I think you would be correct to take the word condos out of all of your lower level pages, Providing your top level page has 'condos'. The shorter the URL the better and having condos repeated when a search bot would know it has gone into the condos category already would not add any value.
Having the same URL structure after your top level page is fine as it is within a different category. If it is the exact same page however, make sure your canonicals are correct and functional.
There are many ways you can use internal anchor text. I do agree that you shouldn't have the same anchor text pointing to different pages when you are linking from the main body text, but in a navigation menu it is fine. If I had my choice based on the structure above I might do it something like Home > Condos > Island > City > Region > Neighbourhood. That is purely at matter of preference as it would allow for a good cornerstone top level Condos page to rank well and link to.