I think you have a real diamond in the rough there. I'm glad you are looking to bring out the inherent goodness in this home. You have already done quite a bit of landscaping work removing the big dead bushes in front of your home and it shows much better.

The very first thing that jumps out at me is the driveway leading up to the converted room where the bench is now. I think if you remove that broken part of the drive the front of your home will be much better. Take it all the way down to where the V starts so it looks like you only have one driveway. You might not be able to do that right away. But if you could, a great MCM type driveway looks like this

Or if you want to go a little bit more eco friendly you can go in this direction - it is a permeable driveway (below)

I like white siding but I don't like brick all black or all, white with natural grasses and cool wood front door

The driveway leading into a wall (the bench) is odd. Depending on whether you use it (for cars) I’d either dig it out, or at least get a good 4’ or so of garden at the end, so the drive doesn’t butt into the house.

The siding’s not so bad, although I’d paint it to contrast less with the brick.

I’d put my money into new windows. They will freshen up the house and make it look less commercial.

I’d also get some landscaping beneath the window furthest right, as it’s so small and the siding patch does look a bit odd under there.

Sorry, I meant the TWO right-most windows.

If it is too much to do the entire driveway like I posted in the first pic (too much time or $$), then do that iconic style with a walkway, like this, right to your front door:

Denita- yes! I totally agree with the driveway leading to the wall. It is one of many ideas that has came up and taken the back seat to others (probably because it's a larger project). But love this idea! In fact, I am hoping that one day we will park around back of our house instead of in the front-- hoping that it will look so incredible one day that we will scoff at the idea of parking our cars in front of our house! That will take some time, but for now I love the idea of getting rid of that driveway space.

I think there's too much of a contrast with the white and brick...I'm pretty sure you could paint that easily to try on another color.

I would love to see a brighter color on the front door, too..

.It's a great place and congrats

jpp221- totally agree. The windows were one of the first things I decided that threw me off about the house. As we work more in the front, we will probably replace the front windows first and have the back and side windows follow. Thank you for validating my concerns over the windows!

do the driveway first. its really your biggest problem. the rest is just hand waving.

this is our previous home. the living room (on the left) used to be a 2 car garage...and while there are always more fun things to spend the budget on, getting rid of the driveway was critical to how the house looked in the end.

Thanks to all!

What a lovely house and setting to work with !
Love the sidewalk idea with the offset cement steps floating on the stone base ! But will that work in your climate ?
Can you find a nursery that offers free design plans ? The plan could include driveway and sidewalk plans too. Having a good vision on paper with a dream list will help you decide what task to tackle next when you have the time . It might also help keep you from doing some jobs twice !
For a few quick fixes to draw your focus as you drive in and until you get the bigger jobs finished - try the bench under the tree or to the right side of the yard nearer the small
windows , vertical bigger bold house numbers to the right of the front door and two planters full of flowers at the base of your steps. Love your new front door !
Have fun.. it looks like you will be happy with each task you complete .

Keep the white on the fascia and in the door area. Paint the rest a muted warm grey.

to start new windows and new driveway

Chiflipper- thank you so much! The far left window is an enclosed carport unfortunately so there is a step down. Due to the angled ceilings, I'm not sure we could adjust without spending lots of money. However, it is something that we're thinking of doing something different! Just not sure what...

I like the white with the brick. The thing that bothers me is the odd foundation. I would paint sections in the color of the brick. Then add simple low landscaping.

The tree near the drive needs to have it's canopy raised so it does not hide the house.

I like the pink flamingo and also like the door color.

By any chance was the seller the original owner? Do they have any old photos? Wondering if the windows went up to the roofline and down low where the siding is now. Similar to this photo. You need more glass.
Have an experienced arborist look at your tree. Any pruning to raise the canopy must be very specific or it will be ruined.

I don't love the red painted brick (my opinion). I just googled "red brick to white painted brick exterior" and Google images has tons of inspo ideas!

I also wonder if the windows were originally much larger and the siding was an add on when windows had to be replaced and the original size wasn't cost effective.
But mostly I am interested in this because Pensacola I where I was born and mostly raised. :) I just came back from there for a visit with my parents. There are a LOT of areas in Pensacola that could use some massive TLC and I'm glad there are people like you wanting to make an investment. Sadly, my parents' home is in a VERY crime ridden area, my parents will never recoup what my dad has put into their home, though he did it all with his own two hands and knew it was only for their enjoyment.

Oh, to answer your question... the odd driveway is what screams at me when I look at the photo. I know that was formerly a garage turned into a living space (the same thing was done to my parents' home before they bought it) but it looks unfinished still with the driveway leading right up to it and another one veering off like that.

You have a beautiful house! So much potential.

There are a lot of great suggestions here but to answer your question, I think the cracked driveway and overall landscaping is the first thing I noticed. I think that would make the bigger impact and then you can move onto some of the other things you mentioned.

Anything you do will be diminished by the driveway. Do that first. I'm guessing everything else will look much better