It can be a tough decision to paint trim however, in this space I think I would paint the trim around the windows, the fireplace, base and cove molding. I would leave the stairs and the bookshelves at the top of the stairs for now, live with it for a while. Have you decided on a wall color? You have tons of natural light, you could go with a more saturated color for sure, like an Agreeable Grey, Repose Grey from SW.
Best of Luck.

@Tara Gallagher Thank you for the suggestions! I have not decided on a wall color, but was actually considering Agreeable Grey or Accessible Beige from SW. I used them both in my previous home and really loved them.

Your trim (all of it ) is gorgeous. I am not against painting wood trim, as some looks so much better painted, but, your house, like a few others that I see on here, has beautiful trim. Your whole house looks very well maintained, and cared for. Your trim, appears to be quality wood. I wouldnt paint any of it. Why make it look just like everyone elses house, when you have something that is already beautiful.

For trim, has anyone used SW emerald urethane tinted in high reflective white? Asking for a friend!

Gorgeous house. Loads of potential!!
I would keep some and paint some.
The trim I keep I would stain a bit deeper of a brown. I would paint all baseboards and molding white.
Remove the FP woodwork. Do something more updated.
....

And keep:

the stairs
the big windows
the doorway from the front door and the doorway between the kitchen and LR wood.
....

What do you plan to do with the flooring in the LR? What’s underneath the carpet? I might consider adding (maybe you can use the extra already wood stained molding and replace that with white)
Some molding/ wainscoting work to the fireplace wall.
I’m picturing that whole wall deep wood molding. With a cement fireplace surround.

Thank you for the suggestions, everyone

@HU-187528210 I really like the idea of the cement fireplace and will be looking for inspiration pictures this evening. There's just subfloor under the carpet, but we are considering extending the hardwood into that room as well and at the very least replacing it with better carpeting.

@cat_ky thank you for the kind words. I purchased the house from the original owners and they did a great job maintaining it while raising 4 kids. I'm lucky to get to focus on the fun cosmetic things to make it more modern and our own as we plan to be here for many years.

Thank you for the kind advice, @cat_ky. I think that's a sound strategy for the first year in the house. It can be easy to get sucked in and want to do everything.

I agree. Live in the house for a year or ? before making somewhat irreversible changes. in my prevous home my initial thoughts of what i wanted changed dramatically a few years later when doing a major remodel. Btw … the trim above the fireplace would bother me, I’d either remove, remodel it or paint it?

@K Laurence Are you referring to the decorative white trim about the fireplace? If so, I agree and already removed it :-) Thank you for the feedback!

Anyone have thoughts on the window muntins? Should they stay or go?

I would remove them , but that’s a personal preference.

Can we see a pic of the fireplace without the white trim pieces? I think maybe the overmantle may need to go as well. I would leave the grills in the windows, but That’s just personal preference.

You need to choose the right tone to go with oak so here's a link. https://jillianlare.com/coordinating-paint-colors-oak-trim/ and a photo

How to Pick the Right Paint Color to Go with Your Honey Oak Trim · More Info

I would leave the grills in the window too. Your house is large, and very spacious. Those grills actually make it look a bit cosier.

Wow! This is gorgeous and wood trim is coming back in style. I wouldnt paint any of it. If budget was unlimited I would want it a darker stain color but that would be very expensive. I love the bookcases and arched windows. Just gorgeous. Things I would look at changing are to replace the carpet with wood and a nice large area rug. I would update the fireplace by running stone all the way up. I would also change the pendant lighting over the kitchen island. What a beautiful home you are so lucky!

I would leave the wood trim as is and muntin bars, but of course get some big time colour on those walls, you have so much window acreage you could go as dark or saturated colour as you want. Your pale green carpet makes me wonder what some level of Prussian green or Prussian blue would do for your huge space. Colour (color- I am in Canada) and all that light will let you be dramatic, fun, or simply elegant and sophisticated, paint some test areas to see what the paint looks like on your wall, not just a sample chip. Again with all your window light I would use a flat paint. Fresh paint can make a big visual improvement for not that much expense and is easily changed later, enjoy your fantastic new home.

