Why does the roof line sag so much? Unless its by design, Id try to get that straightened out.

Its too bad it lost all its 1950s attributes - why it looks "hideous" (your word) is that you now have all these random elements - two types of windows, doors, various types of siding - none of which really relate well to the others.

The frequent advice you get here in the old house forum to stick with its original design and intent is because thats generally how it looks best and retains its character. You might try home dec forum - they do exteriors over there as well as interiors.

@currentresident

When I came in, they already removed the rotting left side of the house which was the only part of the home that wasn't brick and everything else. The house was built in such an unusual way. This is how it looked before it's been messed with.

@bibliophibian

Thanks for the suggestions! Here was a sketch of a color concept that I had in mind for the house. I'm not to sure about it though.

I think the black on white is too stark and emphasizes the odd lines of the house. Try to soften with grey on grey then give the eye something else to focus on such as landscape, maybe a bench or rocker on porch with eye catching container plant. Paint door to match porch accessories. Paint roof peak thing to match roof.

Aha I see where you're coming from - you are making it better, keep that in mind! Very sorry if I sounded preachy, its because so often people take away the cool old features, then wonder why its lost its charm

I like your sketch - not the black and white necessarily, but it shows how unified color CAN pull it together. The other thing is the door. Youve got the right idea in the sketch with the single horizontal window -

Or maybe think about one of these - http://retrorenovation.com/2014/07/22/4-places-buy-midcentury-entry-doors-home/ 

I like the ones w 3 horizontal windows (like in top row or under #8) and also the ones with 3 diamond shaped windows - those are simple, but would add a lot of style.

You might be able to find something similar in your local Restore or architectural salvage.

Dont do a door that might look
cottagey or craftsman ... or anything from this century from off the shelf from a
big box store.... or it will just add more visual chaos, not unify.

The door is your one chance to make an architectural statement that gives it a touch of class and charm. Just keep it simple. As others have said, keep the paint colors simple - youve already got enough going on.

Can the windows be painted? What color is roof?

Builders Choice exterior doors from Home Depot - something like this! http://www.homedepot.com/p/Builder-s-Choice-36-in-x-80-in-Earthen-3-Lite-Rain-Glass-Painted-Fiberglass-Prehung-Front-Door-with-Brickmould-HDX163054/204855490

Thank you for the suggestions! The roof is currently flat and I haven't been up there to see what color it is, but the sloping side is going to be fixed. The windows can be painted, but the lines on the inside of the windows can't be. What color do you suggest the exterior and trim be?

Are the pane dividers in the windows black? If they are and it's not something you can change I would probably do the house light gray, the trim dark gray and the door something bright like red or turquoise to pull the eye away from the peak. Those midcentury ranches actually look really good with monochromatic color schemes because they're so linear.

I would add some window shutters on the outer windows.

No, no shutters. Just my opinion.