Removing chain link fencing is one good way to update it! Remove shutters. Paint the house create a defined entrance, removing the old entrance overhang and columns. A Metal roof would also be good. Be sure to check out your local Habitat For Humanity Re- store. note: cracking brick could mean foundation problems or something structural. Think Katrina Cottages

Thank you for the comments! We are planning on pulling out all the landscaping along the front of the house. I completely agree that it is way too large. I think seeing all the brick on the right hand side of the house and not being able to see it on the left is part of what is making it hard for me to visualize. My husband's work schedule should allow us in the next week or so to start pulling out the bushes and I can't wait! As much as I would like to take out the trees in the front yard (they are HUGE pine trees) we are going to have to wait and save up to have them professionally removed because of their size. The windows that my husband wants to enlarge are on the end of the house where it is all siding and then on the driveway in the below image where it is all brick. The windows on the front he wants to widen more then lengthen because of the brick placement. I hadn't really thought about removing the shutters completely, so now I am curious to get them down and see what it looks like. I'm not opposed to painting the brick. Which is why I was wondering if I should paint the siding and the brick the same color. Is it better to leave the brick as is and adjust the siding and front door color?

@HALLETT & Co. The original owner added the brick planter in the late 1980’s and they’re crumbling and safety hazard. I don’t think they offer any curb appeal. Especially the long planter to the right of the door, it seems odd. The smaller one near the garage is ok but not great shape either. The tall brick stacked next to the front door is original to the home, it’s staying put. We found out my husbands best friend’s great uncle had this home built and we have confirmed those aren’t original. I feel better about doing away with them.

Interesting - I like your theory about someone homesick for New Orleans LOL. As mentioned above, porch cant really be removed without leaving scars - and an overhang much deeper than the rest of the house, which would look funny. Can the balcony be used, does it make sense to open up a room to it? Part of its oddness is that its obvious that there is no door and cant be used. Whats going on under the porch, behind the hedge? Some kind of patio? You could remove the hedge, expand that and make it into useable attractive outdoor living space - framed in a border of flowering fragrant shrubs, 1 or 2 well placed ornamental trees (ie short, placed toward the side of the house), intermixed with perennials/bulbs. You could leave a few of the evergreens - its just the solid wall of them that is so unappealing. What are the rooms on the lower level - would any of those benefit by opening up to a patio? .... or maybe it could be an actual courtyard and by that I mean a professionally designed walled space which fits architecturally with your house.... not an ugly cheap privacy fence from Menards! But then that gets to be expensive too - probably more than just removing the darn thing! Otherwise, maybe just swap out the frilly iron work for something simpler/more linear, with strong horizontal lines as is fitting for this style/era. Also changing all the white to something less high contrast - would help de-emphasize it.