I think I'd also check out something with a bit more brown to it than the grays have. Drawing from the look of a weathered thatched roof to pick up on the cool brown of the trim and connect more with the warm brown stone. Also since you're considering moving from the cool white to a warmer colored stucco. Beautiful home! Have always admired the tudors.

The overall look of your house is Tudor, but it has a lot of other elements tacked on that make it a mix of different styles. Thank the builder gods that you don't have a humongous double garage facing the front. Do not paint stone or brick or you'll be stuck with maintenance forever. Do not add shutters, which will add yet another style element to this blend of different styles. (The house below does have a double pair, though, if you're bent on them.) I'm not sure you can "update" something that doesn't have a single style. The current color actually does pull the stone and brick together. If you want the Tudor style to stand out, them do what Housson suggests picking a shade of the roof color for the timbers. Your stone entrance could use a little more drama with much larger light sconces. It's a shame the landscaping doesn't enhance the house as much as it could. A curved walkway farther out so that you could have more dramatic planting beds would have set off the house more impressively. What you have is fine but more suited to a smaller house.

Well this is a very good example of why downspouts shouldn't be painted out as trim- they are not architectural elements and shouldn't be highlighted as such. The big problem here is that the façade (front) of the house was remodeled but the original brick and siding was left on the side, so you're seeing a mishmash and all of these elements would too much for me to think through, I have the same concerns you have so I'd keep looking for another house, you don't need to settle for something you don't like.

I had to post an after picture here — I ended up getting rid of all of the ivy last summer and all the old shrubbery. The old shrubbery was replaced with boxwood in front and bobo hydrangea behind it. I took the advice to not detract from the architecture by keeping the plants very short on the left side. The ivy stayed away in the larger bed so I planted 10 hydrangea last fall—little lime, invincibelle, little quick fire, and ruby slippers. All of them are currently leafing out except the ruby slippers! We ended up having our roof replaced (which I was not expecting or I would have waited to plant until this year). The invincibelle pretty much got stomped to the ground from the roofers but is still showing some leaves so I’m hopeful. The ruby slippers unfortunately I think is gone. I also planted a few ferns, couple Siberian iris, a few azaleas. And a ton of tulips and daffodils (I will pull all the tulips when they are done). I need to have it professionally edged (I’m terrible at edging) and fill in more grass but I am very pleased so far! The first pic is the before, last fall, and then this spring. I am still finding little shoots of the ivy of course but it is amazing to think that all that was in that bed before was the ivy! The tree trimming also really helped!