Observer Media Group buys The West Orange Times

After more than four decades, the Bailey family, of Winter Garden, has sold The West Orange Times, a weekly community newspaper that has served West Orange County for nearly a century. The sale closed on Monday.

The buyer, Observer Media Group Inc., is owned by Matt and Lisa Walsh, who publish eight other weekly newspapers in Florida.

“Our family is happy to have the Walshes continue the legacy of The West Orange Times,” said longtime Publisher Andrew Bailey, who, with his mother, Anne Bailey, owned the Times. “We were fortunate to sell our newspaper to friends who have a long history in community journalism.”

George and Anne Bailey bought The Winter Garden Times in 1970 from The Winter Haven News Chief. Their son, Andrew Bailey, has been publisher for more than 25 years.

Matt Walsh, CEO of Observer Media Group, said he’s excited about the venture.

“We are thrilled, honored and privileged that the Bailey family has entrusted us to be the next stewards of The West Orange Times,” Walsh said. “And we intend to build on the Times’ tradition of being an involved and essential part of the communities of Winter Garden, Windermere, Ocoee, Oakland and West Orange County.”

The Walshes have been working in the newspaper business in Florida since 1980 and started their company in 1995.

Dawn Willis is the new publisher of The West Orange Times.

She joins the Observer Media Group with 12 years of media experience with Halifax Media Group and the New York Times, in addition to 20 years of experience in management and marketing. She most recently served as the director of advertising and marketing for two daily newspapers and websites in Polk County, The Ledger and The News Chief and a weekly product, the Polk Voice. She was also the editor of Inside Polk Magazine.

Willis said she believes in partnering and serving in the community. She served on several boards in Polk County, including the Salvation Army Board of Directors, United Way Women's Leadership Council and the Kiwanis Club.

Willis said she “is thrilled to be joining the Observer Media Group and honored to lead the award-winning West Orange Times” in her new role.

“I am proud to carry on the history and tradition of The West Orange Times and the Bailey family,” she said.

In addition to its eight (now nine) newspapers, the Observer Media Group publishes six websites and two lifestyle magazines and operates a digital advertising and marketing agency. The company’s publications reach more than 270,000 readers and viewers a week.

The newspapers include the Sarasota, Longboat, Palm Coast and Ormond Beach and East County Observers; the Business Observer; and the Pelican Press; and the Plant City Times & Observer, a joint venture with the Tampa Bay Times.

The company employs 100 in offices that stretch from Naples to Tampa and east to Palm Coast.