20. Candy.com, $3 Million

Year: 2009
Buyer: G&J Holdings

Purchased from the "Domain King," Rick Schwartz, Candy.com was let go for a cool 3 million to a company that planned to turn the domain into a the premier online destination for-get this-candy. The site would boast cheap, quick shipping, and competitive pricing. Before the sale of Candy.com, Schwartz made a killing when he sold ireport.com to CNN.

19. Vodka.com, $3 Million

Year: 2006
Buyer: Roustam Tariko

If you live outside of Russia, you probably have no idea who Roustam Tariko is. But if you enjoy good vodka you've undoubtedly had his product. Tariko is the billionaire owner of Russian Standard Co., the company that owns and produces the Russian Standard brand of vodka. Instead of turning vodka.com into a digital billboard for his brands, Tariko opted to create a vodka information site that would aim to educate people about the joys of vodka. How nice.

18. AltaVista.com, $3.25 Million

Year: 1998
Buyer: Compaq Computer Corporation

Remember AltaVista? If you've been using the Internet for more than 10 years, you should. Back in the '90s, before Google came through and crushed the game, AV was one of the 'Net's premier search engines. When Digital Equipment Corporate, the company that owned and operated AltaVista, was sold to Compaq, it was decided that AV would be an online portal. There was only one problem: Compaq didn't own the domain name. $3.25 Million later, that was all worked out.

17. Shop.com, $3.5 Million

Year: N/A
Buyer: Lee Lorenzen

Looking to create an online destination where people could easily browse through a number of catalogs, Lee Lorenzen founded a site called Catalog City. From there the vision grew to include products from web-only shops, popular department stores, and speciality stores. Backed by a great purchasing technology called OneCart, all CatalogCity was missing was a new name: It came in the form of Shop.com which was picked up for a little over $3 million.

16. YP.com, $3.85 Million

Year: 2008
Buyer: AT&T/Yellow Pages

You may not have noticed it, but Yellow Pages, the formally venerable listings company went through a brand transformation a few years ago. Looking to breathe new life into its property, AT&T re-branded YellowPages as YP. To go along with its new name, Ma Bell scooped up the accompanying domain name from Live Deal.

15. FreePorn.com, $4 Million

Year: 2008
Buyer: N/A

With the proliferation of free porn sites, you could imagine how sought after "FreePorn.com" would be. We can only imagine how many dudes Google the words "Free Porn" each day. That said, when the domain hit the auction block it was only estimated to sell for $3 million. Unsurprisingly it sold for a million more.

14. Clothes.com, $4.9 Million

Year: 2008
Buyer: Zappos.com

When Amazon acquired Zappos.com in 2009, it came out in an SEC briefing that along with the popular shoe and clothing site, Amazon also inherited Clothes.com. Turns out Zappos purchased it a year before it was sold to Amazon to funnel shoppers directly to its clothing section.

13. SEO.com, $5 Million

Year: 2007
Buyer: WashingtonVC

Michael Mann, founder of venture capital firm WashingtonVC, knows a thing or five about making money on the Internet. A few years ago he sold his company, BuyDomains, for over $65 million, then began to fund a series of SEO companies. It makes sense, then, that he would fork over major paper to get SEO.com.

12. AsSeenOnTV.com, $5.1 Million

Year: 2000
Buyer: LA Group, Inc.

According to some analyst, the American informercial market is a $150 billion industry. That's what propelled LA Group to purchase the domain AsSeenOnTV.com. As one of the most recognizable brands, AsSeenOnTV bought with the plan of turning it into the one-stop shop for all things you, well, see on TV.

11.Toys.com, $5.1 Million

Year: 2009
Buyer: ToysRUs

As America's premier toy store, ToysRUs wanted a digital hub for its three retail properties: ToysRUs, eToys.com, and FAO Shwarz. And what better place to showcase your toy-related brands than Toys.com? To make sure it acquired the domain, ToysRUs went through a vigorous auction with National A1 Advertising.

10. Casino.com, $5.5 Million

Year: 2007
Buyer: Mansion Limited of GIbraltar

Not much is know about the sale of Casino.com. All we know is that it's owned by a company headquartered in Gibraltar.

9. Slots.com, $5.5 Million

Year: 2010
Buyer: Calvin Ayre

We do, however, know a lot about the sale of Slots.com. We'll let the buyer tell you why he spent such a crazy amount on something that's not sure to bring a return on his investment:

"Even at $5.5m, I'm convinced the Slots.com price was a steal. It's the strongest gaming-related domain out there and just a very cool domain to turn into a global brand. In that regard, it certainly doesn't hurt that we're getting a lot of help in publicizing our brand from the sex-crazed media. The press we garnered from the initial Slots.com purchase was massive, but now every single press mention of the Sex.com sale has also mentioned Slots.com by way of comparison. There have been over 100 press mentions across the globe in the past week alone. When you look at the costs involved in fostering a brand identity on a truly global basis, the free publicity has already made up what we paid for the Slots.com domain. History will bear me out – this is one of the best deals I have ever made."

