We'll do better with a closeup pic, but no shrub ever objects to a nice feeding with Milorganite or another organic feeding in spring at the bag rate or a little greater. Don't overdo--shrubs and trees aren't big feeders or usually particularly fast growers--but once a year? Sure.

And you'll be feeding them incidentally every time you feed the lawn. Their root systems spread wider than their greenery.

Ok when it’s light out, I will take a closer pic.

I agree. A little organic fertilizer, a nice layer of compost and water as needed. IOW, baby them. Cut out any dead branches but otherwise I'd wait a year to do any serious pruning. Congratulations on your new home -- it's very cute!

Thank you so much, we are so excited about the house! This is all great advice I will do all of it.

It's an awesome place.

As an incidental, it looks like a northern lawn (fescue, rye, and/or bluegrass). Which is in desperate need of a feeding as well. Fortunately, now is the right time for that (Memorial Day is actually the exactly-recommended time).

If this is wrong and it turns out you're in Atlanta or something, pipe up. :-)

Any good lawn food that's high in nitrogen (the first number) is appropriate. I tend to choose an off brand because you pay for the name, so I'll choose Vigoro over Scotts. And I actually use fertilizer-grade urea in a plain brown bag labeled "Urea. Fertilizer Grade" most of the time. :-)

Just follow the bag instructions for application rates.

After that, feed on Labor Day, October 1, and when the grass is green, but when you've done the last cut and the lawn's not growing (usually November for most of us).

And always mulch mow as high as you can stand it...

If you post close ups we can tell you what the shrubs are.

I will be posting close ups! Also, I’m in FL.

I put pictures of the shrubs and then the third picture is the lawn. First picture is of the shrub that’s doing well. Thanks for everyone’s input!

Southern lawns will tend to want feeding monthly throughout the season, but somebody who can identify what the grass is will have to do so; there's some variance.

Thanks everyone! So I should wait until next year to actually prune? Because they are very uneven.

Boxwood can technically be pruned any time, although the period just before frost is best avoided up here (for you that's not so much of an issue).

Spring is the best time for a pittosporum, and for you, that's right now. The reason there being that pruning later may, again, cause easily winter-damaged growth that doesn't have time to harden. For you? Maybe not so much of an issue, but it still might be.

So in both cases, I'd say you're good to go right now. Feed right after to encourage repairing of the wounds you just made and to start new growth, but other than that, have at it.

If you're in quite far northern Florida, avoid pruning later in the year to keep younger, softer growth from happening just before colder weather sets in. You might get a little winter kill, although I find it to be unlikely in your climate (even younger growth on boxwood up here tends to be OK and I'm in the foothills of the Pocono mountains where we ski).

I can't speak to pittosporum as I have no direct experience, but with the hardiness zones I see (8 to 12), it's going to be a lot more sensitive than boxwood (6 to 9, some to 4).

Thanks for the input. We are in North Florida and we may see a few below freezing nights. So, I will take the advice of when to prune in regards to frost. Thank you again for the amazing advice.

Other than getting rid of a lot of the leaves, what can I do to prune? I know I’m supposed to get rid of the branches that cross, there are just so many as it looks like these may have never been pruned. I pruned one of them and it took so much volume away....

The general rule is to remove no more than 1/3 of the plant each year. Here's an excellent publication from Purdue University that might help you decide how to proceed. Good luck! https://www.extension.purdue.edu/extmedia/HO/HO-4-W.pdf

in one of the pix.. i see the utilities ... call miss dig.. and have them come mark all such.. and take pix for future reference ... out 6 to 8 feet into the lawn ...

too many peeps plant thing to hide such .. and then you are left to deal with them.. do no significant digging there unless supremely careful ...

if i were you.. i would go full bore on the lawn .. and once you improve that .. then start looking at the foundation plantings ... imo.. you can improve the front of the house 90% with the lawn ... maybe work on the beds themselves.. defining edges.. mulch.. weed removal ... etc ...

and in the mean time.. while you are doing what need be done in the house ... by fall you can start working on the exterior garden ...

just because you want to plant things in july/august.. doesnt relaly mean its a good time to plant .. especially the future south you go ...

of course.. if you hire it all all .. pro's can do all kinds of things for the right amount of money ...

and the most important thing i learned with my first house.. just listen to us.. and simply get rid of all the mistakes the prior owners planted .. it took me 5 years to realize that wisdom ... if the prior owner knew what the heck they were doing.. you would be left with this mess .... they are not children.. or the former owners children.. just get rid of problems .. if you decide they are such.. after your research ...

ken

btw: think about trees out in the lawn ... with tree time.. which is counted in decades .. we consider trees the backbones of the garden .. plan and get those in this fall or winter ... imo ...

The utilities is a cable box. Yes I am consulting experts and trying not to make mistakes for sure....hopefully I can learn from you all before I make my own! Thank you!