Dad's Chimney is leaking

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This Home is in SW Florida. The fireplace below never burns wood anymore, not for 20+ years, only propane, and it rarely gets used.

I've no experience with roofing, or chimneys.

A damp spot further developed on the interior ceiling after a tropical storm this year, just downhill from the chimney.

He had some handyman type guy here a few months back, who seemingly just sprayed some white flexseal around the exterior, overcharged him, and left.

During a rain yesterday I climbed into attic and sure enough, as expected there is drips running down the pipe.
Today, I climbed onto the tile roof and got some photos.

Looks like a whole bunch of bad design/halfashery by whomever built the house, or last did the roof.

With no wind, no rain gets inside, but with any wind, it easily does. high wind and heavy rain and it must be quite damp up there.

My dad did not want me going up on the tile roof, and does not want me to try and fix this, but I don't want him calling some guy who is going to rip him off, again.

I'm a capable handyman type but no experience with florida style construction and no Chimney experience.

I was thinking removal of the 8 rusted bolts, shortening the legs about 2 inches with my angle grinder and cut off wheel, drilling 8 new holes and reattaching with some stainless.

Any Advice/ recommendations?

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You can "spot splash" with a hose small areas at a time and see where the water is coming in. It does look like the sealant is not in good shape and needs to be replaced. Otherwise, your best bet would be to have a qualified roofer take a look at it. Not everyone is a con artist and do honest roofing work.
 
Not a expert either, but I question why the big pipe has a gap around it? The pic showing inside to top shows the gap I'm talking about. The actual chimney pipe is smaller and inside the big pipe......right? I would get a collar to fit around the big pipe gap and close off the gap. That gap doesn't vent the fireplace. That might fix the problem as the smaller pipe opening is further up into that "box vent thing". Good Luck !!!
 
Really happy with Galvanston Daniels, G&D Roofing, 239 281 4070. Based in Lee County.
Edit, he is more of "roofing" guy, you may need more of a sheet-metal guy.
 
The whole setup looks wrong. That cage on top either needs to go or a transition pipe needs to be added. Whatever needs to be done, I would hire a professional. The rectangular cutout in the roof suggests that a traditional style chimney was intended.
 
That is a complete Charlie Foxtrot. That cage setup is stopping the direct rain from coming in but you are getting splash off of the roof and that cage going down that gap that shouldn’t be there to begin with.

It’s missing a collar and flashing. I’m surprised you haven’t had issues with wasps etc.

Definitely have a professional do that.
 
That's probably triple wall pipe, so be prepared if you try to do anything yourself. The problem is obvious, that "sideways rain" blows right into the gap, and the collar should be higher. Don't block any of that off, as it's intended to have an air gap to prevent heat transfer to any wood. Yes, those are the right parts, but put together about as incorrectly as possible.
 
In the one photo looking up in post #1, one can see water drips running on the outside of the pipe. Rain with an horizontal element getting inside.

I got some angled flashing and attached it to the 4 sides.

Now the rain would have to be travelling perfectly horizontal, and defy gravity to get inside.

The surface area for attic venting is a now smaller, but I was able to feel ample hot air exiting around the space left for the attic to vent.

Dad's happy.

Cost of the flashing, $7.49
 

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Nice fix.

100% of the houses in Florida do NOT need a fireplace.... especially SW FL.
 
That is a complete Charlie Foxtrot. That cage setup is stopping the direct rain from coming in but you are getting splash off of the roof and that cage going down that gap that shouldn’t be there to begin with.

It’s missing a collar and flashing. I’m surprised you haven’t had issues with wasps etc.

Definitely have a professional do that.
Haven’t heard that Charlie Foxtrot remark since my Navy days. Gave me a laugh.
 
I'd go one step further by bending your additional flashing down at a 45° angle. That should fix it then for sure!!! Good idea you had !!!!!!!!
 
I'm wondering if warm air is rising up and when it gets to the cooler pipe, forms condensation, which runs back down as water. Should not be such a gap.
 
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