@vvlad,
First off, nothing is bolded.
And you can check Google Maps and just put the address in and actually see the building when you switch to Street View. A terraced house is called a row house in a lot of other places. It's attached to other buildings. Cities like San Francisco and Boston have a lot of row houses. It's something of an older style.
The "very top of the house" is
exactly what it sounds like. Whatever is the top floor, that's it. Since someone is living there, it implies at least 1 finished room. But otherwise, there are no contextual clues. It's also not necessarily just 2 floors. It could be more although more than 5 or so and you're probably not talking about a house anymore and more like an apartment building, even a small one.
Stare out of a window implies nothing of the sort. It just means someone is looking, whether the window is open or closed, and whether their head is within the room or not.
I'm assuming you're asking if "like looking at a Monopoly board" is an idiom. It is not. It is
exactly what they are saying, most likely implying that the buildings and streets are laid out in a neat, well-planned grid.
You seem to be overthinking this. Everything here is rather straightforward. Adding complexity where there is none intended is only going to make learning English more difficult.