Painting your brick is an extremely bad idea due to your climate. Glad your photos (unintentionally) included the houses flanking you. Any future buyer will consider your painted brick home to be of less value than your neighbors' homes. The siding color "goes with" the brick...it is the glaring white of the garage door, addition siding, and downspout color that needs painting. I assume your front stairs are pressure-treated lumber, stain the wood to match the roof. IMO Landscaping will give you the biggest bang for your buck and do wonders for your home's curb appeal.

Hmmm, I really don't think the mock up by houssaon makes the house look better, so definitely don't paint the brick a light color. I don't love the brick with the roof, so what if you painted it a darker color? In this pic, the body of the house is shingles so ignore that, just the color. Definitely add some interest between the windows. Even if you don't paint the brick, paint the garage doors darker to blend better with the brick. I had garage doors that were high contrast with the body of my house. My dear friend said it was like two beady eyes staring out. I painted them the same color as the house, dressed them up with some hardware and it definitely looks better. Ideally you could replace them with wood look doors but I think your money is better spent elsewhere if you paint them. What zone are you in? That would allow better advice on plantings. I feel you need something large and evergreen to keep the interest in winter.

Roof: I would stick with the GRAY roof rather than changing to brown. Gray is much more versatile. Brick: I like your brick as is. Don't paint it. Front Door: Don't replace with a 'Craftsman' door. Your house isn't Craftsman. You can get an appropriate wood door that isn't Craftsman. Garage door: Paint to blend with the brick color or one shade darker than the brick. Best to not accent the garage door. You can remove the plastic inserts in the top garage panel so that the windows are square rather than that sunburst pattern and that will be a very nice update for your home. Shutters: Remove them. Your beautiful windows aren't designed for shutters and they clash with your exterior. Porch posts: Don't accent your posts - they aren't a feature. Have the color blend into the house so use the brick color. You have a great home! It just has a mashup of a couple of different styles now. When you finish your improvements, I would love to see how it turns out. Have fun!

landscaping will play a big role in your curb appeal. I'd also square off the garage door. let me show a bunch of pics of similar homes and you can decide what you like. almost identical to your model. Notice the transom window over the new front door, the shake siding. (you'd have to paint your brick. Romabio!) the arbor over the garage door, but more importantly, look at the beautiful landscaping. same w/these most of them have the elevated front porch like yours. ok, now the house I love this dark moody siding and garage door color. You need a garage door jus like this. with the white trim, it would match your white windows. grayish green color. shake and siding. transom window again. this was one that Bargain Mansions did. it looked like yours. she replaced the upper siding w/the vertical board and batten, and painted the brick white. added the black windows. new lighting, and new front yard. it was rather inexpensive but had a big impact want to go MCM? love this one you could totally do your house like this one. they painted the brick, siding, new larger upper window and new doors. and lighting and landscaping. lastly, if you keep your brick and just picked a new siding color. and new doors. kind of blah, but it looks better than what it did.