Tudor is not dated. There is nothing wrong with your house. It has charm as is. Throwing 50-150K at it will never be recouped.

The color has become dingy and the dark windows look forbidding. There's some leaking so the house needs re-siding. Thanks!

Then restucco it properly with the correct drainage plane and flashing. But I doubt it needs resided in entirety. More likely it just needs the pain points paid attention to by an expert.

Yes I agree! Front windows need to be balanced, lighter color would freshen it up! Thank you :) Would a dark color be too intense if it's close to the road?

Add some more photos to your next comment from across the street. Does the front get morning sun? Sometimes you need a depth of color for the home to sink quietly into the landscape background. A lot depends on your seasons and region you reside. Are there other neighbour homes close to the street?

If the roof color is remaining, your colors will need to work with it. Benjamin Moore Copley Grey and Elephant Tusk trim in the photo below.

you bought this Tudor but you don't like it? now you want to change it into something else? no. work with what you have. Tudors are unique and awesome looking homes. I'd kill for one. Landscaping will also go a long way. you need to prune those shrubs.

Is that yard sloped towards the side of your house? obviously that needs to be addressed as Sophie mentioned.

You could do some cedar shakes if want to add some interest.

If you want to change the windows:

here's a lighter color scheme

The third photo down in Bette P's post has ideal colors for your roof. I think changing the colors to a less intense contrast will make this a very attractive house. Good luck.

Kinda looks like a 70s tudor. Not sure how you would re-side it to make it look different in that regard. I like the pictures Bette P posted. I am not crazy about the cream color with the black. Maybe paint it a grey color to update a bit? It looks like you have black or dark colored blinds inside. I would get rid of those. I would also trim down the bushes that are in front of the windows...cut them so they are just under the windows. I think a copper or metal portico would be the greatest addition. It would give it more presence and anchor the entry. I would also replace the front door.

What color is your roof? If you are not replacing it, would keep that color in mind when choosing other colors. I see too many houses with siding & roof colors that do not look good together.

I would not call this a Tudor revival, personally.

To me this looks like a fairly standard mid-century era two-story development-house plan in mock-Tudor wrapping. (There's nothing the matter with that).

So, I feel like this house could also have been detailed as a garrison colonial without the front facing peaks and jerkins, or an English arts and crafts with those details. Or a clapboard Cottage or Romantic revival as well A true, earlier Tudor revival, like most of those shown, would have more of the massing of a Tudor, which this doesn't have. In my opinion different siding could turn this into something else completely (except maybe for the jerkinheads), because that's how they made these floorplans look like different houses to begin with: variations of surface detail.

I'm also seeing a two story with some slapped on Tudor trim. Don't know what your budget can stand. Options would be:

1. 1. Fixing problem areas and repainting in colors that do not so starkly contrast with each other.
3. 1. Remove dark Tudor trim and repair stucco and then repaint.

Re side the entire house with horizontal siding and use a color palate that evokes more of an arts and crafts style home.

How much I would do and spend would also be related to how long you plan on being in the home. If it is your forever home then I would do as much as I could financially to make it the house I wanted.

I think you can add some colorful things at the backyard as you can maximize the space for outdoor play house or outdoor tables with classic touch of tables and chairs or make use of those trees to add some design or swing

Such great ideas! Thanks for giving confidence. I think a front porch and more dimension would really help it look less forbidding and more comfortable. We plan on being here for the next 20 years. The roof is a 70's brown color unfortunately and is not old so it's here to stay which will hamstring some of the color options :( I think dark gray/blue would be beautiful but might be too intense so close to the road. There's less light in the front and tons of sun in the back. A new front door and landscaping definitely needs to happen - I'm a big gardener so there will be lots of green ferns and flowers. We live in the PNW so with all this rain we need to brighten it up but not too much since there's not much clearance between the house/road.

Should add that much of my challenge is not finding houses online or in the neighborhood/city to compare it to for color ideas. But hearing that I'm not stuck with Tudor necessarily is great. Off white with light gray Tudor trim would probably be the best option if we keep it as a Tudor. Thank you.

It is charming! Change the trim color if you want... or buy another house.. that one is NICE.

Would this color/style work?

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I wouldn't call this a real Tudor, more a mish-mosh with some Tudor trim. That is why it doesn't look "right" to you (or me). Half-hearted gables, the door is wrong and lacks importance, it altogther seems not graceful.

If you don't want to pull off the faux half-timbers, you could paint them out -- make them fade into the overall siding.

You need to decide which direction you want to go -- I think there might be things you could do to "fix" the Tudor look to an extent -- changing the dark paint in the gables would be a start, maybe adding another texure (stone or brick) around the door area. As many have mentioned above, the right color scheme can make a huge difference.

My inclination would to go in a direction that might suit the overall shape of the house a bit better though.

Your roof's shade of brown is not a bad one and can work with several greens, blues, reds and, of course, neutrals including a few grays. You are lucky that you can paint which gives you infinite color choices. If you don't want the color to pop too much because you are close to the street, choose a muted tone. There are lots of gray- blues, blue-grays, green-grays that would lighten up the house but not be too strong.

When was the house built? Are you replacing all the windows at this point?

If you will be removing all the stucco siding and every bit of Tudor-type trim, you do have the opportunity to change the style. Consider hiring an architect after you have gathered some inspiration photos of houses you really love. It could easily go more Craftsman.

Any thing you can do about the leaves in the gutters, maybe gutter guards, may help with water infiltration. Some judicious tree removal may be an option, too. When it comes to leaves in gutters, an ounce of prevention is worth a pound of cure.

Congrats on the new house! The most pressing issue for you should be to address the sloped side yard. Perhaps the photo makes it look worse than it really is? You probably already know this, but, the staining is caused by rain hitting the ground and flinging dirt up onto the siding. It probably needs to be regraded to slope away from the house and that will likely necessitate a low wall around the trees. No point in painting until you fix the drainage around the house.