Probably Total War Master Edition, I've given that away at least twice and paid around $12 for each copy ($120 valued). The most expensive games I've bought in real cost for giveaways are probably the 2 copies of Arkham Knight, Witcher 3 and Fallout 4, but I typically hunt for deals when possible.
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Batman: Arkham Knight Premium Edition So far I've gifted three copies of it paid $28 each
Also gifted a copy of Grand Theft Auto V - paid $60 for it.
I try to avoid gifting Bundled Games at all cost.
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If i tell you, you kill me ;)
Dawn of War Franchise Pack - 140bucks worth
paid around 11 bucks =)
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there were some games (like Alien Isolation, Evil Within...) i paid 20-25$ for.
EDIT: oh, misunderstood the thread a little. ^^ i guess the most expensive item i gave away was serious sam complete pack. i think it was 100 points, and i paid 17€ each (5 copies, i believe).
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Back before The Darkness II wasn't bundled, I gave that away and payed about 5 euros I think. I love that game so much I had to make a giveaway for it haha. Sadly the winner didn't even play it :(
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BIT TRIP COLLECTION - 49,99 now, 59,99 before , and i actually traded it for 1 TF2 key :3
And
Transformers™: Fall of Cybertron™ - 54,99, which i traded for 2 TF2 keys.
The amount of amazing deals we had before region locking, were fucking awesome.
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Tomb Rider, it was still in ~30 bucks or so like a year ago, i got 2 copies for 5$, one for me and 1 to GA.
Also, rome total war 2, i got it in 5$ bucks too when it was full price (60) before the game had any discount, i really wanted to give a copy, but i just could get my hands on the last key the guy had, had to use it for me, love TW.
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I believe it was Skyrim, Legendary Edition, at full price. There have been quite a few games I've gifted at full price (not always by choice), so I could be wrong. I think, however, that I am safe in saying that the most I've ever spent on a gift is $70.
The most I've ever spend on a single game (in one go) is $250, and that was Lord of the Rings Online, Founder's Edition (with a lifetime sub).
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The Witcher 3. Prepurchased it from the Steam store.
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Deus Ex Collection, back when it was very new. Paid a TF2 unusual hat for it (well paid that for Max Payne 3, which was a scam as it was Russia only). Never played the original deus ex, even though I love the series, but I thought that my horrible experience should make others happy, so I gave it away. :)
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I'm not sure... But probably Retro City Rampage... Pretty much all the others were bundle games... I cannot remember the price... :/
I'm pretty cheap... sorry xD
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EA Racing Pack ($70) - cost me nothing. Was giving it away to promote a friend's racing game group and he provided the game for me. I paid for some other giveaways to promote his group out of my own pocket to help him out but not that one.
Most I've paid for a single giveaway game is somewhere in $15-20 region which I've done a few times.
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For the sake of this discussion, let's just limit answers to non-bundled games only. Mine was The Daedalic Comedy Selection (45P) in which I actually paid $8.99 for it.
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