what's inside the dormer ? Is a window addition warranted ?

I would add a window to the dormer even if this is attic space and I'd stick to the clapboards (perhaps combined with shakes) and the brick. A brown or slate grey roof would look good, which would allow you to chose different siding colors from what you have now. I like a medium blue for the siding and a red door. I'd beef up the columns too.

Your landscaping need some work. The shrub on the far left is way too big. Hopefully you can prune it back and add vertical shrub on the other side of the window. I think your entryway would look better without the row of evergreen bushes hiding it. It looks like you have a big front yard so you might want to develope a planting bed with two or three ornamental trees, shrubs and flowers, which you can enjoy from the street as well as the house.

Notice this blue house: The deep dark blue grey siding would look wonderful on your house combined with the brick. I would even go for white shutters. There are some interesting plants in the photo, too. Like the PJ hydrangea (back in the corner by the house), the Japanese Maple and the small mounded bushes.

Thanks fer your remarks so far! My "dormer" is in an upstairs entertainment room, and that particular wall (which is the dormer) gives the long and skinny room more headspace. My wish would be to extend the "dormer" to the front my home, Which is above the 2 car garage. But currently that space houses the upstairs furnace and air conditioner,duct work, not a simple addition! Isint it always something? Im not a big fan of Colonial/ Williamsburgh blue since i grew up in the 80's and the was 1 of the popular colors at that time. LOL.

Come to think of it, why I never thought about putting in a window up there? I dont know, lol. I guess to me, it just looked like there wasnt enough room to get a decent size window up there. Thanks for the provoking thoughts, my husband might think otherwise!...lol

I would not add stone to the facade if you are keeping the brick.
Pulling the upper floor gable dormer out over the garage is a simple and cheap way
to add both square footage and charm to this unusal facade. Moving the HVAC or allow a new "room" for it in the addition is not very difficult to do.
I would also ask why you want to replace the current asphalt roofing shingles. They look like the more expensive 3-tab shingles, which mean they have a long life expectancy.

If you would like to see some ideas on stone and brick combinations, here's a good site to help.

http://www.flickr.com/photos/buechelstone/sets/72157626640764781/

I love the darker blue gray suggested above. Plus, a window would look great- with white shutters. Ever thought of painting the brick?