I would select a gray/green tone. The low roof is over whelming so not too dark as it will make the house look smaller than it really is.

whatever you choose, paint all the trims and the siding the same color, you have enough interest with the brick, no need to add a lot of contrast trimming out every window and door.

... add bright purples and pinks for the chairs too.

I think your current white is too bright. With the brick, you want something softer, like a warm cream. I think the brown trim is too much of a contrast with the white, particularly on the end of the garage. I'd got with cream or a warm sage green, but slate blues will work, too.

I would strongly recommend getting rid of some of the asphalt. If you need occasional parking for large numbers of cars, use blocks that grass can grow through. It really softens the look. Alternatively, you could put an island in the middle of your sea of asphalt with a tree or some shrubs. Just break it up. It looks like a mall parking lot.

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Thanks for all the input! Sounds like warm green or gray is the way to go. I'm attaching a photo with some sample chips I had for reference. I happened to have Escape Gray, it is in the middle. Our garage door is white but the current siding color is close to SW Silver Gray (at least out of the handful of swatches I had, that color was the closest). These were taken at the end of the day, so not great light. The front of the house faces east. I'm also attaching a close up of the brick and the soffits. I would love to go taupe and add some fun accent colors but my husband isn't a fan. We both like green, blue and neutrals. Would any of the colors here work? Everything seems to have a blue tint in this photo but it is just the lighting. I'm going to get more chips tomorrow.

Thank you for the helpful idea and photo with the parking blocks. I will look into that!

I should have mentioned we will be replacing the front door and garage door soon also.

The problem is your roof. The color does not do anything to enhance the color of the brick. If you changed that out to a warm-toned mid to dark brown, it will make a world of difference -- then paint choice will then come easy. If changing the roof isn't in the cards in the not too distant future, I'd change out the garage door white to a creamier color that coordinates with the siding and leave the rest be for now.

Looks like the driveway should be more than a huge expanse of black nothingness.

There are lots of alternate solutions for driveways.

It wants to be a green - grey. One color on the siding and two shades darker on the trim and garage door.

I love the way you asked the question! That is the right way to think about it. I agree with Kendrah, green-gray. Make sure you don't lean blue at all because that will bring out the orange tones in the brick.

I chose a gray from your roof for the siding and garage door or wood garage door. Simple with just two colors, monochrome look with the roof and siding so they blend.

Dark trim as the current downspouts and your windows, they are already dark and a nice contrast.

Replace the shrubs and a wider planting strip. A more substantial porch post so clad it.

The house appears less squat and the eye is brought down from the roof.

I don't have software but here is a rough sketch to show concept. This is not a paint color, just a guess.

The wood garage door.

Darker siding with lighter wood.

You want a darker color that coordinates with the brick so it "hides" the brick. Siding (Olive-Brown tone) Benjamin Moore "Dakota Shadow" (447) . Garage Door , Benjamin Moore "Branchport Brown" (HC-72)

I am fan of soft greens (I repainted our Brown house Sage.) But George has the best choice with that olive brown that blends with the darker shades in the brick. It unfies the house and thereby makes it look taller. It becomes a great neutral back drop for the green in the planting. It is warm and inviting. I think this is what the house wants to be.

Because the brick cuts the house visually and the roof is dark, it feels squat. I’d look to create a more seamless transition. You could lean into a MCM feel and be sure to enhance the entrance to help bring the focus away the driveway. See how the roof and siding being the same shade makes the house feel higher and how the brick becomes an important feature by the accent color (garage door and posts).

I’d change the posts so they match and if needed, consider a new door.

Wow, I came to the right place! You all clearly have skills that I do not. Thank you for your help and advice, especially George and Tracefloyd for doing those renderings (or whatever they are called). This has been so helpful. I tried every gray-green SW had to offer (and really loved some of them) but none of them looked quite right with the brick. George, olive makes complete sense. I have olive green velvet pillows on the couch that I leave out year round because they go so well with the same brick fireplace. I've got several sample olive colors including the ones you mentioned from BM. I just need to check them during different times of day and cloudy weather (we don't get a ton of sun here so I don't want to pick something too dark). Tracefloyd and Maureen you helped me see that darker is better than lighter. I was afraid the dark would make the house disappear with the dark driveway and large roof, but it doesn't.

We did have the roof replaced very recently. I tried to pick a shingle color that would go with anything but it reads much cooler in the sun than I had hoped. So all the white patches on the fascia are just repairs that haven't been painted yet. The back side of the house is just siding and a painted deck. No brick or window trim. I think a dark color will be great, I just don't want to go too dark so it doesn't look spooky during the darker months. I think they call it moody. :)

The roof drives the color because it is so dominant. George and Maureeen show a house with a very dark roof but your roof is light so do not go too dark with the paint color. Dakota Shadow and Branchport Brown colors are not what show in his rendering.

Keep in mind green will make the brick appear more orange because of the contrast. It might work because you want to draw the eye to the house, away from the roof. Why I suggested exposing the brick by removing the big shrubs.

Try Benjamin Moore online Personal Color Viewer visualizer. Upload a photo of your house and "paint" it using their colors. Sherwin Williams is ColorSnap. Create your own renderings!

Here is Pinelands and Bear Creek which are further up the paint strip from Dakota Shadow and Branchport Brown.

To me the orange and green colors makes the roof appear blah. Bear Creek garage is very nice with the roof because of the gray in it.

Here is the brown in George's rendering.

This is a little lighter wall color using your other image that shows a light roof. I still think it works. And yes the pole would look better thicker. Buy a pole wrap kit at Lowes online.

The problem is your roof. The color does not do anything to enhance the color of the brick. If you changed that out to a warm-toned mid to dark brown, it will make a world of difference -- then paint choice will then come easy. If changing the roof isn't in the cards in the not too distant future, I'd change out the garage door white to a creamier color that coordinates with the siding and leave the rest be for now.