8. Israel.com, $5.88 Million

Year: 2008
Buyer: N/A

The buyer of Israel.com opted to remain anonymous, but when the sale went down, it was the seller who became an overnight celebrity. The domain was owned by a then 46-year-old Jewish American named Joel Noel Friedman. A forward-thinking Friedman picked up the domain back in 1994 so that no one would misuse the name. He only decided to sell it in tribute of Israel's 60th anniversary, and didn't expect to make such a large profit

7. Beer.com, $7 Million

Year: 1999
Buyer: Interbrew

Want to talk about making your money work for you? The URL beer.com was purchased in 1998 by Andrew Miller and Michael "Zappy" Zapolin for $80,000. The site was pitched as a destination for people to come and rate their favorite and not-so-favorite brews. A year later, however, a company called Interbrew stepped in and bought the domain for $7 million. There are some conflicting reports that say Interweb didn't pay the $7 million in cash, but rather gave them $7 million in stock, which was later claimed for only $2 million. Still, $80,000 to $2 million isn't a bad outcome.

6. Diamond.com, $7.5 Million

Year: 2006
Buyer: Ice.com

We think Ice.com is one of the best domain names for a jewelry retailer, but what do we know? Apparently the European company wanted a more traditional name for its website and opted to buy Diamond.com from the ailing Odimo, Inc. It even decided to purchase the rest of Odimo's stock and inventory along with the domain name.

5. Business.com, $7.5 Million

Year: 1999
Buyer: Jake Winebaum and Sky Daton

Eight years before R.H. Donnelley purchased the entire company outright for $345 million to compete with SuperPages and YellowPages, Business.com was owned by two friends who purchased the domain name to create a B2B site. Many laughed at the purchase, especially after the Internet bubble popped, but the two got the last laugh when they sold for 46 times what they originally paid.

4. P.orn.com, $9.5 Million

Year: 2007
Buyer: MXN Limited

We don't know the exact figures, but we can imagine the number of daily visitors to Porn.com is much higher than even we can estimate. MXN wouldn't release exact numbers when it purchased the adult industry's top domain; it only said that it paid more than $9 million. A writer for Moniker.com, a domain name service, did a little more research and discovered it was sold for a minimum of $9.5 million.

3. Fund.com, $9.99 Million

Year: 2011
Buyer: Eastern Services Group

From the moment the sale of Fund.com was announced it was mired in controversy. First, it was actually sold for $9,999,950. Secondly, it was sold to a Nevada-based company called Eastern Services Group which worked as a tax advisor to casinos and which recently went public. It was then revealed that the company was in business with a number of shady parties like Westmore Capital which was closed down by the SEC for running a $53 million Ponzi scheme. Then came the rafter of acquisitions that did nothing to help Fund.com's bottom line. By September of this year Fund.com lost 99% of its revenue.

2. Sex.com, $13 Million

Year: 2006
Buyer: Escom LLC

Sex.com went through a lot before breaking into the Guiness Book of World Records for High Price Paid for a Domain. It started in 1994 when entrepreneur Gary Kremen (the man behind Match.com) registered Sex.com with Network Solutions. A year later, ownership of the domain was transferred to a man named Stephen M. Cohen. Why? Mr. Cohen tricked Network Solutions. Using forged letters and fax faxes, Cohen was able to convince the domain company to grant him ownership.

From there, Cohen set up a site filled with advertising that was registered 25 million hits a day. At one point, he was making up to $500,000 a month from the site. Kremen caught on and took Cohen to court for what turned into a five-year legal battle. In the end, Cohen was ordered to give up the domain and pay $40 million to Kremen for lost earnings. But before he could pay, Cohen fled to Mexico and was detained in Tijuana in 2005.

1. Insure.com, $16 Million

Year: 2009
Buyer: Quin Street

When Sex.com sold for $13 million it entered the Guiness Book of World Records as the most expensive URL in history. Three years later, Insure.com sold its corporate name and related domain name to Quin Street-who also bought Internet.com months earlier-for $16 million, making it the most expensive domain name ever sold.

That's one of the craze for a common name domain. I guess they will be regretting by now for purchasing those domain for such amount. shop.com? Who has heard of that? While ebay.com and amazon.com ar household name. Google.com. How many millions of dollar did the owners buy it? Nothing was paid. Today, u cant do anything meaningful in a day without using google. facebook.com. How much did Mark buy it? Today, all the 20 domain names put together cannot equal it. israel.com shouldnt have been bought at all. The nation of Israel could hav claimed it if they wanted. The point is that domain name doesnt matter a lot these days. U can choose a name that even sounds abstract and turn it to a brand. hp.com is just an abbreviation of names. dell is someone's name. So to me and to those that understand branding, having a name like dati.ng, hosti.ng, or wel.com will not make u prominent and it wil not bring conversion to u. Am yet to know that there is a website called sex.com, clothes.com and the likes.

Thanks for posting this list. I thoroughly enjoyed it.
It reminded me of a day I considered registering what I though was a killer (.me) domain for 5k.

I delayed for over 2weeks. When I finaly decided to register it. It has been bought and offered for resale at $5000 !
I learnt my lesson, when you make a mistake, dont blame yourself.
Blame GoDaddy free domain search.