Lovely place!!! Not a fan of the green paint on the brick trim that you inherited nor the green corbels and fretwork either. Not sure it will be useful to go back to brick itself though since you have so much going on here. You want a dimensional shingle - with variegated color, so it has as much charm as it possibly can. . . and though I'm usually a gray fan, I think sticking with an earth tone / brown gray at the darkest is best since a lot of roof presents to the street. Unless you are brave and want to do a green or red roof - both would be charming and fitting but I think only if I could find an earthy / really mossy green would it be worth it and I've not seen anything but the sort of golf course green tone. You don't need to lock in colors like that.

Since you have wood toned carriage doors and entry, an earth toned roof fits.

May I suggest a stucco color might be best if it were a color found on real stones? I see a red brick chimney top. A mossy green, creamy white and red color scheme could be very charming with the wood and roof . . . I'd want to put the creamy white on the stucco, but a soft moss tone would work there too and allow you to just adjust the white trim to red with the green elements going creamy white . . red windows and fascia /trim would be charming here .. when you do have windows that you can paint it is a crime to do them in white! You have so much charm to play with there . .

Here are some colors to test . .
ben moore plaster of paris
bm cottage red
bm herbal escape or spanish olive
If I were doing the stucco a green, then I'd go up to spanish olive . . but keep the other tones. . . .

You'll notice the greens are very neutral, camoflauge greens . . nothing too disney . .. the white a dark white, and the red, totally charming. Don't know the colors of your neighbors . . but I'm falling in love with red painted windows and trim on a white cottage.

http://www.benjaminmoore.com/en-us/paint-color/pm15#ce_s=cottage red
http://www.benjaminmoore.com/en-us/paint-color/plasterofparis
(the lightest sort of warm white you should consider anywhere - albany white is another more yellow/ creamy but this undertone is perfect with wood doors)
http://www.benjaminmoore.com/en-us/paint-color/herbalescape
http://www.benjaminmoore.com/en-us/paint-color/spanisholive

I want that house..swoon