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.

Help! I would like to update the exterior. Should I go lighter with the base color and the trim? Should I paint the brick? Thank you.

Here is a greenish gray with white trim. Your tall arborvitae need to be removed from in front of your windows, which I guessed at the shape in this image. Your home could benefit from some colorful landscaping in the front.

Kiimela, it just depends on how white you want the white. Alabaster and greek villa are warmer whites that lean a little yellow. make sure to get some samples and bring them home. I did these three on my home, with the Swiss Coffee (Behr) on my stucco. See how dull the swiss coffee looks against a bright white? But,,, this is how bright the white turned out on the stucco! Also have a rental house w/Swiss Coffee and black trim. (Behr colors) It's a nice combo. consider getting a new front door though. if you must keep yours, paint the entire door and side lites black or red. I'd prob just go w/Pure White if you're picking SW colors, for your place. Paired here w/Hale Navy, both of those would look nice. Or do the charcoal. just do a dark color for the trim against the white