I like trim that matches the window trim, have you thought of white trim? Also I don't see coral as complementary to the brick

You say you want your house to look like it did in 1959, why? Your house has oodles of potential to look like a cool midmod house and that's not quite the same thing. Your railing looks like it could be from 1959 but not worth saving in my opinion. I like the dark grey or black that is already on the house. It goes really well with your brick colour. I would take that same colour and paint out all the white trim to that same black. Your stairs is where I'd put the majority of your budget. I would redesign the stairs so that you had a big landing on the ground level in front of your house. So you'd take maybe 5 steps up from the driveway, then have a large landing that was the same level as your front yard grass. Then another large landing half way up to the front door. Your stairs would take up a much larger part of your front but would be a nice leisurely walk up to the front door. Right now your stairs look like quite a hike.

Also, coral for your front door, not a good idea. Stay away from anything in the red family. Go with blue or teal or black.

With that color brick I would do white trim everywhere, especially since you have the white vinyl windows already. I second the blue idea for the door.

Thank you to all of you for your thoughtful input! We have a separate project for the stairs and that is exactly what we are planning @Brown Dog

To clarify, we are looking at restoration, not renovation, and the vinyl siding by the windows would not have been done at all. We plan to redo the siding and want it to be more complementary to the style of the house.

Unfortunately, with vinyl windows it is not recommended that we paint those. That will have to stay creamy in color. Thinking about how we would redo the siding, what color would you take up through the windows? There is vinyl trim that will be taken off, but the window casing will still be creamy. What color would you paint the soffit and fascia?

You have vinyl windows everywhere which aren’t changing which is fine but that locks in your colors. Some version of white. The large windows appear to be ivory- the small slider in the foreground appears to be bright white. If only the large window is ivory I would paint just that window white and have bright white trim everywhere (they make paint for vinyl). If all the vinyl windows are ivory I would use a white like Benjamin Moore linen white which is a softer white so the ivory vinyl will blend in.

Thank you @HALLETT & Co. The windows are all the same color vinyl so I think we could avoid painting. When we redo the siding, would you paint that white, too?

Yes. You have three elements on that home- trim, body, and accent. Your accent is the front door, I would use turquoise. The body is brick (yay). The trim is all the wood/ vinyl elements that are currently a mix of ivory, white, and dark brown. Paint it all one color so they read as one element.

Have you pulled off any of the vinyl siding yet? On my house we had a bay that was vinyl and the siding under it was in nearly perfect condition (except for a Lot of paint)

Unfortunately we did pull off the siding and they added some insulation and took off the original siding. We were hoping that wasn't the case. :-(

I appreciate your help @HALLETT & Co.!

Could you take a picture of the house straight on?

Right now I am thinking of white for everything except the fascia. The fascia (and gutters) could be the color they are now.

Here is another angle. We have about 4 different colors going on - light gray (vinyl and garage door), cream (vinyl casing for windows), and dark gray on the fascia and eaves. We'd like it to be more uniform and will redo the siding on the front of the house by the windows.

Again, we will be redoing the entrance to the house, but that's for the second phase of the project.

Geez I would do everything including the windows in dark gray

That is what we were originally thinking - thank you for the mock up @BeverlyFLADeziner! Will it be a problem to paint the window trim since they're vinyl? I know that Sherwin Williams and Ben Moore make paint for vinyl, but none of them are this dark.

I can't seem to get my photos to upload. I will try to post again.

Love your house! Not much to do. I would paint the lower section the same dark color as the top.

I thing the retaining wall needs attention. The stack stone is not right.

Is is possible to replace one of the doors with glass? Many MCM have a glass panel side light.

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Thank you @houssaon. We do love this house and have worked on restoring/renovating the interior and now we're moving to the exterior. The landscaping and new front entry steps are the next big project to begin this summer and we're very excited to have it feel more cohesive and appropriate for the house and lot. We have thought about adding a sidelight, but the front door is actually original to the house and has such amazing detailing. It's in great shape and we're hoping to keep it if we can. We'll paint it and see if we want a door with a sidelight - I love the one you posted. Thank you!

I agree you should keep the original door. It looks like the one with the wreath is the functional one. I was thinking of replacing the other with glass. But it will have a big impact once it is painted.