With your grayish roof a medium light gray field, white trim. No shutters, enlarge the trim around the windows instead.
Cut down the bushes in the front of the house as they are over grown
and hiding that beauty! Pick a nice color you love for the doors navy or red would look great. Beef up the post holding up the roof over the side door.

If you don't want to soften it up because you want to house that everybody drives by turns to look at, a nice deep blue with crisp white trim looks amazing. And it would work really well with the structure of your house.

the second pic here shows a softer blue

Lovely home on the hill.

Those curved concrete stairs add such a nice touch to the entrance. I would make sure I border them with light colored hostas to add an accent in the shade and make sure that when the house was washed before being painted those stairs would get washed and bleached too. They will look brand new.

Adding shutters and accenting the trim on the house would add more texture and interest to the home overall.

This gray home with the dark gray shutters and black window trim makes a very handsome statement IMO.

The combination of white with white, especially with board and batten shutters can make the home take on a farmhouse casual appearance.

I especially like this gray siding with white trim and shutters combination.

This combination from your ideabook is classic and would stand out on the hill:

Classical Architecture · More Info