Your house is a gorgeous, classical, balanced, symetrical style, & I'd think it will look best with colors that are in keeping with that image...even if you have to think a while to figure out what to use! The brick & wrought iron & the very size of it give it weight, so you need colors with "weight" so that they look well-matched with the rest of the house, & since the brick has depth & texture, you want simplicity. Paint the downspouts as close to the brick color as possible to camouflage them. I like the way the house looks now, as far as matching & contrast, so I'd experiment with maybe charcoal gray or British racing green (deepest green in the universe, with a little black mixed in) for the shutters, & spanking white for columns & window trim. I like the red door, but if you want a change, maybe stain the door a walnut color & use the same color on the area above the porch. That combination might give the house a "lodge" kind of atmosphere... or you could go spanking white on everything but the door & use a deep Chinese laquer red on it. Whatever you do, it's a beautiful house, & you'll have a lot of fun working on it!

Where would the U driveway be? It's hard to tell how much space there is between the street and the house, and I can't see where the current driveway is . . .

I think Hale Navy would look nice. It's a cute home. The shutters, however, need to go, or bring in some made of wood (think cedar). the wood w/the Hale color and the brick would look nice. Hale navy would look similar to this. if getting new windows, then do something like shown here^, or look at some of the pics below. Since you have the gray roof, you can do other combos too. I like the Urbane bronze on the siding, fired brick for the door, and a soft gray or white for the trim If Grover comes along, maybe she can photoshop a new color and new shutters for you here are some similar homes just to give you ideas when you're ready I love this dark gray w/the brick. but the black trim around the windows (without shutters!) and darker garage door, really make this stand out. (I could do w/o the orange door though) this is more of a teal, but gives you an idea of how it looks w/those white shutters. I don't particularly care for this tone. the white is way too stark against the siding tone w/that brick. This would look better w/painted brick, or diff trim color. diff gray tones on siding

Have you done "test spots" of the gray on the brick yet? If not, I'd start there. You may need to paint the siding a different color, depending on how the Romabio ends up looking. Looks like you have a very light and cool bluish-gray right now. If the brick ends up looking warmer, then I'd suggest a warmer contrasting color for the siding.. Also - once you do the brick, are you looking to change the door colors? Looks like you have two front doors, I'd personally change the color of the main door and paint the second door the same color as either the brick or the siding. I'm sure other folks will chime in about adding landscaping..