Here are some photos showing the tile and trim. There is white crown molding in two rooms with wood baseboards and wood crown molding in the living room.

I'm with Apple_pie. If you don't want to paint the fireplace or bookcases, then it makes sense to keep the windows wood. Keep it cohesive.

id do white or black windows. if you keep the trim wood, leave the around the window wood. i I know that you go w not want to paint the fireplace or shelves, but with the fireplace, shelving and tile, you have to too many diff patterns and different colors. Something has got to go

The pictures you posted show SO many beautiful, classic features! Would love to see some of your exterior as well. I like both the tile and wood flooring. Do you plan to have the wood floors refinished? In the pictures where you can see the kitchen cabinets, they appear to be an 80's style oak veneer. If and when you do the kitchen, does the tile go under cabinets that might be moved or eliminated?

Even if you do a few windows immediately, and the rest in phases, you need a "big picture" plan before you start. If it were me, I would do mostly painted trim, using a soft white from the tile, and still have the beautiful wood floors. And maybe do a combination painted/wood on the stairs. Lots of ways to go!

Is it possible to paint the window sashes in the future if I go with wood now and not look terrible? I agree that it is too many finishes, the tile will be replaced with hardwood eventually and my husband loves the fireplace and bookshelves as is. The thing that confuses me most is the current mix of white and stained molding.

Agree your home is just beautiful. I personally love the floors, the builtins, and everything else. I would be happy to move in! I agree, wood for the window trim. Congratulations!

Oh, as to updating-- I had a home with similar finishes, and what I did to get a more modern look was to change out several light fixtures, paint walls with a nice creamy white, added a beautiful area rug, beautiful artwork, new window treatments, and just generally styled through furnishings, a nice sheepskin throw over the back of the chair, etc. It was very simple to style the home for a more modern look while maintaining the original character. I do try and carry a few colors throughout a home to provide some continuity. Hope that helps!

We had a window in our kitchen. We changed almost every finish, but millwork was a rabbit hole I wasn’t prepared to go down yet. I chose black with wood. I can paint the sill later if we change the trim.

Since the crown in the dining room is white, you can paint the rest. It will stand out a lot less. Same with the bookshelves. They aren’t particularly heirloom quality, so to update the room I would pain them to blend with the walls or a great color accent. You could also paper the backs for some lovely drama.

I’d wait to see how you feel about the brick after you live with it for a while. but get some high heat spray paint (bonding primer too) and paint the brass black black.

ps, the window is from Kolbe.

Well, anything is possible. But there is an order to doing things, that in the long run, is a much better process, and less expensive, than doing things piece meal. Are you planning a "room by room" update? A major whole house remodel? Or just fresh decorating, and keeping things mostly the same?

Your windows are part painted, part stained wood...are they all this way?

Those are probably partly vinyl clad. It was an unfortunate era for houses.

We would like to remodel the whole house room by room as we enjoy doing most of the work ourselves. Refinishing the wood floors is on my list after my toddler exits the hell on wheels stage. I don't believe the tile is under the kitchen cabinets, I definitely want to change the kitchen layout. The roof, living room windows, and kitchen appliances are damaged and need replaced this year. I also need to replace all the bathroom sinks because they are not kid friendly. I'm considering putting in more substantial baseboards as the current ones seem very cheap compared to the crown. I agree with updating all the lighting and adding updates through furniture and decor for now. Thank you all for the advice! It helps to have outside opinions.

Yikes, I see you definitely have to prioritize. Good luck.