets?
    – Stuart F
    Aug 18, 2021 at 15:49
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    In my experience as a speaker of AmE, very little consideration is given to differentiating the two words when used as you have used them. Street is often understood to mean Streets. Both are acceptable. I would interpret them both to mean one or more streets. I would only try to differentiate if there was a reason I needed to communicate something that applies to a particular, single street instead of many streets.
    – EllieK
    Aug 18, 2021 at 16:15
  • @StuartF I'm not referring to any particular street.
    – wyc
    Aug 18, 2021 at 16:50

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There is a subtle difference in your two examples and I don't think they mean quite the same thing. Street can be used literally to refer to a paved road. Street can also be used to refer to particular things that that are outdoors or occur outdoors. Here in the U.S. homeless people live on/in the street or streets. You may say either. They both mean out of doors or unsheltered.

If I say He puts on his leather jacket and ventures into the street(s), I would generally be saying ...and ventures outdoors. This is different than saying He went into the street and starting clearing downed trees from last night's storm, which is a literal reference to a paved road.

When referring to literal, paved roads you will want to pay attention to the plural form. The street is covered in oil is different from The streets are covered in oil. When referring to outdoors you can use either street or streets. In that instance they mean the same.

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