1. Business.com – $345 Million

The $7.5 million spent on purchasing business.com in 1999 lands it on the list of the largest domain name sales in history. But at the time, no one could have imagined that this domain would be worth 47 times more in a period of just 8 years.

The value of business.com spiked after Dow Jones and The New York Times tried to buy the domain in the years following 1999. Finally, in 2007, the domain was sold to RH Donnelly for a whopping $345 million. However, this particular domain name sale did not bring much luck to the buyer. The third-largest print and online Yellow Pages publisher in the US declared bankruptcy just two years after buying the domain.


2. LasVegas.com – $90 Million

This domain was purchased in 2005 by VEGAS.com, LLC which wanted to pair up the two domains to ensure that both search terms directed online traffic to the travel agency from Las Vegas. The massive $90 million sale ensures that this will always be remembered as one of the most expensive website purchases.

The previous holder of the domain, Stephens Media, agreed to a contract that started out with an initial $12 million payment. The remaining sum for this domain sale is payable until 2040.


3. CarInsurance.com – $49.7 Million

QuinStreet, a vertical marketing and online media company from California, made headlines at the end of the last decade with some of the most expensive domain name purchases ever. In the period of just 13 months the company had acquired three huge domain names in the world of insurance, culminating in the purchase of CarInsurance.com on November 8, 2010.

This domain was already a highly profitable consumer site for researching and shopping for auto insurance policies, making it QuinStreet’s crown jewel. With that single purchase, the company solidified its place as a market leader in online insurance at the time when internet shopping was taking off.


4. Insurance.com – $35.6 Million

QuinStreet’s other purchases hold third and fourth spot on the list of top domain name sales.

The second in the trinity of insurance domain names that QuinStreet bought was acquired for $35.6 million in August 2010, along with all the media and the technology assets that Insurance.com already possessed. Similar to CarInsurance.com, this online platform was regarded as valuable because it was a popular destination for comparing insurance rates on cars, health, life, home and renters insurance.


5. VacationRentals.com – $35 Million

Tourism has never been as popular as it is in the modern age of the internet, with countless ways to promote, explore and find the best possible deals to satisfy your traveling needs. Perhaps not surprisingly, one of the all-time top five most expensive domain names for sale had to do with vacation rentals.

Unlike some other top names on this list of domains, VacationRentals.com was purchased solely to prevent a different competitor from snatching it up first. It was 2009, and Brian Sharpies, the CEO of HomeAway, managed to sneak in and purchase the domain after he found out that his rival company Expedia was planning to do so. Before the purchase, VacationRentals.com was already an active site and now represents a marketplace for vacation deals around the globe.


6. PrivateJet.com – $30.1 Million

This is the only domain on the list that is geared almost completely towards the richest of the rich, offering luxury jet charter rentals for global business flights. It seems only fitting then that its purchase in 2012 is considered the highest pure sale of a domain name in history!

The domain PrivateJet.com was purchased for $30.1 million by Nations Luxury Transportation, LLD, an Atlanta-based company that provides travel services. It was bought from an intellectual property holding company Don’t Look Media.com, in the hope that the new website will help attract high-net-worth clients.


7. Voice.com – $30 Million

Voice.com is the most recent domain name sale on the list following what seemed like almost half a decade without earth-shattering acquisitions. It was sold to Block.one, easily topping the list of the most expensive domain names in 2019. What makes it even more of a special entry is the fact that the creator of EOS cryptocurrency bought the domain through a cash transaction facilitated by GoDaddy.

This likely makes Voice.com the single most expensive publicly announced pure domain name purchase of all time. While the previously mentioned heavyweight domains sellers on our list were all worth more money, the fact is that all of these domains were already web businesses before being sold. But Voice.com was not an operational website before being bought and the ultra-premium domain name is sure to help Block.one with its ambition to become Facebook’s biggest competitor yet.


8. Internet.com – $18 Million

We already mentioned how QuinStreet went on a buying frenzy in 2009 with their purchases of the largest insurance-based domains that are firmly in the top five of all time. But that’s not the whole story. The company also bought one of the best domain names, Internet.com, for $18 million in cash. A number of other top domain names were part of the deal, including InternetNews.com, ServerWatch.com, Webopedia.com, Developer.com and others.

The seller was WebMediaBrands, a global provider of news and original information that wanted to sell domain names in order to boost the company’s net balance and focus on its core business ideas.


9. 360.com – $17 Million

This is the only number-based URL on our domain name value list and one of the rare domains of its kind that managed to bring in the big bucks. The sale was made in 2015, when Zhou Hongyi CEO of Qihoo decided to create a new brand that would unify and encompass all of his products and services. The bold move cost $17 million.

The domain itself was sold by the telecommunications giant Vodafone that once created a phone of the same name. And while the number-based domains are becoming less popular in the West, the acquisition was a great move for a company that’s geared mainly towards the Chinese market. Short names and numbers are much more popular in China where numbers have a cultural significance. As such, the high domain name cost is perfectly justified.


10. Insure.com – $16 Million

Who better to end with than QuinStreet – the company that dominates our domain price list with 4 out of 10 top sales of all time in a span of just 13 months. Insure.com was their first purchase of 2009. The sale drove up future domain values after the damaging first year of the Great Recession.

This $16 million sale was worth ten times more than what Insure.com was bought for in the previous purchase in 2001. Insure.com distinguished itself from other big domains like insurance.com by offering more than just a platform to follow new insurance deals. It also provided articles, quotes and news regarding this sector of the industry. Such useful information helped it secure its place as one of the most expensive domains.


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