I would start with the basics...fresh coat of paint, darker roof and renewed landscaping.
It's a classic house with good proportions, IMHO. I wouldn't make any structural changes. Only changes I'd perhaps change are the porch columns for something thicker and new porch railing.

I wouldn't paint the brick. I'd select a gray green color for the siding to help complement the red brick.

I think a new dimensional shingle roof or flat tile roof would look great, new siding, extend the front porch and update railings- and don't forget the fabulous new front door!

Great house and just needs brought to the 21st century as you suggested. First off removing the overscaled planting on the right side of the house will increase the scale of that elevation. . Next,,,,,,remove the shutters everywhere and paint the house a really deep rich neutral color and use a crisp white to trim the house. Lose the turned wooden columns and replace them with a simple column for support. Remove the segemented arch effect at the porch and square up that detail where it intersects with the ceiling. Consider using aircraft cable to form the railing for the front porch and replace the front door with a horizontal rail and glass design. Go to my photos and look at the a project called J, K and R's Residence Renovation and there is a before and after photos of the front and the back that will amaze you by just increased the glass openings and painting most of the details out how it transformed that residence. Paint is a great gift from GOD.

Thanks for all the great feedback and getting the wheels spinning!

The landscaping can be brought into proportion by using retaining walls to make the grade change. For example, a retaining wall that would start at the porch and run to the right to just about the fireplace then step down 6 to 10 inches and continue beyond the end of the house...something like these pics. In turn, you will need a new planting scheme. The shaped shrub look is not doing anything for the style of house. If/when you get to that point, choose shrubs that won't grow above the bottom of the windows and fit into the space so there is no need for pruning.