Beautiful house! It's got a particular style and if you mess with it, it risks being weird.

It's classic as is, although the photos don't really show everything. I would merely clean up what you've got. Replace what needs replacing with pretty much the same style. The windows are kind of perfect for the overall look. (I would replace the stepping stones to the entry with a solid brick walk though.)

Looks more hip than mansard roof . It is very hard to get a feel for the whole house with all tht vegetation . What style of metal roof are you planning and what is your style you want from the changes . I do agree go slowly .

Lovely house. Some background would help. Are you just moving in? Fixing up for selling? Have you grown all the landscaping for years yourself?

I would start with pruning the shrubs so that nothing is close than a foot from the house walls. Air needs to circulate, as you can see from the bottom photo. Then hire a landscape architect for a two-hour walkaround and consultation. Ask about transplanting small trees and shrubs if they are too close to the house.

Re-roofing can damage landscape plants when things fall where they weren't supposed to. Nails end up scattered on the ground. Talk to your roofer about covering valuable plants with plywood shields and tarps. Don't plant anything new until the new roof is finished.

It's not a mansard roof, it's a hip roof. If the roof is failing, then, of course, you need to replace it. Otherwise, it's fine. You have lovely, lush landscaping. I'd keep it.

Yes, I would replace the fake rock with stucco also.

Reason for roof replacement? Leaking? Because I like what you have. Just needs cleaning.

Thank you all for your in-put! A few answers to your questions...we are looking to replace roof (with metal) and yes, the landscaping is way overgrown...I am considering starting from scratch re landcaping. The House is mixed roofs with mansard front (elevation). While updating windows and roof, and landscaping, we would update the whole elevation from the street.....I know its a lot... It has been difficult for me to peice it all together while being consistent with the architecture of the house. Whew...so any help ideas are greatly appreciated.

I forgot the driveway..we plan to make the island in-front smaller and make the landscaping cleaner and lower maintenance...perhaps french or hollywood regency friendly...

You've got a lot of great, mature plantings, mostly in pairs or trios. I see a couple of banana trees near the garage, 2 or 3 palms in the center of the house, and another few palms to the right. You have a rather straggly shrub (Hibiscus?) and a very lush palm-like shrub. Rather than pulling it all out, I'd ID the stuff you have and remove some of it. I'd cut back the hibiscus and the palm-leaved shrub. I'd put the focus on the front door., for example, removing 2 of the 3 palms next to it.

You should chop down one tree of the pairs and threes at a time, then leave it for a while.

If the banana-like thing is all one plant, you can dig up part of it, leaving the rest.

The fern is too close to the house. I'd move it elsewhere. You have a lot of gravel that could use some greenery.

If you can save the concrete tile roof it can be cleaned and restained in a new color provided you don't have any leaks & find a good roofer which is often the issue down here. Insurance companies are loathed to insure any homes with roofing that is what they consider 'old'. That could be as few as 15 years in FL.

Here are some ideas:

@BeverlyFLADeziner, do you have a source for the metal roof that looks like tile? I can google it, but thought it was beautiful. The front of this house looks very similar to my mom’s garden home in Phoenix, but the plants are definitely more tropical and not desert.

I really like the lush landscape. Hding the house is a plus to my eye. Obviously I don't know your conditions but I think it would be a shame to remove those wonderful mature plantings. I'd prefer to edit and steer rather than lose those healthy, flourishing plants. I'm not sure why the fern is considered to be too close to the house. It's only a fern, so shouldn't be damaging the structure, unless it's very flimsy, and it is growing lustily under an overhang where not much else would succeed.