Good for you for rehabilitating this home. I’m not a fan of very dark colors as they can fade.

So, the side of the house is the front of the road and where you pull in?

Then, go around for the front door?

What type of home--single family, apartments, duplex? And one last question, are the huge windows above the entry door/porch area part of an enclosed porch that can be removed or is that area now a renovated room? Thanks

This house could be lovely but if it were mine I'd replace all of the mismatched windows with the long narrow type of windows that it already has. I'd also replace the large picture windows in the front with matching single width windows and beef up the porch posts. Good luck.

What is the budget??? I would have the front porch look at first, it may have to be shored up. Then windows - I would have all match. Probably the tall skinny ones where appropriate. No shutters. Paint would be after all the construction is done. Landscaping last. I find a way to have all those barrels in a storage shed

It appears a new porch has recently been added as a front porch, however, if that pic is what you see from the road, then, in addition to a horizontal line to divide that tall wall facing the road needed for curb appeal, you may want to consider recreating your front entry.

For curb appeal and practical use, wrap the roof* of that existing porch (that is on the left side) around the corner to a point that is right of the small window but left of the utility pipe/wire.

(You could add lattice at the right end of the porch to block the visual of the utility post and back yard while enjoying the new porch and/or entertaining.)

If you are wrapping around both porch roof and floor, then you could define this as your front porch by putting your steps on the left end of your new porch in line with and the width of the existing front porch so they lead directly toward the part of the porch where there is an entry door.

https://www.google.com/search?q=wrap+around+porch+with+corner+steps&client=firefox-b-1-d&tbm=isch&source=iu&ictx=1&fir=HjE-juGeXBycPM%252CuVjqJMAnUwXBXM%252C_&vet=1&usg=AI4_-kSSSe9G135auHapd4ZFRa3GOX_zAA&sa=X&ved=2ahUKEwjjsKnnqK_qAhUtoHIEHVqHAV4Q9QEwAXoECAoQFw&biw=1366&bih=654#imgrc=HjE-juGeXBycPM

Another option for now or later: You could enclose that porch now in front of the entry door to use that space as a new foyer. You could move your entry door (and the window(s) beside/above/around it) to the wall of the newly enclosed space that is facing the road -- creating that "front wall" of your new foyer to be in line with the rest of the "front wall" of the house facing the road.

[Would keep that potential change in mind as you space posts for a new wrap around front porch.]

[Would make front porch posts more substantial looking, wrapping them with treated boards before painting them.]

This is a pleasant blue color and you might want to consider the corner steps for a wrap around porch:

https://extremehowto.com/install-column-wraps-for-a-stylish-front-porch/

If a full porch, roof and floor, seems over budget for now, there is a reason I put an asterisk by the word "roof": Even if you cannot enclose the existing porch as a foyer, and/or even if you cannot wrap both the porch floor and roof around the corner, perhaps you could still wrap an extended porch roof around the corner.

If you extended the current en try porch roof to cover the existing steps and several feet in front of it, then by wrapping the resulting extended roof around the corner and along the wall facing the road, you'd be covering a ground floor space all the way from steps to about half way across the tall wall that faces the road. You'd need to use taller posts. In lieu of a porch floor, you could add pavers with grass/ground cover between them beneath the wrap around roof .

You could also plant a green privacy hedge between that porch and road to create a great outdoor space as well as the horizontal line/feature your tall blank wall facing the road needs.

You could always add a raised porch floor later.

Can you tear some if it down? Less is more.

Is this is a one family or a multi-family?

We need alot more info and so Cathy where are you?

Research city records for information on the home and how it may have looked originally. Is that an original transom above the front door? The plate glass windows, the deck materials used for porches, the overhanging visual weight of that roof top addition to the porch, the silly builder grade front door are all bringing the house down. I hope the city hasn't given you some kind of outrageous deadline for accomplishing this feat!