Hire a crew with chain saws and take out all the undergrowth, but keep the trees (palms). Then reassess because this has gotten so overgrown it is a do over. Some might tell your to hire someone to decide what to keep but I don’t think that is an option at this point, maybe 10 years ago, but not now. Once we can see the house, repost your photos for further ideas.

I garden 2.75 arces of land, cross fit train 3 times a week and have titananium rods and plates in my spine from a spinal cord injury. I can do military push ups, row, jump on boxes and go for about six hours in my yard with a 24 year old college student who cannot keep up with me. I am 56. Yes I would hire a crew to take out the major stuff. See what they can clear in a day and then you can tackle the rest. Unless you and your hubby are extremely fit people and have landscaping experience you have no business tackling it. This is a major job. It’s so major that even I wouldn’t tackle it myself. I think you are underestimating how big of a job this is going to be. Besides you will need to have the debris hauled off. In Florida I am sure you can find a crew to work for cash. One other comment, you have fire ants and other critters that can quickly come out to bite in all the overgrowth. Alligators included. Is this really worth getting hurt over? No. Save your energy for the installation and other work that I am sure will need to be done.

Great piece of property. Suggest you consider what you like most about the area around the house, things you enjoy doing outside, and jot down a few of those thoughts. Once you have a sense of what you would like to do outside your property, develop an outline. This outline will serve to guide your next steps in the process of landscaping and hardscaping.

It seems to me that the previous owners went to great lengths to hide the house. Yes I'd get the removal crew and leave the palms. Since you can't remove the arched wall play up the arches a planter in front of each pillar with something tall them. It seems to me your house must be Spanish architecture and you can find lots of photos on line with Spanish arches and how they are dressed with plants

some ideas

Thank you...if you need help down the road, just let me know.

Whether you can do it your self depends on your gardening knowledge. Do you know what's there, can you prune? I would identify what's there, find out how it could look if properly pruned, and THEN clear out everything else. No sense throwing out the baby with the bathwater. Mulch can cover the ground in between then until you have more of a plan in mind.

Ana474, I see that you and I share some landscaping sensibilities. Even if cleaned up, I do not find the current design appealing. The property is roomy but two islands oddly dwarf the entrance to the house. The fact that one island is a bit high makes it seem to loom over the arched entrance. I see no design reason for those beds to exist. I would create extra beds only after I had run out of room at the house itself.

The foundation bed to the left of the arch is deep but has been designed poorly. It could be made beautiful. On the overhead map I see another overgrown area off the right side corner of the house. I think that area needs attention too.

I am not pleased with the Ring Around the Rosie paving either. It offers a path to nowhere and is just perplexing. I believe the paving should lead to the entrance and if you want interesting paths on the property they would be better somewhere else.

If I had purchased this home I would remove both the front island beds and never look back. The trees you find attractive can stay and the area may need to be somewhat elevated but could be much lower.

I would replace with lawn leaving a smallish bed at the base of the tree.

When someone calls their house a fixer upper I think of it as a long time project. If you are not in a rush I think you can do a great deal of the work on your own. You did not say if you have experience with garden clean up. I've done a bit of it for friends and neighbors over the years. It is tiresome and tedious and dirty but I don't find it difficult at all. A good thing about doing the work yourself is that you can familiarize yourself with what plants you have, discover their names and then consider if you want to have a goal or removing them some day. There is a Name That Plant forum that you may find useful.

The one area I might hire out for is the two islands that I would demo. Someone with a Bobcat could smooth them out quickly. Hand dig and remove plants you want to keep in advance. If you want to pile the soil somewhere else for a new island I would consider the view from inside the house.

Good luck and please post update photos.

Ana, one of the posters was correct about at least walking the grounds and marking what you want removed and what you want to keep. Green ribbons & red ribbons work. That will at least familiarize yourself with the plants. The reason I cautioned you is that I had a half a pine tree fall over on my driveway. I got out my chain saw one morning and tried to tackle it. OMG there is no way I by myself could do it. And my mess was a 1/4th of what you have. I also realized that if you are not use to working with chain saws etc. major landscaping clean up is not the place to learn. That said, mark off one island and try to tackle it if you want to see the effort needed. But your landscape reminds me of trying to recoup the Amazon jungle - you know where you machete the path and turn around and its already overgrown. LOL

And I would love to see the house once the Amazon is cleared. LOL

Emmarene is right to point out that you should have a general plan in mind for the front, so as to not waste time saving plants that are going in the spot of the new driveway, path, etc. Plan first, then hardscape, then worry about plants. Clean it up a bit if you need to wait on time for planning and money for hardscaping. Who knows what your priorities will be inside the house too. You can also hire the cleanup done, but the key is to know what you have and want to save.