Examples of some color schemes I like. We will likely need to eventually replace the roof to match the new trim color.

What color choices does your window brand offer? It's a beautiful house.

Such a lovely house! Here are a few blogs to get you started - do you want high contrast with the beams or are you looking to minimize that detail?

https://www.thephinery.com/blogs/color-consults/gray-owl-tudor/

https://www.hunker.com/13775156/tudor-house-exterior-color-ideas

https://julieblanner.com/goodbye-yellow-brown-house/

We are looking at the Marvin Elevate windows. I am deciding between: Bronze, Pebble Gray, Cashmere and Stone White.

https://www.marvin.com/products/collections/elevate/double-hung-insert

I like some contrast. We will also remove the shutters and the window boxes as they are rotting.

Just popping in to say how much I love your charming house and that wonderful sidewalk. Tudors have a special place in my heart. :)

The second floor and entrance look twenties or thirties but the two bay windows look seventies or eighties? I would investigate redesigning the bay windows as a first step.

Wow! So beautiful house!

Some rough rendering for colors

Love the colors it is now looks like its straight out of a storybook!

Start by removing the out of place shutters. They do nothing for your house.

I would pick a window color first and have them installed. Then look at paint. No to Stone White. Bronze, Pebble Gray, or Cashmere would look good.

Are you just painting the trim or the whole house?

Painting the whole house. Agree the shutters need to go.

I'd go with stone white windows. You have a brown roof. You'll need a warm gray or taupe to not clash. You note @Celery gave you a gray roof, although re-roofing when the roof is in good shape is rarely in anyone's budget.

Your middle two inspiration pics are fantastic. I'd look at the windows available and start to find a color combo that works with them and i looks like those middle two pics. Will you be painting the brick around the door and changing the color of the walk way too?

The only window color you don't have to consider, factor into an exterior color scheme is bronze.

And I'd choose to do roof first if at all possible. Because aligning roof to existing trim color is harder. Shopping roof brands with color as first priority, function and price second/third isn't fun.

And whatever color you choose, don’t forget to factor in your lovely walkway colors, as well as the roof’s color. Tying everything together, top to bottom, will give you a beautiful result.

Maybe I should consider the Andersen Sandtone windows. Does anyone know how they look on a tudor?