Whatever you choose to do, those red gables got to go!! It’s clearly a great house, but looks pretty loud and disjointed right now. I think you need to tone things down from the brightness of that roof. If it were me I’d maybe do a cream color for the eaves and outer trim around the windows, and maybe a burgundy on your window sashes (the interior portion of your window trim right next to the window panes). The gables should be something that tones down the metal roof too, maybe a sage green? I don’t hate the current trim color around your windows (looks like camo green in picture), but you needed to keep going with doing something else on those gables!

Its an adorable house, just a bit drab. I would paint the trim all white, and those red gables too. Those red gables were never a good idea. Some nicer landscaping would do a whole lot for curb appeal.

I would use 3 shades of green. Facia being lightest, gable medium and window darkest.

I made a photo of some of the ideas (Thank you by the way!) and the best result i got was this what do you guys think, i’m not sure something still seems a little off to me!?

The flowers are a big improvement. I dont like the gable color, it doesnt seem to go well with the brick. Pick a light color from the brick, if you want them a color. I also dont like the red on the windows. I would do them, just plain white. If you really want a red color on the windows, then it should be a more rusty color red that goes well with the brick.

I would stick with a soft sage green for an accent color. You don’t need another shade of red. New foundation plantings will help too.

What a charming house. I think you are on the right track with the green, but maybe just a shade or two lighter.

Whatever this shrub is, it needs to be gone. What a difference it would make - looks like there’s a beautiful porch there, but it’s hidden.

I think your rendering is moving in the right direction, but I agree it’s not quite there yet. I would avoid the use of white— historically, craftsman style (which your home is a really great example of!) is all about the use of earthtones, and I think white would feel too stark against the backdrop of your brick. I do think the use of greens, creams, and maybe even a pale yellow could work well if you find the right combination. And I do kind of like the burgundy sashes as this draws out that craftsman style, is a common style element in craftsmans, and might help to ground the roof a little. But I would still play around with a variety of different earth tones to find 3 tones that work well together, draw out those great architectural details, and complement the brick and roof.

And I agree with others about the bush— I think you could start with a very heavy pruning to see if it will work at half its current height and width. Excited to see what you land on and hopefully some more regulars join in to give additional color scheme ideas!

Go over to landscaping/gardening forum re: bush and planning landscaping that frames the house and adds to its appeal. That actually is quite a lovely flowering shrub, is it a rose, or ....? No cuts unless you have a plan - how you prune and how much depends on what it is. Some species actually improve with drastic rejuvenation pruning and others will be thrown into shock they don't recover from. Also note there are ways of pruning of roots and branches in stages over a year or two in preparation to eventually transplanting it - IMHO worth doing esp if this is some sort of heirloom .

IMHO there is no right and wrong about this - some of us like lush cozy cottagey plantings while other folks don't. I dunno, Id have to see house more from left and front angles to judge.

Agree with above, colors should be earthy tones that work well with your natural materials and red metal. This could include a version of white that has a teench of brown creaminess to it. I would limit to 3 colors, maybe 4 if front door is to be emphasized. This isnt a opulent "painted lady" type of house. The 60-30-10 guideline works with exteriors as well as interiors. Obviously red is your main color (60%) , with the gray-green at 30% and cream white at 10%.

Those colors so very classic early 1900s - love it! Have you tried to see what were the original paint colors? Not that you have to turn it back to that, Im just curious! Tis house has a lot of nice details incl. the brickwork around the base of the house.

As mentioned above the first thing that needs to go is the giant tumbleweed. Gables the trim color would be a starting place. Trim all the same color. Are the windows wood? If so paint them white with the trim and gables to match.