Leaking Window

A few more pics of your property from a bit further back would help, also is that your neighbours house in the back ground.
 
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Hi, yes that's the neighbouring house in the background. You can see that their bottom tile slopes down properly but mine is sat on a horizontal facia.

I wonder how long it's been leaking. I bet it's made a mess of the cavity insulation. Any other problems this could have caused if its been leaking for years?

Will try to post better pics.
 
Well the most striking thing about your roof and your neighbours roof is the difference in pitch or is that an extension I am looking at.
 
True, the pitch of the roofs are very different. I don't think that's a problem in itself though, all the houses on the street are different designs.

If I look at other photos, the facia and box end are cut to slope down with the roof:


Whereas on mine the bottom row of tiles is horizontal so the water collects underneath and then seaps through and down the inside of the wall:


Does the soffit/facia/guttering/box end etc need redoing? Or is it simply that some of the tiles are letting water through and need replacing?
 
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Your tiles will be letting water in at that pitch when it is raining heavy, the felt is then supposed to take that water into your gutter, but if it is the old type of felt then it will have rotted by now.
 
Try sealing all possible leaks with sealant. I also think that the rain gutter might not be able to heavy rain waters try reinforcing your rain gutter.
 

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