Not that easily. Even with a fighter at 500 ft above, Mythbusters couldn't break windows. The Oklahoma tests had eight booms a day using very large aircraft. It took months before windows broke.

Long term wear and tear is a legitimate concern.

I’d be pisses if jets flying overheard broke my windows once every five years.

The Space Shuttle's sonic boom broke one of my bay windows when I was living in Orlando. Mythbusters was an entertainment TV show, I wouldn't extend their results to real life.

Especially 100 year + old buildings with original glass.