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Is there a way to transfer the content of my iTunes library from a Windows laptop to a MacBook over our house's network?

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support.apple.com/kb/ht4527 The home sharing option is best if you have an Apple id and store account. – echeola May 24 '14 at 17:16

You could get PuTTY and ssh into your Mac and if that works just do scp -r of the iTunes Media folder. That would get you started. You will have to rebuild your library after that...

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