What drove your choice of gray?

I would probably paint something like October Mist or Misted Green (Benjamin Moore). that would complement the pine.

I would do something as simple as possible with the windows - maybe an up/down shade. But I am not sure how that works with non-rectangular windows.

Winterwood is more gray, but still has some green.

Sweet house! Love your wood.

Aside from turning the octagon windows into the death star:

or completely highlighting them with weird built up ornate trim:

probably the best bet is to build a frame to put shutters over them:

Some great colors for walls near yellow wood:

Benjamin Moore:

Gray Cashmere:

Sherwin Williams:

Consider upgrading the light fixture to complement the new barn door hardware:

Also consider having the dresser and the armoire swap places...the tall cabinet looks a little squished between the windows and under the ceiling.

Wow! This is all incredibly amazing advice and suggestions. thank you everyone, I would never have thought of all of this myself. Now I have some hope!

I like Gray Cashmere (one shade lighter than Misted Green) with a white trim, but with your pine I prefer a midtone color, Too light will be washed out looking next to the rich color in the pine.

Most designers will agree that you should get the bedspread first and design the room around the bedspread. I do things a bit differently, selecting base colors for my whole home and decorating around the color selection. My reasoning is that I own 5 bedspreads and keep each for a few years before wanting another change (One for each season and one for Christmas). I am always on the lookout for bedding that works with my colors.

If you get expensive bedding and keep the same thing for a long time their advice is sound.

I really like gray with wood. How about Revere Pewter by Benjamin Moore or Storm, two of my favorites.

I really like the squared shutters for the windows.

The squared shutter idea is great, although I may need to save up a bit and have an interim plan. The paint color suggestions are super, some may even match my current bedding. Does everyone agree that I paint the entire wall above and below the chair-rail the same color?

Rawketgrl , where did you find the top barn-door like ceiling light?

Are the windows centered on that wall?

Here you go:

https://www.lampsplus.com/products/castille-22-inch-wide-bronze-pendant-light__1g894.html

pennydesign - Not really. It was almost as if this room was at one time two rooms made into one. The two windows around the bed ( 3rd photo) sit on top of the chair rail and look symmetrical to the bed. in fact I even thought about moving the tall armoire in from of the octagon window on the far right to basically hide it. The downside is there is a lot of light coming from that window.

Yes to painting above and below the chair rail the same color. Post updates when you can, your space is lovely.

I will post updates and thank you all. I purchased 3 of the paint samples suggested today.

Well, I feel as if you could make the windows a part of the bed in a way...not literally, but part of the whole wall design. Both your bed and the windows have similar angles. Your pictures muddle that up a bit for me...I'm still thinking on it, but in the meantime, I would get rid of the chair rail so you have a less choppy look...

pennydesign- The issue with removing the chair rail is that the wall above is textured and the surface below is smooth. There was pink flowered wallpaper previously on the lower section. I will not be able to have the entire room re-texured smooth (of course it would be ideal) so I think i need to keep the chair rail. Agree the pictures will be removed. Thank you. Keep thinking about the windows and bed....

Okay, keeping the rail...

I'm thinking that drapes behind the bed and extending past the windows is your answer here. You can have sheers right where the windows actually are...a bit like this, but with a skinny sheer bit so that it disguises the shape and size of the window (makes it look like a "normal" window), plus the drapes will also help the rail disappear a bit. You won't be going to the ends of the wall, just a bit on the other side of the windows...

I don't see nightstands, do you have any?

Can the armoire go on the other side of the room (not where the barn doors are, but the other end....I don't think you show a picture there)? If it can, I would have the area near the small window/doors as a little seating area...a comfy chair and small table...that will visually separate that window and area from the sleeping area so that the window there looks like part of that vignette...

I won't write a book here if you're not interested, but if you're considering it, let us know...we can help with drape fabric (as it shouldn't look overly lush) and nightstands...also, don't paint until you have your bedding/drapes...

I agree with the suggestions to consider a greyed soft green. I think a standard grey in no way would go well with the wood. I think sometimes people think that to update a room, grey must be used because of its currently massive use without considering the rest of the room's features.

pennydesign- the armoire only has two spots - next to the barn doors or its current spot. The other wall not pictured is a closet with mirrored closet doors taking up the entire wall. The current nightstands are one bachelors chest with black marble top (which will help with the black accents) it matches the bed and the armoire, the other nightstand was a round table. I need to go out of town for a few days, when i return i will try the paint samples and take photos of the 'nightstands'. Once i get the room painted, I will re- evaluate the drapes. My first reaction is covering the entire are behind the bed is simply too much fabric and over powering. I truly appreciate the ideas and the photos. Thank you.

Hi...I don't favor the chest next to the look of barn doors, but armoire's simpler front, yeh?

Large surfaces of ceiling, headboard, and armoire - will those 'permanent' stains and such be altered?

Room to me doesn't need much color or pattern, cause of interesting items already there. This could soften ceiling, etc....in the right fabric...

Hunting Lodge - Oxford, Maryland · More Info

Seems good to match fabric of 'headboard' onto windows [you already have a headboard... hmm]

CSL Tour 2011 · More Info

Maybe an ivory and casual almost gauzy fabric just to top of wall? this type fabric behind bed, but not necessary to have pattern, etc... might be 'busy'

[https://www.houzz.com/products/faux-silk-overlapping-curtain-ivory-prvw-vr~65619968[(https://www.houzz.com/products/faux-silk-overlapping-curtain-ivory-prvw-vr~65619968)

Here's 4 pieces including the semi-sheer - versatile for use at different windows / behind bed... not expensive and different colors. 96" tall.

If your room works with bed at window, Flo's with same paint color on triangular shape showing above curtains... ?

going with the Flo -- Idk if largest windows are at opposite ends or what /// Oop

https://www.houzz.com/photos/enchanted-oaks-traditional-bedroom-san-francisco-phvw-vp~1098491

photo wouldn't post - striking fabric would be focus on bed, and not much else needed.

Off topic...Oh my gosh everdebz..."Go With the Flo" !!!! Brilliant!

Flo you totally need to change your user name!

OP, as I said, the "drapes" wouldn't be nearly as overpowering as the photo I showed...and they don't need to be so full or high...

If you don't have room to move the armoire, then it's staying, so how about that small area with the octagonal window becomes a "dressing" area...you could have a cheval mirror in front of the window (won't cut off all of it I imagine) and the wall could hold scarves/necklaces/purses. OR you could have a dressing/makeup table under the window and a little fancy chair...in other words, give that spot a purpose so that the window doesn't look like the odd man out...

yes, i love creating a purpose under the octagon window. i wish i could move the bed, but i have tried and it simply doesn't fit anywhere else. love the idea of the lighter more sheer curtains. Btw, Go with the Flo is a great name.

Like most bedrooms, your bed linens will drive everything else, including paint and drapes...mull it all over while you're gone...I'll see if I can find more pics to post.

Safe trip!