It really depends on the basement. Certain foundations are more prone to flooding. Certain foundations may have mitigation methods installed (French drain systems, etc).

If you're buying a house, a competent home inspector should be able to evaluate for previous water incursion. If you're renting, I'd reach out to the landlord and ask.

Now, certain weather events can cause area-wide flooding. However, the FEMA flood map seems to have Boston Street out of the flood range. https://msc.fema.gov/portal/search?AddressQuery=baltimore%20maryland#searchresultsanchor

It would depend on the basement, as someone already said in the thread here. That being said, 3-4 blocks up from Boston depending on where you are, is O'Donnell or above that, so flooding from storms itself you should be fine on, since that's pretty much uphill from the waterfront.

The basement is weird. On the sidewalk there is 5 stairs up to the front door but underneath the stairs there is another front door to the basement that you can’t really access from the street bc it’s under the stairs and partially below the sidewalk but it seems like all the water on the sidewalk would flow under the stairs and leak through the basement front door. The basement has a back door to a concrete patio as well

Sewer backup might be more of a concern- make sure your homeowner's covers it.

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I live a block north from the Square, and I would say that my partially finished basement can sometimes get a little moist/damp in certain spots when there's a heavy rain, but it's not disastrous or damaging -- just get a good dehumidifier.

It depends on the Basement, generally they don't flood there, but there may be some ground water seeping in. Lakewood is the worst street for that.

As far as water coming down the sidewalk and into the basement door, it's usually not a problem as long as the bottom of the stairs has a drain to your sump. But if it is a problem for heavy rains, it seems like 3-6 sandbags would be an easy solution.

The bottom of those steps should have a drain. Ideally that drain would connect to a French drain system and a sump pump. You need an inspection and you need to ask these questions.

This is very important. My friend learned this the hard way

It really depends on the basement.

My unfinished stone wall basement 1 block from Boston St. regularly got wet during rain. Namely tons of condensation which ran down the walls when it was raining or humid. It always dried out thoroughly in pretty short order.

My next door neighbor’s house had a professionally waterproofed/finished basement that stayed completely dry in similar weather.

The basement never flooded during storms (Isabel, Sandy, etc).