To make it look more craftsman you will want horizontal instead of vertical siding and contrasting painted trim. Search the houzz photos by "Craftsman style exterior".

I personally think your house is really awesome and in the Portland area those homes are becoming more and more sought after, as they have become older people are buying them up and remodeling them in a way as to keep the NW contemporary architecture alive and well

Hi, I found your post because I have a very similar design dilemma (contemporary house in the northeast). I have a couple thoughts for you:

1) The siding is all very uniform. Change it up in some areas (focus zones) to add dimension. Like your idea for some shingles. Stone would also look great on a wooded house. (Keep with the warm tones of the house)

2) Entryway -- I wonder if you could change up that angled roofline a bit, make the entry more prominent, and add some craftsman columns. Also, I'd find a way to get rid of the deck rails near the entry. They look kind of dated and uninvited. Maybe add a little stone wall instead.

3) Whenever the time comes to re-do the roof, metal would look gorgeous. (There's a home near me that has a metal roof -- with long planks, like the ones you see in Vermont a lot -- and it's just stunning looking)

4) Quite honestly, I don't think you can really do much to change the overall style of your house without spending an inordinate amount of money to change rooflines, etc. So find ways to embrace the style you have. I think your house is really pretty!

ps. would be so grateful if you could give me some ideas for my contemporary house too! https://www.houzz.com/discussions/advice-80s-contemporary-exterior-makeover-dsvw-vd~3847227