I agree with COLOR on the walls. That’s a small thing you can do now and if you change your mind 6 months down the road, it’s easy to change. Green is a great suggestion!

Leave the wood trim alone for now. It’s a beautiful home. Everything doesn’t always need ’updating.’ If everybody always updated everything, we wouldn’t have the stately turn-of-the-century Victorians that people go nuts over.

Everyone wants to start with paint but really it should be last on the list. Really any paint color goes with wood floors but only certain colors look GREAT with your upholstered items/rugs/decor. Good advice to move in with your stuff and live with it for awhile - and then post pics to get best advice.

I am not a decorator but to me it looks very busy and choppy. It is very 80’s for sure. I would paint the stair handrails just to blend them out. This is not one of those all or nothing situations. I would begin with removing some bare wood with paint until you get the balance you are striving for.

I agree with Yayagal……add color to the walls. Our main home has trim very similar to yours ( and hardwood throughout). i have found that pale wall colors give too much contrast and make the rooms look washed out. Add a paint color with a little depth, place your furnture, hang your art, add accessories, and then wait to see how you feel.

You have purchased a very beautiful house!

Just my 2 cents is definitely go with the grilles on the windows. I would redo the fireplace. At the very least remove the top piece and add a cool mirror. I would definitely add some color to the walls, maybe a darker shade of whatever color you choose to 1 wall for contrast/accent. I would live the oak trim for a bit and if it still feels like too much I would consider changing all the railing around the stairs to something different. I would also update foyer and kitchen light fixtures. I love the upstairs bookcases and the round window. It’s already a beautiful home and just needs a little updating.

You have a beautiful home! I have owned two homes that I updated and currently in a new home for the first time. I can say with experience it takes time and patience to update a home and get to know what you like and don’t like in materials. I like the ideas of painting the trim. The fireplace would look great with a chevron pattern possibly in wood or tile. Have you considered changing the stair spindles to a contemporary iron or glass panels. Just some ideas to add to others. Enjoy the process!!!

Personally, I am one of those people who think it is sinful to cover beautiful natural features like trims, and fireplace boulders, I know this is not the current trend, but hold firm in my opinion.

I love your house it has some classic look to it. but if you want to paint the trims, it almost looks like you have to match the whole thing. Stair rails, all the baseboards and doors. Moldings, fire place and even bookshelves. but i would Avoid using stark White color personally. i would use a soft cream white or some greyhie color that has more beige color in it to give that old charm that goes with warm tone. since the floor has alot of orange in it, i would use warm tone paint in everything. yet still look updated but not the popular farm house look everyone go for. i am a fan of it but this space is not for that style to me. It looks more comparable with something like updated old fabulous new york loft or updated DC manor. great windows and stairs! i wouldnt ruin the look with urban style.

I would also wait awhile. Your home looks quite lovely “as is”❣️Your space is so grand and I think the wooden trimming accents it beautifully.

Leave the wood as it is...........paint walls a darker shade so that the wood won't look so stark. In a few years, you will be sorry if you paint your lovely oak! It is lovely! Just my 2 cents.

I don't know if anyone else has mentioned it but I think the crown moldings are to big for the ceiling height in all areas except the great room. There are only a couple of inches between the tops of doorways and the molding, It's just too much wood, it's a bit overwhelming and dominates the rooms. I would paint it white and consider removing or downsizing the lower ceiling areas. You could try an editing program on your photos to see the differences. Good luck!

We have moved many times and owned a number of homes across the country. They varied in age from fairly new to 100 years old. I did renovations on all of them. They all sold relatively quickly and the comments I received was that the houses had a fresh look regardless of age. I like clean simple lines, that update, yet still nod to the character of the home. I would paint out all the wood trim with a semi gloss white except for the doors.Keep the walls light and update the fireplace. It would give the house a fresher more modern look that would blend easily with the more traditional staircase. Continuing the wood floor would definitely upgrade the look and I would replace the staircase runner with a more expensive interesting carpet or remove altogether. I like the open feel of the windows without the mullions, especially if there are nice views, but that is a matter of personal preference. Sometimes, they can cheapen the look of the window when they are not true divided light. It is an impressive room and I’m sure whatever you decide will look good.

