The brick color is moss town with light buff mortar. Windows are pebble grey from Marvin Windows Infinity collection.

It's a corner house and technically the doors are on the side of house along with garage door... The first pic shows the one we need to paint under porch. Second shows the "side door" which is the one we go in and out of all the time. The last pic shows the "front" of house.

Your home is very nice but the problem you're having deciding what route to go is that your home is a mishmash of different styles. The roof screams coastal south yet the brick yells colonial. Add the shutters (colonial) and the Roman pillars (colonial) and it amounts to a split personality. The first thing I would suggest is getting rid of the fake shutters. Unless shutters actually have a purpose it's better to ditch them. The columns are a little more problematic because to change them will incur significant costs. I would go with a simple square column for their chameleon-like properties. But make sure the dimensions work in relations to the size of the home. As much as I am an avid gardener I agree that the shrubbery at the house perimeter needs to go. It overwhelms the home and makes it appear much more squat than it actually is. I don't have a problem with the other greenery, though. I have no experience painting brick in such an environment. Bricks helps release humidity in a building. In Canada where I live, painting brick can be problematic. The continual effect of moisture trapped in the brick can deteriorate it over time. While I live in the north I have a place in south Florida. Most painted homes I see are stucco which lends itself to paint. Paint would be an easy and cheaper fix in the short term, but I believe it would require constant attention and over time the costs could multiply. I think your dissatisfaction in your home's appearance is less because of the brickwork but because of the stark contrast of a very light roof against dark facade. Try painting your front door a different color (the red just accentuates the colonial vibe) that works with the brick and the roof before making the leap to painting the whole house. I suggest SW's Sea Serpent. Paint the columns (not the door color) as well but a muted shade like SW's White Flour to get an idea of what your home could look like without going all in on the facade. I noticed you used an app for a combo of house paint and shutter colors complimented with blue and white greenery. As an expert gardener, I have to say my experience with blue and white florals paired with rich dark greenery , which are absolutely sensational, really only work in environments that enjoy a lot of shade. It's the shade aspect of the colorations that makes the pairings so luminous. In a sun drenched environment like south Florida they look washed out. My final suggestion if cost is not an issue would be to hire someone, after investigating the effect of paint on brick, to stucco your home's exterior. No better time after pulling out the foundation plantings.

Thank you all for the input! @hallettco, I appreciate the run down on what is involved with the trim, I had no idea it was that much work. Since we are at the end of the renovation that started in October, and they've already finished repairing the siding on the back, I don't think it is wise for us to start cutting up the siding! At least I know now to rule that out. It sounds like re: shutters that we should remove them from the horizontal windows and bay window (assuming that the brick looks ok underneath, we shall see). @Patricia Colwell and @houssaon, I'm curious what you mean about the size of the shutters? They are taller than the glass part of the windows, so I'm not sure how much bigger they could get?