The darker brick in the herringbone veers orange .. the main thing if you head towards a new roof is to get a slate style shingle, or a victorian diamond style shingle. The brick here is wonderful - definitely stay away from true grays - they reflect the sky and look blue. Blue makes anything orange look a lot more orange. You can do a cool taupe / warm gray / brown gray . . avoiding a red undertone brown is a good idea. The stone and brick on this home is wonderful . . the casements are classic, but you need some muntins. Full colonial muntins are probably too much . . something like the big cross that pella sells.

Use deep charcoal greys with lighter brick. Gutters and downspouts should be copper. Will you do another cedar shake roof? If not, consider a slate roof.

Here's a link to the muntin / window grid profiles that I cited .. consider casements with this cross muntin. http://professional.pella.com/windows/features-and-options/grilles

I agree with libradesigneye, slate look or architectural shingle in perhaps a color between grey and brown ....Weathered Wood. Here are links for products.

http://www.iko.com/products/residential/roofing-shingles/architectural/cambridge/#

http://www.iko.com/products/homeowner/residential/roofing-shingles/premium-designer/armourshake/#