In the US, private property isn't very grey. With a few exceptions like ag gag laws (which probably won't hold up to first amendment challenges) or invasion of privacy, you can photograph whatever you want on private property and the only recourse the person who controls that property has is to trespass you.
You mention one thing. Are they trespassing? It probably varies by state anyway, but a photo from public property is almost certainly OK perhaps absent big telephotos peering through windows--though, if you're a celebrity, leaving your shades open in probably on you I would guess.
But, yes, in general, a lot of things in this vein are OK in the US that at least theoretically aren't in some European countries.
I used "trespass" as a transitive verb. It's a remedy, not something the hypothetical photographer is doing. It's when a person who controls a property can demand you leave and not return under penalty of arrest. It's not linked to photography specifically—a person who controls a property can trespass you for virtually any reason or no reason at all. They can't make you delete your photos or anything else. The hypothetical photographer is only trespassing when they've been given notice that they need to leave (i.e. the person who controls the property has trespassed them) and they refuse to do so.
