Whether you self-host a website from your NAS or host it in the cloud, you'll still need a snappy domain name to use for it. That's an easy thing to say but a tricky thing in practice, because most of the short or one-word URLs are owned by other people. Even if these domains are just parked, they could be worth a tidy sum, as short URLs are easy for people to remember, and they can make or break your site's success. So, if you're building your company's brand and want one of these parked domains, the only way to get them is to fork over almost unthinkable wads of cash to the existing owner.

Some of these URLs changed hands for hundreds of millions of dollars, with one site being close to a billion dollars. Note that this is just the domain name and not any of the infrastructure or website contents in most cases. The market for URLs is only going to get hotter, as the notable site names were all registered years ago. Let's talk about why, even when these site names cost a lot of money, the tight branding they bring is priceless to the company that owns them.

7 Chat.com

Recently changed hands when OpenAI paid upwards of $15.5 million for it

OpenAI's ChatGPT recently got a new home, or more precisely, a new URL pointing to its existing home, because ChatGPT's own URL isn't going away. But, now chat.com also points to the chatty AI bot, and all it cost was upwards of $15.5 million in OpenAI shares. The previous owner was Dharmesh Shah, founder and CTO of HubSpot, who confirmed on X that he received more than the $15.5 million the URL cost him. It's a perfect URL for ChatGPT's creators to hold, even if it has the spicy baggage of being a video chat site from the early days of the internet.

6 The Million Dollar Homepage

Okay, this one has never changed hands, but it's too cool not to include

While every other website on this list changed hands for millions of dollars, The Million Dollar Homepage is slightly different. It's the brainchild of a (then) about-to-be student from the U.K. who was worried about debt, namely the amount of student loans he would owe after his Business Management degree. The enterprising youngster came up with a plan–make a website with a snappy URL, and auction off space on that homepage for anyone who was willing to pay. The Million Dollar Homepage was born, consisting of one million whitespace pixels, each priced at one U.S. dollar.

The idea went viral, so much so that the Alexa ranking of web traffic had it at number 127 in the world, and during the auction for the last 1,000 pixels, was DDoS'ed off the internet for a week. The URL lived up to its name, making $1,037,100 for the creator, Alex Tew. Most of the site was sold in 10 x 10 pixel "blocks" and the purchaser could put their logo on it and have it hyperlink to their own site. It's still online nearly 20 years later, but many of the links have succumbed to link rot and no longer go to functioning sites. Also, fair warning: the types of companies that bought space range from advertisers to scammier sites and some smut peddlers, side-by-side with banners for legit institutions like The Times.

5 AI.com

OpenAI again, splashing out $11 million dollars for this eponymous URL

AI companies have been spending money like it's going out of fashion to build new AI-powered features into our operating systems and other products. So it's perhaps unsurprising that OpenAI spent $11 million dollars on a URL (via DomainInvesting.com) named after the service they've staked their company's future on. AI.com might not be the site where OpenAI hosts its products, but it's too valuable to let a competitor have access to it, and they rightly grabbed the domain rights when they could.

4 Cars.com

An eye-watering $872 million, even if it was part of a package deal

When your business is selling cars through a website, what URL do you think will dominate the top of the search rankings? Cars.com changed hands to its current owners in 2015 (via DomainGang) for the cost of nearly a third of the $2.5 billion dollars the online car showroom was valued at. That's just over $872 million dollars, so you don't have to do the math. That's by far the most expensive URL purchase that we know of, but we only know about it because, as a publicly traded company, Cars.com has to publish its yearly financials. If it was a private company, it wouldn't be bound by that, so it's possible that some other one-word URLs might have changed hands for a higher amount.

3 business.com

Last sold in 2007 for $350 million dollars

There are two main themes that run through these purchases, and this is a standout example of both. Short, one-word URLs that align with your core business are valuable, possibly many multiples of the yearly income the site hosted on it brings in. The other is that the closer to the top of the search results the URL is, the more it can be leveraged for future earnings. Business.com underwent a fierce bidding war in 2007 (via TechCrunch) with the New York Times, Dow Jones, and the eventual winner, RH Donnelley, all involved. RH Donnelley's core business is several white and yellow pages directories across the country, so purchasing business.com, which was a business search site, made perfect sense, and it's probably paid for itself several times over by now.

2 LasVegas.com

Sold for $90 million to the Las Vegas Convention and Visitors Authority in 2005

Ahh, Las Vegas. The lights, the casinos, the 24/7 buffets, and a veritable army of Elvis impersonators. It's also home to a very expensive website currently owned by the Las Vegas Convention and Visitors Authority, essentially the tourist board but significantly more wealthy than your local version. In true Vegas fashion, it was purchased in cash but with an interesting payment structure that seemed more like a bet against the new owners. It changed hands for $12 million up front, with escalating monthly payments for 11 years, like a car leasing agreement. And like a leasing agreement, if payments stopped, then the URL would go back to the original owner unless the LVCVA kept paying for another 24 years of monthly payments. They must still be making payments though, as the site is still going.

1 CarInsurance.com

A cool $49.7 million the last time this URL changed ownership

Online marketing agency Quinstreet went through a series of high-profile URL purchases in the late 00s, grabbing the URL rights to CarInsurance.com for a sweet premium of $49.7 million (via DomainNameWire). That colossal purchase was just the feather in their cap, though, as they already owned similar URLs, Insure.com (cost $16 million) and Insurance.com (cost $35.6 million). Oh, and they also own Internet.com ($18 million), so their portfolio is pretty impressive. All of these were purchased after the dot.com bubble popped, and are still in use today for those shopping for insurance quotes.

Snappy, short URLs can make or break your company, and so can the amount of cash it takes to purchase them

When looking for a suitable URL for your business needs, the shorter, the better. Many SEO companies say it should be no more than ten letters, and the more recognizable the word(s), the more marketable it is. It should also be on a reputable TLD, like .com, or one specific to the country you mainly operate in. But to get those URLs today, you'd better break open the piggy bank because if anyone is actually going to sell you a short URL, it will be for an unholy amount of money.