At the age of 14, Lloyd Frink began working at Microsoft as a product support personnel. This experience at a young age allowed him to gain valuable insights and skills that he later brought into Zillow.

The positive naivety and risk-taking culture inherited from Expedia played a significant role in shaping Zillow's approach to the real estate space. This influence brought a fresh perspective and a willingness to challenge traditional norms in the industry.

Zillow Group was founded in 1998 and has since become a major player in the real estate and housing market, providing online real estate databases and services.

Zillow Inc. files for incorporation in Washington, with Rich Barton as CEO and other key executives from Expedia. This marks the official beginning of Zillow's journey.

Inman News predicts that Zillow will have a significant impact on the real estate industry. The company's plans for an online marketplace for real estate listings are hinted through patent and trademark filings.

Zillow's website was launched on February 8, 2006, and included a home-valuation tool that anyone could use. Other features at the time included information about home sale history and charts and graphs comparing home value appreciation with other towns or states.

Even before the site launches, some are speculating it will force drastic change in the real estate industry -- fears that are fueled by revelations that Zillow has acquired real estate brokerage licenses in five states.

On April 2, 2006, Zillow forms a technical advisory board to provide independent advice on improving the technology and algorithms supporting the company's online services.

On October 5, 2006, a complaint is filed with the FTC over the valuations provided by Zillow.

The National Community Reinvestment Coalition files a complaint with the U.S. Federal Trade Commission, alleging that Zillow is providing misleading information to consumers and industry professionals about the accuracy of Zestimates. Zillow refutes the allegations, stating that Zestimates are meant to serve as a starting point.

Zillow acquires brokerage licenses in most states to ensure legal standing for publishing real estate information.

Arizona Board of Appraisal sends cease-and-desist letters.

On May 4, 2007, the Federal Trade Commission (FTC) decided not to investigate the complaint filed by the National Community Reinvestment Coalition against Zillow. The complaint was later withdrawn by the NCRC.

Zillow adds neighborhood pages with detailed demographic information for over 130 cities, allowing users to contribute photos, events, news, and engage in discussions and Q&A sessions.

Zillow announces its first agreement for the bulk upload of about 80,000 property listings from brokerages affiliated with franchise network ERA Franchise Systems LLC. This marks a shift from accepting listings individually from consumers and real estate agents to a bulk upload approach.

Realogy Corp. reveals its plan to feed 700,000 property listings from several brokerages to Zillow.com, expanding on the previous agreement between Zillow and ERA Franchise Systems. This significantly increases the number of listings on Zillow.com.

In March 19, 2008, Zillow entered into its first partnership with an MLS, New England-based MLS PIN, which agreed to feed 60,000 listings to Zillow.com.

On April 1, 2008, the blog Silicon Alley Insider estimated that Zillow is worth about $225 million.

On April 3, 2008, Zillow launched Zillow Mortgage Marketplace, providing a platform for borrowers to receive custom loan quotes without revealing personally identifying information.

On September 10, 2008, Zillow formed an advertising alliance with 11 newspaper publishers.

Zillow introduces its Premier Agent advertising program, aiming to provide real estate agents with a platform to promote their services to a wider audience.

Zillow announces a significant layoff, affecting 25% of its workforce, due to concerns about the impact of unprecedented economic events on the company's future.

Zillow decides to surrender its brokerage licenses in all states except for two, indicating a strategic shift in its business operations.

Zillow announces the relinquishment of its real estate brokerage licenses in all but two U.S. states, while maintaining its ability to publish real estate-related information.

Zillow releases its first mobile application, a free iPhone app that allows users to see their location on a map as they walk or drive through a neighborhood, pulling up details on about 95 percent of all U.S. homes.

Zillow starts to charge mortgage lenders who provide loan quotes to consumers through the Zillow Mortgage Marketplace.

CoreLogic files a lawsuit against Zillow and others.

Yahoo Real Estate and Zillow reached an agreement for Zillow to supply real estate listings to Yahoo Real Estate, granting Zillow the exclusive right to sell real estate agent advertising on the Yahoo Real Estate site.

