Yeah, I guess it depends. I worked in that area for five years from 2018-2023 and the worst that’s happened to me on that street was being cat-called. Boston Police are usually monitoring all over that area, too. Just be smart and you shouldn’t have any problems.

It’s pretty rough in the sense that there are homeless addicts, but people usually don’t bother you unless you bother them. I walked those streets to the T at night alone as a female student for years and never had an issue. I did carry pepper spray on me, but never had to use it. Just be smart and aware of your surroundings. There is also no parking on Winter Street, not even street parking, so I assume you would be parking on Tremont or elsewhere. Just FYI

I was already thinking Southie before I even read that you were working there. Based on the fact that you are working there too, I would absolutely live in Southie or the South End (yes they are different). Brookline is great, but if you're working in the office 5 days a week I think you'd hate that commute. Cambridge would be doable as it is on the red line.