Homes in the lower Southern Highlands are being impacted by a rapidly spreading spot fire that jumped from the main Currowan fire burning near Kangaroo Valley.
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Fire is currently burning on multiple streets in Wingello and Bundanoon, with reports homes have already been lost.
There are also reports of ember attack on Wingello Public School and the rail line is closed.
There have been several triple zero calls for grass fires and blazes are crowning in trees.
Dozens of crews are being sent to the townships, while residents are being evacuated.
Just hours earlier, Southern Highlands RFS had posted a message on Facebook advising residents it was "unlikely" the Currowan fire would reach the Highlands tonight.
An update posted about 11 o'clock said it was "too late" for residents in Tallong, Werai, Exeter, Manchester Square, Avoca, Fitzroy Falls, Barrengary to leave their properties, with fire approaching rapidly.
The Illawarra Highway is closed between the Hume Highway and Moss Vale. The Hume Highway may also be closed at short notice.
