Really like Jen's rendering. I like that the pillars are just a bit darker than the siding, so they don't stand out, but it isn't all the same either. I agree, landscaping is your friend here. Some tall plantings in front of the pillars will minimize them a bit and the railing helps to lighten the effect. If you're feeling like something a bit different, I think colorful trim would look nice with the off-white color scheme. Maybe blue.

Well done Jen.

On second thought, Gillian you can even do without the little path, just landscape the all front!

Willing to bet there was a railing there originally and it might still be under that vinyl.

Nice rendering. Great ideas!

You have a pretty cute arts and crafts bungalow with all of its details flattened with paint and vinyl. Remove the vinyl. Pay way too much to have the paint taken off the brick and stone columns (it's going to be expensive but you only have to do it once, or diy it with gallons of soy gel). Then pick a paint scheme based on the brick and stone colors.

Thanks for all the great tips! In the long run, I think we want to remove the siding (but we are getting sticker shock over how expensive it is, plus repairing the stucco underneath). I'm thinking about taking paint off the pillar around the side (near the front door) to get a peak at what might be underneath, and then deciding how to move foward. Jen - I love your rendering and I think that would give us a great upgrade!! Love the idea of taking out the path as well. Will definitely post some pictures once we have made some progress

Good luck Gillian!

Maybe have a look around your town for houses of the same vintage as yours, with some unpainted stone features, pillars or other. Back in the days people used local materials and you will get a good idea of what might be under the paint by looking at those other houses.

Too bad about the sliding, but at least it's really not that bad!

In what way does the stucco need repaired?

I have heard there is something called soda blasting that will remove paint from your stone work.

When you get to that point, and if you are at all handy, you should be able to remove the vinyl siding yourself. Just don't do it until you are ready to have the stucco repaired.

emmarene - not sure what the vinyl siding is hiding in terms of cracks, holes etc. So those would need to be patched and the texture matched or redone. I've also seen a few youtube videos with 250 degree pressure washing to remove paint from brick.

Often people covered good stucco or wood siding simply because they liked the idea of never painting again. There may be nothing wrong with your stucco. It will need a bit of repair because of the means used to attach the siding. Vinyl is never an upgrade of real stucco, which your house has.

If you are not too aged and somewhat physically capable you can remove that vinyl yourself. Do you possess a claw hammer?

I would kind of love to do it myself! I don't have a claw hammer but I could definitely get one.

Fingers crossed there's nothing wrong with your stucco. Unless there was water damage and mold, stucco is pretty darn tough. This may not be as expensive as you think.

Let's hope it's not!

Hammer and a 12 inch flat pry bar, along with some wood scraps so you don't press directly against the stucco with your hammer and pry bar. Gloves and eye protection too please. You'll be very good at removing vinyl siding by the time you're done...

It would be a huge improvement to a nice looking home.