good all the shutters are gone.

I would put a a narrow pergola over the garage.

While replaceing the windows,

If it were mine, I would blow out the entire front door and big floor to ceiling window unit and create a whole new entrance, ... what's that side door for?

double doors and floor to ceiling windows to fill the space.

Create a Courtyard. You have a large drive, I would see if there is space to create a drive around with a center tree and plantings. Have you considered hiring a landscape architect? It would be fun to get a professionals perspective. ... you could do it in stages if you think it is too costly.

Lovely home! Right now the huge driveway dominates everything and I don't have an easy answer for that. Given you're prepared to invest $$$$ in the landscaping, I'd hire a designer to come up with a plan than minimizes the driveway and calls attention to the house and entry. Once you have a plan, you can implement it over time. Good luck with your project.

The house is much improved without the shutters. A couple thoughts:

--The white garage doors call way too much attention to the garage instead of the house. The darker garage doors looked better. A pergola across the top would add interest.

Park Place · More Info

--The current entry doors don't suit the style. Something like this, along with larger, modern copper finish or bronze light fixtures would modernize the house as well.

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Landscaping:

Mid-Century Front Landscape - Wauwatosa, WI · More Info

Seriously consider a round version of the driveway island shown below in the middle of the driveway with stone mulch and simple plantings/grasses to break up the mass of driveway which takes up so much visual space.

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Landscaping is going to be a big part of this. As will hardscape.

I would get a local hardscaper out for some ideas. But I’d probably do over the driveway. To a lighter cement. And as small as you can go.

Add more grass.

I also think once your redoing the windows, if the interior allows, maybe add some French doors leading out to where the plant beds are. And create a flat surface for a porch.

Match garage doors to new front door.

French doors inspiration

Thanks everyone! There is a wall behind the house number to divide the entry from another room so the door cannot get much wider. I could still change the window to something larger.

The side door leads into a small mud room. The garage leads into there also. This door is. It used so it could really be removed but then we would have to match the brick or paint the entire house.

We had a co silt already with a landscaper and I am debating if I should go ahead with them for the design. I agree, it would help me visualize.

The driveway could become a bit small alone each side and still function. I like the idea of something in the middle, I would have to see if getting out of the garage would still work. I like these ideas though! Thank you everyone

Great that you've met with a designer. It's money well spent since you'll have a roadmap going forward as budget allows instead of doing things willy nilly.

Getting new front doors and doing the hardscape work will do wonders. Your house is nice as is. Painting the garage doors black like the window trim is another easy, inexpensive idea. When it’s time to redo the roof, you might consider a deep, dark gray instead of brown.
For the front door, the MCM look could bring a specific design look to the house. Matching the garage doors later on also brings a stronger design statement.

I would add a pair of medium/large planted pots, one on each side of the front door. Try power washing the concrete steps to even out the coloration.

Some ideas to consider

More front doors

Garage doors

Any input on if I should replace the windows in the same style/black? Or if I should add a single grid cross ie. making each half into 4 (not a fan of too many grid squares)?

I like the black windows and would NOT add grids. it would be far too busy along side that brick.

if you want more of a mid century vibe, go w/some of the doors Red posted above.

The driveway and hardscape will be 75% of the curb appeal. Spend the money on that, especially that driveway.

Similar home.

Before

Rendition for the after. what a diff, eh?

(this brick isn't as busy as yours, so these colors and wood tones all compliment it. You color brick is going to be tricky to work with.

similar ranch style. new door, flowerbed, I like the dark roof here.

Here's a similar large driveway. Look at the more modern garage door/front door. keep the windows large and free of grids. If you paint the brick, bring in some wood accents.

I don't know if you're up for a new roof? If that time comes, go w/a charcoal color.

what about the brick? Romabio is a lime product that is healthy for the brick and will naturally age.

Not into the mcm look? you could easily do something like this w/your home

a gable could be added and the porch extended. brick done in white