Audioengine 5+ multimedia speakers

An CNET Editors' Choice winner, Audioengine's 5+ powered speakers deliver big sound and audiophile-grade performance. Add any audio source (PC, iPod, phone) and you're good to go.
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Bose QuietComfort 15 headphones

Yes, they're on the pricey side at $299, but we haven't met a dad who wouldn't mind getting a pair of these headphones as a gift.
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Sonos Play:5

You won't be able to get a multiroom Sonos setup for $500, but you get Dad a Sonos starter set with the Sonos Play:5, which comes in white and black (or step down to the Play:3, which retails for $100 less).
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Bose SoundLink Bluetooth Mobile Speaker II

The Bose SoundLink Bluetooth Mobile Speaker II delivers excellent performance for a portable Bluetooth speaker. It comes in a standard ($299.95) and LX version ($349.99).
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Slingbox 500

For the Dad who's a sports fan and wants to catch his teams on the road, you can't beat the Slingbox 500, which allows you stream your home cable or satellite feed to mobile devices and computers.
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Panasonic Lumix DMC-FZ200

The Panasonic Lumix DMC-FZ200, our current top choice for megazoom cameras, can be had for just less than $500.
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Sennheiser Momentum headphones

The natural, pure-sounding Sennheiser Momentum headphones will appeal to audiophile dads.
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MyCharge Peak 6000 Rechargeable Power Bank

It may not have a Lightning connector, but the MyCharge Peak 6000 charges just about any other kind of mobile device (except laptops).
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