1931-2026: Anne Bailey built community through local newspaper

When Anne Bailey and her husband, George, moved to Winter Garden in 1970 as the new owners of the weekly newspaper, she wasn’t sure how residents would react to “outsiders” sharing their news and stories. But the community welcomed the Baileys and their four sons to West Orange County, where the family worked together to expand a local treasure with their personal touches and a passion for keeping people “in the know.”

The Baileys continued the tradition for 44 years, changing the newspaper name several times to reflect the growing community surrounding Winter Garden — from The Winter Garden Times to The Times to The West Orange Times. Anne Bailey served as editor and writer, documenting the stories of West Orange County and giving residents a place to announce their engagements, weddings, growing families, fundraisers, school news and more. She also wrote about her family, neighbors and friends in her Editor’s Notebook column in the 1980s and ’90s.

Anne Bailey, of Ocoee, died Friday, Feb. 6, 2026, at the age of 94.

Anne Stevens Bailey’s life began in New England — she was born in Wallingford, Connecticut, in 1931 to Evarts and Jane Stevens. She was well-educated, attending Abbot Academy, a girls’ preparatory school in Andover, Massachusetts, and graduating with a bachelor’s degree in 1953 from the private women’s school Smith College. 

She was working at the Young & Rubicam advertising agency in New York when she met her future husband, an agency executive, at a Christmas Eve party. Five months later, Anne and George Bailey were married in New York City. 

They lived in different parts of the country as their family grew. After the Baileys moved to Winter Garden with their four sons — ranging in age from 9 to 16 — they made West Orange County their home for the remainder of their lives.

The newspaper truly was a family affair, as all six folded and addressed newspapers on the living room floor each Tuesday night after George Bailey brought the bundles home from the Winter Haven printer in the back of his station wagon.

The newspaper grew in the Bailey era.

“They expanded it because there was attention being given to it,” said Andrew Bailey, one of the sons. “It went through a lot of different phases. … My parents became involved in it, and my dad with his advertising background, he within a couple of years had gotten grocery accounts. It was certainly a little more legitimate after a few years.”

In 1996, the West Orange Chamber of Commerce presented Anne Bailey with the inaugural Athena Award for her “exemplary accomplishment and leadership as a businesswoman and in recognition of (her) dedicated service to the West Orange community.”

The Bailey family celebrated Anne and George’s 50th wedding anniversary in 2004 at Windermere Town Hall. After George Bailey’s death in 2008, Anne Bailey continued as newspaper co-owner with their son, Andrew Bailey. She worked there on a limited basis until the newspaper was sold in 2014.

When she wasn’t writing stories and manually laying out the newspaper pages, Anne Bailey still maintained a connection to the community, delivering food to homebound senior citizens for many years with the Meals on Wheels program.

It was through Meals on Wheels that she met Ted Van Deventer, another volunteer who lived in the area. In their later years, the two were companions until his death in 2020.

She also was a decades-long member of Church of the Messiah in Winter Garden.

Andrew Bailey remembers his mother as someone who always was creative but who preferred to operate in the background.

“She serviced my dad’s whims, but she was the creative force behind it,” he said. “My relationship with my mother was probably different than others because I worked with her for so many years and then I lived with her and took care of her.”

Anne Bailey was preceded in death by two sons, Terry (1979) and Steve (1981); her husband of 54 years, George (2008); her brother, John; and a niece, Suzy Alarcon.

Besides Andrew Bailey, Anne Bailey is survived by her youngest son, John; sister-in-law, Ann Stevens; grandchildren, Laura (and Ralf) Vidal, John Bailey Jr., Erin (and Rees) Hoover and Zach (and Tara) Bailey; great-grandchildren, Audrey, Orien, Arden, Cannon, Barrett, Julia Jade, Hollis and Drew (whose birth is expected in April); and nieces and nephews, Mike Green, Patricia Green, Alice Dunning, Molly Malloy, Nancy Tobin, Judy Green, Karen Hutchinson and Ken Stevens. 

Funeral services will be held at 11 a.m. Friday, May 8, at Church of the Messiah, 241 N. Main St., Winter Garden.