Do not consider painting with acrylic paint. It will peel. Use masonry paint or limewash which allows the brick to breathe. To make it more interesting you can LimeWash the brick which allows some of the brick colors through the application. It add a unique vintage touch to the home.

I like your brick colour. You can easily damage brick and mortar with a power washer. My city (Toronto) is mostly brick houses and nobody ever washes their brick, much less power washes it. I would choose a black roof and white trim.

I agree with the above comment re whitewash over paint. If you go that route.
But I think I’d leave the brick so you can spend more elsewhere.
Black or navy blue trim would look very nice.

Add some outdoor lighting
And focus on landscaping and hardscaping
(I like how the third picture has that cement surround, I’d probably do it just on the ground level and leave the rest grassy ...)

Awesome awesome home!!

If you end up planting something on the sloped portions without terracing, you need something that takes dryness, since the water runs right off. Look for plants in your climate zone that are suitable for xeriscaping.

If you want to level off some portions, I notice that your yard slopes from side to side as well as from front to back. So your wall would be taller near the stairs. A curved terracing wall is much more interesting visually than the straight ones you show in your mock ups, and will probably suit your slope better too.

Curved stone retaining walls and huge boulders on hill · More Info

Your brick is too nice to paint. I hate white trim with brick so I would vote for an olive grey on all the trim. Are you replacing the vinyl windows? If so six over one would probably be more period based on that charming attic window. Why take down carport? Yes the house needs great landscaping...

Please keep that gorgeous brick as is! I love @HALLETT & Co. suggestion for olive grey trim. I completely agree the brick would do well with a darker accent trim vs the current white. I think charcoal gray also would work well. I think the black roof is classic especially with the brick.

I'm sad that you don't think your house is much to look at. I think it is a beautiful house as it is. It could use some spruced up landscaping and might benefit from a different color of trim. But the overall architecture and brick is really beautiful.

I love the look of a front yard with small terraces supported with stacked stone walls. I think that would look really lovely for your house.

I'd leave the brick alone. You could paint the trim a dark sage green or black. But I think most of the sprucing up should be in the form of landscaping with colorful perennials, roses, and hanging flower baskets.

Remove the dense boxwood hedges and replace with hydrangea, or azalea, or rhododendron. Do a terraced scape on that rise near the sidewalk and plant a bunch of day lilies and a mix of other flowers.

Some inspiration:

Heavy Timber Tudor · More Info

Good Garden's Own Backyard · More Info

Hamptons Hydrangeas · More Info

The hedge needs to go. The brick will be fine if cleaned up. You may need it re-pointed, If the house faces north, hydrangeas will do well. If you want year round greenery, they won't.

the brick isn't the issue, the landscape is.

Your hedge HAS to GO!! seriously. it blocks the front of the house and does nothing to enhance the yard.

spend the money and hire a landscape designer. 90% of your curb appeal will come from that.

consider adding some bricks to the cement steps, and flower beds along the side. you can round off the slope of the grass, remove your hedge, do some nice flower beds, a tree, etc.

Think English style cottage gardens. roses, small shrubs, pots, (you need a landscaper person for this)

the other 10 percent, the roof (I'd do a black or charcoal), replace those windows if you can (the glaring white just doesn't go w/this brick tudor) and try your Urbane Bronze on the trim.

Normally these homes had wood doors. if you can't do that, then consider painting yours black or the bronze.

I don't mind the black windows, and black trim on your mock up.

Here's one similar to yours with a very dark trim and windows. (if yours aren't vinyl, paint them)

more of a dark blue/charcoal color and a warmer slate-brown color roof.

You could do a type of Schmear or heavy mortar treatment over the brick.

And if you want a hedge in front, do the hedges like this!

This is one of my favorite brick tudors. notice the door, the trim color and most of all, the landscaping.

another one w/landscaping ideas. flower beds and your lawn will be the main appeal

Similar style. this is a warmer charcoal roof, the windows and the trim are a medium warm gray color, as is the door. This landscape is rather blah

Urbane bronze would be similar to this one. notice the wood door.

if you want to paint the brick, go w/Romabio Masonry (not the Classico).

Here's a brick tudor style done in a creamy white, soft greige trim/windows and aqua door. Notice the slate walkway. you could easily tile your cement walkway w/a flagstone or slate tile. really looks better than bare concrete.

This before and after brick tudor-style was done w/a custom color in Romabio Masonry.

look into Faux-Slate roof tiles. they work w/your style. comes in many colors

http://www.create-enjoy.com/2021/04/home-tour-classic-brick-tudor-revival.html

Cute house! I like the color of your brick and would save my money for other projects. I could see a deep blue-green for the front door or perhaps a light aqua. Go ahead and choose your replacement roofing material and then pick your coordinating paint. Most of the tudors in my area have 6 over 6 windows.

When you plan your new landscaping, put in handrails for those stairs.  Even if you don't need them now, they will be helpful for older visitors.

Here are some ideas:

Love the stone wall shown above.

I second the suggestion to add some railings to the steps area. Helpful for anyone who might be a bit unsteady on steps whether dry or wet/icy - older folks, pregnant ladies, people with visual challenges, anyone who might have one glass of wine too many...

Awesome feedback guys! Love all the ideas and tips here. This has pretty much helped us make up our minds on leaving the brick as is and going with a darker trim color. @Dig Doug's Designs, thanks a lot for that mockup, looks super! Its really wild how much landscaping can do to enhance a home. I forgot to say in my original post, but the hedge was trimmed way down right after we bought back in May. They are Azaleas and I hope we will see some blooms in the Spring. Still deciding if we want to keep them there or maybe just remove a few to make room for other plants. The terracing looks awesome as expected! Anyone have any experience DIYing terraces?

@HALLETT & Co., I think for now the vinyl windows would stay given our budget and allocating money elsewhere. I know its not recommended however we are thinking we would paint the vinyl windows making them the same color as the trim. Also, the carport is dilapidated and rotting so it has to come down. The carport is also a little too tight to fit modern cars with opening the doors so our plan is to take it down keeping the brick columns and replace with a pergola to create a patio sitting area.