I want to change the look of this house to be more modern if possible by changing the bow windows to 1 large flat window. Do you think it will out of place? I'm also planing to change the entire front steps and pathway to concrete.

If you want a larger window, shouldn't you do that before the siding goes up? Not after?

If you change out the window to something more modern the trim around your door should change to something more modern, new door and the windows will need some thing to make them more modern looking . This pic might give some inspiration, just be aware when you start this you will have to follow through with the upstairs windows as well.

I agree stop siding until you make decision about window, door etc.

I already change all the windows on the 2nd floor.

Hi.....I would suggest you box the bow to the existing railing, removing the railing, and add
tall windows similar to the width of what you have but more dramatic. I would cover that with some type of wood vertically. Use the wood as a trim around the door, remove the stairs metal railing and use a cable system with wood. The wood will be a nice contrast to the gray, and the tall windows and vertical wood will correct the flatness of the home.

Examples of decks using cable railing as guard rail.
http://www.houzz.com/projects/364179/Deck-Cable-Railing

I put window boxes on a second story window once. Used fake greenery. Looked nice BUT came home to teeny tiny mites in the bathroom that had found a way in. I think I bird nested in the box and perhaps one of her babies died or the mites just went for whatever was left. So don't do what I did.

Matilda-thank you for the suggestion but could you show me some examples of a boxed window.

Hi.....I'll see what I can find, I realize a picture helps.......

Hi.......Definitely had a problem trying to find what I was talking about, and I apologize for the blurry pictures, taken off my computer. I think you will understand the bump-out (box) and also the windows. There should be a break going across from the bump passed the door,
to separate the wood from the charcoal above, the trellis idea is one option.

Hi...Sorry, one more......

Thank you for the ideas Matilda.

It's really too wide for one piece of glass, and I think it would give the home a storefront appearance. I would stay with the current style windows because they match what you've already put in. Just install them flat and maybe have the end ones crank out for ventilation. I'd also go with simpler molding on the front door and change the door to a more modern style with a pop color. Consider painting the lower siding a lighter mid tone gray.

So what did you end up doing?