You could put a plant in that spot.

Or continue the molding/boxes into the LR area just to finish that wall. It’s hard to tell from the angle of the photos if it is best to separate the LR from DR and if that is the spot. Hard to tell from the photo the relation to the column too.

Add a vertical piece of molding to stop the wainscoting and paint away.

I would remove the chair rail you have there, because, it just doesnt look right ending like that anyway. Its a very pretty room, but, the chair rail seems like it doesnt belong.

I think Rachel Lee has the right solution. Have a carpenter come in and add some decorative molding. You’ll need it vertically, where the chair rail ends, and perhaps some additional moldings around the squares. It looks like someone was trying to create the impression of wainscoting, they just didn’t quite finish the job. You’re more than half way there.

Least trouble and cost is not doing a white half wall and painting everything the same color, to provide a less broken up visual and also allowing both sides of rooms to work together.

You can continue the molding/chair rail to window and match the other side if possible, but suggest you test paint one lower wall white and other wall all the same color including moldIng to see which you like better.

I agree with putting a piece of molding at the end of the chair rail where it enters the living area.
All this talk about "cohesive" less broken up space ignors the fact that the dseign of the rooms, the columns and chair rail are designed to define the eating space.

Lovely room! I like the idea of the white below the chair rail.

Thanks for the ideas, everyone! For those of you who were asking about the relationship of the columns to the chair rail, the columns are placed around where the chair rail ends. Here are some more photos. As you can see, one continuing wall is much longer than the other. And the previous owner (or, more likely, stager) put a plant near one of the columns, probably to cover the abrupt end of the chair rail!

For those who advocated painting all the walls one color, would you go with semigloss, or a different paint finish? I was planning to paint the under chair rail area semigloss white. If I did paint all the walls one color, it would be white.

I'd paint the wood trim in a semigloss or satin finish and the drywall in a matte finish. Painting under the chair rail a different finish will bring up the same problem of where to end the semi-gloss.

Would you use different whites for the molding vs. drywall? In my past experience, the same color looks a lot whiter in semigloss, so it makes the drywall look dirty in contrast if it's done in the same color.

I've never found that to be the case, but if it bothers you, then select a different color for the drywall.

I'd get a pro in to build a stopping point for the mid-air trim. Then I'd paint these colors; believed to be Navajo White walls and White Dove trim.

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Ooh, those colors look pretty! I wish I could find some pics online of chair rails stopping mid-wall, ending with vertical molding so I can imagine how it would look.

The rest of the house will probably be Balboa Mist with Oxford White trim, if that affects anyone's color recommendations.

would you do thick trim or thin trim for the vertical piece?

painter put in vertical trim, but does it look off? I was imagining that it would start below the chair rail. should i ask him to move it to below chair rail? and are there supposed to be nails in the trim?

The nail holes need to be filled and painted.

other than that? do you think trim should have started below chair rail?

IMHO, this does not look good at all. I would not except this solution. It looks like you just slapped up a piece of molding. It needs to be integrated more with the existing chair rail and base molding. If you move it over to start under the chair rail, it would be too close to the boxed out trim. If you want it to look like it is meant to be this way, he really needs to move the trim under the chair rail and shorten the width of the box so the spacing is the same as the distance between other boxes. Also, the trim piece should not stand proud of the base piece. You need someone that knows how to rework this to look professional.

Can you post photo from further back. Can’t tell much from this photo.

I wouldn’t mess with the moldings. This would create pretty look and distract eye from moldings. You will not get that molding right unless you take it all down and redo it. Big project.

Thanks for all your advice! Now I need to find some good fake plants (no green thumb) to go there! A more permanent solution will have to wait because this painter doesn't really do carpentry....

I haven't bought any silk plants in a while, but have had great luck with ones purchased from petals

https://www.petals.com/artificial-and-silk-plants

The trick with faux plants is to get proper style for space. For this location, I selected Upright Traveler Palm. Also, place in nice looking pot not ones that plants sometimes come in from big box stores. Find fern stands to place them on because you get height without too much width. Select plants with wire in leaves so you can bend as needed.