I don't know how to fix the roof. Someone here will know and give you good advice.

But take those shutters off. They really don't belong at all on your size windows for that house.

Can you shoot a photo of the entire front without doing a panoramic? That way we can get a better idea.

For some reason it reminds me a little of a modern type house - probably because of the way the roof dives into the wall like the pic below.

Modern and Contemporary Home Renovation | Lexington, Ma · More Info

Tilt the addition's roof in the same direction as the rest of the house. It will have to be lifted up to the same level in the front or higher so that it comes down at a reasonable level in the back. Make yourself a google sketchup plan or cut out some foamcore to experiment before you talk to an architect.

I don't think the addition's roof tilt looks bad as it is, but I would worry about water collecting there where meets the other roof (if it even rains there).

Is that white door on the addition the front door? Does the rest of the house have a flat roof? Can't tell it looks like you peiced 2 pics together for the 1st photo

The photos are taken from Google Street View, two different angles. The white door on the addition is the front door.

Interesting to hear feedback that the roof tilt doesn't look so bad to some. That's where my confidence as a 'designer' is so low. I wouldn't have the confidence to leave that kind of an element without some feedback. But if the elevation could be improved substantially *without* changing the roof line, I would definitely prefer that. I'm well experienced in selling houses, but not confident in design. I know that first impression as people drive up is extremely powerful and so has an outsize impact on value. That's where the fix-and-flippers make their money. Make it appeal in and out.

I might explore leaving that roof tilt in place. Maybe add some elements to break up the elevation? It seems that front door is in an awkward place, too.

I do think you can leave that roof line the way it is. If you take a look at that inspiration pic I posted earlier you can see that that roof also 'dives' into a wall, similar to yours, not exactly the same. Here is another view of the same house

Modern and Contemporary Home Renovation | Lexington, Ma · More Info

Some of the treatments they did with the contrasting fascia board and windows are deliberate and attractive. I think if you scroll through houzz you can find modern homes to amp up your curb appeal. You may want to consult with an architect for exterior design. You may want to consider some color blocking too. You have good options to make this home a stunner.