The Most Expensive Domain Names Ever Sold

A little over 20 years ago, domain worth and the value of a website name were little more than an afterthought. But on August 9, 1995, everything changed, and the Internet craze began.

That was when the small internet startup Netscape went public. By the end of the first day of trading, the company was valued at nearly $3 billion. The ensuing gold rush is now known as the dot-com bubble.

Over two decades later, domain names are still considered a wise investment - even after all the ‘good ones’ were taken.

That’s why we put together a list of the most expensive domains to help you understand what makes a good domain name, how they became so valuable and other key characteristics.

The Essentials of a Great Domain

Before we talk about the biggest domain name sales ever, it's important to understand the essentials that have so far impacted the sale numbers the most.

There is only one king, and his name is .com

Many domain name extensions over the years sought to dethrone the .com domain. But .com has endured the ages.

So what is .com and what makes it so popular? It is the most dominant of all Top Level Domains and is being used in about 47% of all websites.

With such power and reach it should always be considered a priority when registering a domain name.

While other TLDs like .net and .org are well-known too, .com is simply the most recognizable globally.

Keeping it short and simple

When it comes to domain names, shorter was almost always better.

The most prized domains are usually ones with three to four letters, excluding the TLD. But the general rule is that domain names with up to 10 characters can also be worth it.

You should also always keep the name simple. In other words, avoid hyphens, underscores or any sort of punctuation.

Although numbers should be avoided, there are rare cases like 9gag.com that have proven to be successful.

Memorable and brandable is successful

So, you managed to snatch up a three or four word domain, but it is spelled something like “kgmp.com”. If you access the website, you find an empty domain waiting to be sold.

This is explained by the internet craze of the late 90s when domain sales were going through the roof.

At the time, many were certain that any letter combination making up a three to four-word name would make them rich. They were very, very wrong.

Truly valuable domain names are not only in short supply, they are also memorable, relatable and have branding potential.

But from time to time, even some of these seemingly meaningless random combinations will strike gold.

This is made possible by the fact that large parts of the world are still developing and certain local companies can match your weird domain name with their own brand, suddenly making the previously useless domain worth something.

Since these sorts of occurrences are rare, it’s much better to invest into domains that actually have a vowel or two.

Descriptive names can work, too

This is probably the biggest exception when it comes to the shorter is better rule.

Descriptive names that are much longer but serve to fill a popular search term and consumer need can be incredibly valuable.

For instance, a domain like “carinsurance.com” is one of the most most valuable domain names ever, even though it contains 12 letters.

Its incredible value proves that certain longer word combinations are still very profitable and will continue to be in the future.

With enough foresight and knowledge about emerging trends and technologies, it will always be possible to make money and sell a domain name with a search term which is about to become popular among the public.

Being aware of copyright and trademarked terms

One thing that everyone should do before purchasing any kind of domain name is to check if they are infringing on any existing trademarks.

You should never enter into an investment without searching up companies that might have trademarked certain names.

Top 10 Domain Sales of All Time

These are the largest domain name sales which as of right now stand ahead of everything else:

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.

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.

CarInsurance.com - $49.7 Million

QuinStreet, a vertical marketing and online media company from California, made headlines at the end of the last decade.

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.

Insurance.com - $35.6 Million

QuinStreet’s other purchases hold third and fourth spot on the list.

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 policies.

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.

Unlike some other top names on this list, 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.

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.

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.

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.

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 Internet.com, for $18 million in cash. A number of other big 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.

360.com - $17 Million

This is the only number-based URL on our 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.

Insure.com - $16 Million

Who better to end with than QuinStreet - the company that dominates our 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.

The Future of Domain Names

Our list of multi-million dollar domain sales has one common denominator - the sheer dominance of the .com TLD.

Dot-com is synonymous with the internet and the power of this TLD appears to be growing, which is why we labeled it as a key factor to owning a successful domain. But the complete reliance on the .com TLD pushed domain name prices through the roof.

To try and curb the world’s reliance on .com, the Internet Corporation for Assigned Names and Numbers (ICANN) is trying a different approach by pushing to ease the rules of TLD registrations.

This would allow for almost any word to be considered a valid choice for a domain extension, opening the door to thousands of new TLDs.

Companies could register domains like “renta.car” or “buya.house”, and if successful, these creative solutions have the potential to change our understanding of what it takes to sell a domain name for a record price.

Bottom Line

Web domains have grown in value and importance along with the Internet, becoming a powerful marketing and branding tool for companies thriving in the information age.

These simple, single lines of text have the potential to propel local brands to internationally recognized giants.

In the past two decades, domain names have been the bedrock of the Internet with the .com firmly planted as the dominant force. But times are changing, and the sphere of domain names is ripe for a revolution.

So, will history’s most powerful TLD retain its dominance, or will the future list look completely different?