Zillow.com Chief Executive Rich Barton doesn't think small. And neither do his investors. Barton's Seattle online real estate startup has scored an additional $30 million from Legg Mason Capital Management and existing investors – a huge capital infusion that comes just 19 months after the company unveiled its online home valuation service.

It ties Zillow with n2N Commerce as the largest recipient of venture funding this year in the Web 2.0 category, according to Dow Jones VentureOne.

Total financing now stands at $87 million, making Zillow one of the most heavily funded Internet startups in the country.

"Big opportunities command big investments," said Barton in explaining the need for the fresh round of capital.

The money – which Barton hopes will carry the startup to profitability – will be used for employment growth and new product development. One of the products – set to launch in the next three months – is a tool that will allow real estate brokerages to quickly upload hundreds or thousands of for-sale listings to the Zillow site. That's important because the company has relied on individual agents or homeowners to add for-sale listings, meaning that visitors to the site would only see a small percentage of the homes for sale in selected neighborhoods.

Zillow has already signed up some real estate brokerages who have agreed to provide listings, though Barton declined to disclose names.

Zillow also is working on a mortgage offering, which Barton said will "bring Zillow-like transparency and control and power to consumers in and around their homes."
All together, he thinks the company is doing things differently than online real estate players such as HouseValues, PropertyShark, Redfin and Trulia.

"It is not just people looking up what is for sale. Pretty much every other site in what you think of in the real estate category, that is what they are doing," he said. "We are a pretty different animal."

Barton, who turned 40 in June, knows about big opportunities. Prior to founding Zillow, he served as chief executive of Expedia – the online travel juggernaut now valued at more than $9 billion.

Barton believes that Zillow, which is attracting more than 4 million visitors per month who visit the Web site to check home values, list homes for sale or find neighborhood information, could one day surpass Expedia in terms of value.

"When we sold Expedia it was sold at about a $10 billion valuation and I tell you personally, long-term I am more excited about the opportunity for Zillow than I was for Expedia," he said. "It is a bigger business."

It's a bold claim, but Barton is confident that he can build a new online company whose ultimate goal is to create a "virtual town square" where people exchange ideas about everything from neighborhood restaurants to plumber recommendations to housing valuations.

"Rich thinks big," said Redfin Chief Executive Glenn Kelman, whose Seattle online real estate service advertises on Zillow and uses its home valuation technology. "Different startups operate on different scales. Zillow operates on a magnificent scale."

The latest funding round is evidence of that. Investors – including Benchmark Capital, Technology Crossover Ventures and Par Capital – are placing an enormous bet on an idea that is still in the early stages.

Barton declined to disclose revenue figures, but he admits that the 155-person company just started focusing on those opportunities.

Some of the money from the most recent venture round will be used to add sales staff. That department – now under the direction of former Yahoo and DoubleClick sales executive Greg Schwartz – has grown from two people to 20 in the past year.

Those sales staffers are focused almost entirely on online advertising, a model that Barton believes will continue to grow despite the recent housing slump.

"The volume of advertising dollars that are going after these people as they have these conversations around spending money, it is effectively infinite. It is so huge," said Barton. "It is the biggest advertising category."

Barton also bristles at the notion that his company could be following the get-big-fast model of some of the failed Internet companies from the last dot-com boom. The $87 million that Zillow has raised comes pretty close to some of Seattle's highest fliers of that era: Mercata ($90 million), FreeInternet.com ($89 million) and Rivals.com ($70 million).

Barton, who also serves as a venture partner at Benchmark Capital, said that a big difference is that many of those companies spent heavily on marketing in order to drive users. Zillow, he said, attracted millions of users through grass-roots efforts.

But there are similarities between Zillow and some of the companies of the late 1990s, most importantly a swing-for-the-fence attitude that many startups today don't share. Barton – who discussed the possibility of one day taking Zillow public – has a go big or go home attitude that investors love. And he says he would never consider doing a quick flip of a business, as is the case with some Web 2.0 ventures today.

"That is completely anathema to me," he said. "I hate that. That is ridiculous. People aren't trying to create long-term brands and long-term value. That is like house flippers… We are not creating a feature here, we are creating a business for the long term that is going to be a brand that my grand kids know."

Barton – who spent nearly a decade building Expedia – says he is a patient guy. But the question remains whether his investors, with $87 million on the table, will take the same long-term view.