here's a generalized cheet sheet for craftsman style http://www.antiquehomestyle.com/styles/craftsman.htm

for the porch, battered columns (ones that taper, but are square) are a classic craftsman look, as are clustered columns (3 or 4 on a single, large pier).

the windows would be double-hung, so that fresh air can get in, and they generally had 6 or more lights above with a single pane below.

if you've got the budget for it, you could probably ape this plan's rooflines pretty easily.
http://www.antiquehomestyle.com/plans/sears/1916sears/sears-264b206.htm

actually, this one might be easier and less $$$
http://www.antiquehomestyle.com/plans/sears/1916sears/sears-264b233.htm

A picture of the entire façade would be nice. You got sort of a saltbox and it could be made more craftsman with a full or nearly full porch across the front with masonry piers and battered columns, as mentioned above, or grouped square columns, perhaps with mortise and tendon type detailing. I would go with grouped casements upstairs, with similar proportions to the vertical windows below. Simple double-hungs, like what you have now, are fine too, and less costly.

Are you sure you need to replace the whole window, or all the windows? Selective replacement, replacement of just sashes, or if wood, addition of storm windows and caulking, glazing and weatherstripping is a lot cheaper and just as efficient. Window account for only 10% of your energy usage, so new ones aren't as big of a savings as you might think. It is better to spend your money on some spray foam for the sill and to seal the attic, and if you are ambitious, behind the window and door casing (Generally from inside is easier).

Craftman style windows are popular now, and various configurations, including 3-over-one, 6-over-one and 2-over-one and Prairie are possible. Get the kind with the simulated muntins on both sides of the glass, and preferably, in-between the glass. Don't get the kind just imbetween the glass--always looks fake and pasted on, and usually too thin. The new fiberglass windows look quite authentic, and should last longer than vinyl because of a lower expansion coefficient, closer to that of wood. A craftsman style door to match would be nice, and are easy to find these days.

I would keep and just selectively repair the cedar wood shingles, and restain. That is perfect for a Craftsman. You have virtually no roof overhang, so don't add brackets or gable ornaments. A new porch and door alone would be enough to take it Craftsman.

Thank you Yoboseiyo and victorianbungalowranch for many great ideas. We will have to replace current windows as two are from the 1950's and top large windows rotted. Thinking about double hung, 6 light on top and single on bottom and carry that style to the windows upstairs, only on a smaller scale. I like the idea about a new craftsman style door to tie it together. I'm thinking about a small porch with columns. Thinking of color combination attached. Thank you for all your ideas.

Project completed for now. More work to go in the spring.