Past President and Banker’s Cup Winner Judy Cleaves Retires

Published: Sunday, October 12, 2014 at 9:42 p.m.
Last Modified: Sunday, October 12, 2014 at 9:42 p.m.

WINTER HAVEN | In the business of selling houses, Judy Cleaves has long been a household name.

The owner of Winter Haven-based Judy B. Cleaves Properties officially retired this month, bringing an end to a 35-year career in real estate.

“I’ve been saying I want to stop while I’m ahead and I feel good and can enjoy life,” said Cleaves, 74. “I don’t want someone tapping me on the shoulder saying, ‘Oh, you shouldn’t be doing that anymore.’ “

There is still a full itinerary ahead: time with grandchildren, games of bridge and trips to Sarasota, where Cleaves has been a devoted admirer of the local arts scene.

And this isn’t the last you’ll hear of her name. An associate, Carol Sheil, has purchased the real estate business and will continue to operate it as Judy B. Cleaves Properties. Cleaves herself will remain among the six agents on the firm’s roster — “just in case,” she says with a laugh.

“I’m not going anywhere, I’m just not going to be working so hard.”

Looking back, Cleaves said her career began as a way to prove something to herself.

A native of Savannah, Ga., and valedictorian of her high school, she moved to Winter Haven with her parents in 1957.

Going off to college was not an expectation of the young women of Cleaves’ generation, she said. She spent a year at the University of Florida anyway, before getting married and starting a family with three children.

In the late 1970s Cleaves found herself in need of a job, and she got into home sales when a local agent suggested she would be good at it.

She spent nine years with a company in Winter Haven before establishing her own firm in 1989. At the time, Cleaves knew of only a small handful of female Realtors in the area who had done the same.

“I think one of the reasons I worked so hard was to prove to myself that I could succeed even though I didn’t have the opportunity to finish college,” she said. “I did self-educate. I took classes for the management of the company. I owe a lot of my success to that.”

Longtime friend Bonnie Parker said she admires Cleaves for her acumen and drive.

“She has a way of having that Savannah charm that makes her seem understated, but I can assure you she is highly intelligent. She’s well-traveled, cultured, and well-read,” said Parker, a senior vice president with Citizens Bank and Trust in Winter Haven. “She’s been a good role model for me as a businesswoman.”

In a momentous step during the business’ early days, Cleaves hired Chris Nikdel — now the CEO and art director of Winter Haven’s Clark/Nikdel/Powell — to design a logo.

She developed with a little orange house surrounded by two green trees, which is still in use today.

Cleaves had the logo emblazoned on contact paper and used it to adorn the mailboxes of her homes for sale.

“People loved them, they loved them. They were cute, they looked friendly,” she said. “That helped get me going. It was good promotion.”

She also raised her profile by getting involved in the community.

Cleaves has served as president of Winter Haven’s Rotary Club and Chamber of Commerce, and has been involved with organizations including Girls Inc. and the Polk Museum of Art.

“Winter Haven is a very special community,” she said. “If you support them, they’ll support you, and I’ve had huge support from the community.”

She also has served in multiple leadership roles with the East Polk County Association of Realtors, and was named Realtor of the Year in 1994.

When Cleaves announced her

retirement to her firm’s associates in June, Sheil scrambled to obtain her broker’s license and purchase the business.

“Judy has such a spectacular reputation throughout the community, and has been so involved that it just made sense to keep the name,” said Sheil, who has worked in real estate for about 15 years after a previous career in nursing and health care. “It’s carrying on a tradition of integrity and good service.”

The business has relocated from Central Avenue to an office at 131 Fifth Street NW, facing the park in downtown Winter Haven.

There are no other changes to the business planned for the near future.

“I can still do referrals and consult. I can be around if they need me,” Cleaves said. “I love people and I enjoy the real estate business; I totally invested myself in it … it’s been a wonderful life for me.”

[ Kyle Kennedy can be reached at or 863-802-7584. ]

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3 Responses to Past President and Banker’s Cup Winner Judy Cleaves Retires

  1. Eddie Allen says:

    Thanks Judy, for all you have done for Winter Haven & especially your work with Rotary Club of Winter Haven.

    Good Luck to you!!
    Eddie Allen, President
    Rotary Club of Winter Haven

  2. Judy,
    We shall miss you, it has always been one of our greatest pleasures to work with you, and we have sold many home with you over the 20 years…. Now is the time for those Grand Children, enjoy them and keep in touch!!
    Congratulations from Michael and Dee Norris.

  3. Howard Beckert says:

    Congratulations, Judy on a wonderful career. You brought professionalism, class and leadership to our community.

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