Spencer Rascoff was promoted to the position of CEO.

Spencer Rascoff, a member of Zillow's original executive team, is promoted from chief operating officer to CEO. Co-founders Rich Barton and Lloyd Frink will continue to play an active role in the company, with Barton as chairman of the board of directors, and Frink as chief strategy officer.

Zillow and Yahoo Real Estate launched a program for real estate listings and advertising, marking a significant collaboration between the two companies.

Zillow.com introduced 'Rent Zestimates' for approximately 90 million homes or apartments, providing estimated rental prices whether the properties are available for rent or not.

Zillow's Premier Agent ad program achieved over 10,000 paying subscribers by the end of March 2011, as disclosed in a regulatory filing.

On April 18, 2011, Zillow filed for a $5.1 million initial public offering, which was a pivotal moment in the company's history. This move allowed Zillow to become a publicly traded company.

Zillow enters into a long-term agreement associated with ListHub, a significant development in its business operations.

On June 14, 2011, Zillow modified the algorithm used to calculate Zestimates. This change impacted the current Zestimate for millions of homes across the country, as well as historical Zestimate value information dating back to 2006.

Zillow's initial public offering (IPO) is officially announced.

In 2012, Zillow acquired RentJuice, a platform for managing rental properties, and Diverse Solutions, a provider of online marketing tools for real estate professionals.

In late 2013, Zillow started powering AOL Real Estate, indicating a significant partnership and expansion of its real estate services.

On July 25, 2014, Zillow celebrated its 9th anniversary.

In 2015, Zillow made a major acquisition by purchasing Trulia, a major competitor, in a $2.5 billion deal. This acquisition significantly expanded Zillow's market presence and influence.

Rich Barton, Spencer Rascoff, and Lloyd Frink, the co-founders of Zillow Group, were interviewed in downtown Seattle.

On February 26, 2016, the U.S. District Court for the Central District of California certified the class to include anyone who worked as an inside sales consultant at Zillow between November 2010 and January 2015. The lawsuit alleged violations of California Labor Code and California Business and Professions Code, including failure to pay wages, overtime pay, and provide meal and rest breaks.

On May 5, 2016, Zillow settled a sexual harassment action for an undisclosed amount, without admitting any wrongdoing. The action was represented by high-profile attorneys and alleged 'sexual torture' and 'the most heinous acts of sexual harassment imaginable' against a former Zillow employee.

In October 2017, Zillow announced the addition of three-dimensional tours to provide 360° photos of houses, enhancing the customer experience for those interested in buying or renting properties.

In April 2018, Zillow announced the launch of a new business, Zillow Offers, which involved buying and selling homes in partnerships with local brokerages and agents.

In June 2018, Zillow signed a partnership with Century 21 Canada to begin listing Canadian properties on the site, marking the company's expansion outside the United States.

In July 2018, Zillow released a tool for prospective renters to submit a credit check and eviction history report to landlords, offering a valuable service to both renters and landlords.

In February 2019, Rich Barton returned to the CEO role, replacing Rascoff.

In May 2019, Zillow announced the expansion of its home-buying business, Zillow Offers, to new markets.

In February 2020, Zillow's stock was up 18% after hitting a four-year low.

In March 2020, the company announced a 25% cut in expenses and paused hiring due to the COVID-19 pandemic.

In July 2020, Zillow became one of the first companies to let employees keep working from home indefinitely.

Premier Agent services remain Zillow's main source of revenue, as real estate agents mainly pay based on the number of ad impressions delivered to users in specified zip codes.

On June 15, 2021, Zillow reported an update in how it calculates the Zestimate for off-market homes. This update aimed to be more responsive to local trends and seasonality that may affect a home’s market value, and included even more historical data to enhance accuracy.

In October 2022, Zillow reported significant losses and a sharp decline in its share price, highlighting the financial challenges it encountered due to operational inefficiencies and market dynamics. The company's performance in 2022 reflected the impact of its strategic decisions and external factors.

Starting from January 2023, Zillow has upgraded the ZHVI time series to utilize the neural Zestimate for all subsequent releases.