I think you can get the craftsman look with paintcolors. Idea 1: Lift the entire roof. Idea 2: A cross gable (hope this is what it's called, had to google it) with the point in the middle of the garage door. Of course get it drawn by a pro and see if you need any permits.

To transform the post-modern home you have to a more traditional Craftsman design will take an architect's understanding, creativity and vision...and a builder's knowledge of costs and technique. Look for local help here on Houzz. Hit the "find local pros" tab on the header above and follow the prompts.

Thanks @Demesne Design - I flipped through some images of the Prarie style this morning and agree that this style is much more in line with the house. We are just not used to seeing the Prarie style in our neighborhood! Do you think a bonus room on top of the garage would mess up the lines/aesthetic?

Thanks @Ironwood Builders - I do expect we will need to engage an architect and builder on this, but looking for some ideas as we start this process. This has been helpful so far!

Dave M, I do think that raising the roof line on the garage will make some of the transformation easier....architecturally. There are a number of considerations to take into account when adding living space as a second floor. Starting at the ground..is the garage foundation large enough to carry the additional loads?...now walls...and garage door headers...same thing! To get the bonus room you may end up demolishing and rebuilding that entire garage. My reaction is to try to hold up that expense and reserve capital for the entire project. Sort of why I suggested an architect in the first place....then you get big ideas and big picture creativity...but you also want someone like me along for the ride...to wrestle with the budget for those big ideas.

@Dave M, It is very possible to maintain the aesthetics with an addition over the garage. As @Ironwood Builders said, it takes a design professional with understanding, creativity and vision to combine the existing with the new in a way that brings it all together. You are doing things the right way by exploring possibilities, being open to suggestions, and deciding what you like.