There's the Synchronized browsing feature:
https://winscp.net/eng/docs/task_navigate#synchronize_browsing
But if your directory structure is different, it won't work.

I'm using 5.17.5. Is there a way to switch to a specific local folder when I switch folders on the remote server? I have various folders on my remote server, each of which corresponds to a local folder, but the directory structures are different so it's a bit of a pain to have to switch the local folder manually each time. I can't find anything in the docs about this.