Do not paint over any of the wood trim. Will be very difficult to strip when/if you change your mind. The dark wood stands out now, as there is so much contrast between the dark wood and the off-white paint there now. Put the window muntins back in . Whole main level needs color. Try a rich saturated shade on one wall. It will just look like an accent wall until you decide if it's the right shade for you. Color - add a large bright accent rug over the existing wall-to-wall carpet for now. Add a couple of arm chairs in colored fabrics, and some accent pillow for the 2 sofas. I love the library on the 2nd floor gallery. Think of a major redesign/rebuild of the fireplace wall.

If you decide to paint the walls, also paint the crown around your ceiling white. Even that little change will make it look updated.

Please don't paint the oak!! All-white has been done to death. Plus white trim is a good cheat for chipboard, don't use it to hide beautiful wood.
I see what people mean about the "mid-brown" colour of varnish but I think it's the magnolia cream that's dating the room, not the wood. Changing the colour to deep green/blue would make the wood feel warm and give it more depth. I would avoid grey, not classic colour palette and I think it would clash with the wood.
Agree with the suggestion to do minimum for a year, very difficult to un-do changes!! But longer term this could be a beautiful drawing room with rich colours and textures, then that cosy study upstairs. Perfect

I suggest considering removing whatever is above the fireplace; it is rather fussy along with all the windows and the semicircles above them. I also do not think grey on the walls in any way would enhance the woodwork if you want to keep the wood as it is. Have you considered removing the carpet and putting hardwood like the rest of the floors?

The windows are what date the room to the 90's so I would choose a wall colour and then paint the trim in the same colour in a semi gloss. While it is nice to have a lot of light I find the windows, in addition to being dated, make the room fussy, like the woodwork above the fireplace. My point is, the room should be coheisve so you can decorate with your furniture and decor making the statment rather than the trim and windows stealing the show. Super long curtains would also help to take away from the dated windows. I am assuming you do not want to replace the windows which would e super expensive to do.

We also purchased a custom 1990's home last year -- we are still unpacking! Our single-story house has 12' ceilings in the 'public' rooms, no crown molding, and shiny brass "gold" metal hanging lamps and accents throughout. I hated the brass and before ever spending a night in the house, I spent $2000 (on a good sale!) on chandeliers and lamps in satin nickel. Ten months later, those light fixtures are still in their boxes in the garage! Some of the "gold" is going to be too costly and fussy to replace, so now I'm thinking I only want to replace the lamps that don't suit our uses of specific rooms, and to go with maybe antique brass to blend with the polished items.

That doesn't apply to your situation, except to validate the people who said wait and see! Here's what *I* see: (1) The crown molding is pressing everything down! I would paint it all the color of the wall beneath, to raise the ceilings visually. That means DON'T paint the crown molding in the all-wood library upstairs. (2) Leave the mullions/grills off the windows; don't paint the rest of the oak until you live with it some months. Adding a (3) after looking at the photos some more: Go ahead and paint the oak around the fireplace, it is that awful. Are those DOILIES??? Paint it the color of the wall and hope it disappears into it, until you find a picture somewhere of what you do want after living with it. Maybe just the marble/stone part and some big art or textile above?

Oh, and if you choose to paint before moving in, in the previous house we re-did we used Benjamin Moore's Brandy Cream OC-4 on all the walls (and crown molding, and chair-rails in a couple rooms). Actually it was Sherwin Williams paint made to match OC-4, and it acted like a "full spectrum" paint, slightly changing according to the lighting... which would be wonderful with the big windows!

Generally good advice to move in & live with it as is for a while. Exception though is the fireplace. I would never learn to love it as is and would pare everything back to the first mantel before I moved in. The stacked mantels & arch are too much and, IMO, the one thing that is anchoring the room in the 90's.

Another thought - the wood trim will not seem so overpowering after you choose window treatments. Drapery panels with rich tones, and a pattern will add lots of interest to the room. Use some of the same fabric - or companion fabrics - for throw pillow on the sofas, and perhaps an upholstered armchair. Select paint colors from the fabric, and not the other way around. Fabric sample books will have coordinated fabrics in a color group - perhaps a print, then several variations of plaids and stripes. Better fabric shops will have these - look without paying a fee. Also browse online.