Lauren Oakley Schwenk

Lauren Oakley Schwenk

Emerging Polk Leader Who is Making a Difference


Lauren Oakley Schwenk grew up in Winter Haven, graduated from Winter Haven High School, and when she left to go to college and begin her career, she said she “didn’t plan on coming back. Now I love it here. I am working on bringing other young people back to Winter Haven.”

This 32-year-old brunette beauty with a million dollar smile left Winter Haven in 1998 to attend the University of Florida, transferred to the University of Central Florida, and graduated from there in 2002 with a degree in Marketing. “I didn’t know what path I was going to take, but real estate and land development interested me.” After working for a year as Marketing Director for an apparel company in Orlando, she procured her real estate salesperson license and landed a job with Keller William Classic Realty in Orlando.

Remember, she was never going to come back to Winter Haven. Then as luck and serendipity would have it, she crossed paths with Albert Cassidy (owner of Cassidy Homes) at a UF football game. They started talking and from that conversation, she came back to Winter Haven and worked for five years with the land development company of Highland-Cassidy, LLC, overseeing thirty-two projects at different stages of development, from contract to final platting.


Not one to let grass grow under her feet, she decided it was time to strike out on her own. In December 2008, with five other partners, she formed Oakley Rhinehart Cassidy,LLC, a real estate investment, rental ownership, HOA management and land development company based in Winter Haven. She is a managing partner with Michelle Bannon, Al Cassidy (son of Albert Cassidy), Andrew Rhinehart, Nick Rhinehart, and Adam Rhinehart, all up and coming young professionals. In 2009, with Michelle Bannon, Rennie Heath and Mark Shabla, she formed and is managing partner of Magnolia Investments; a real estate investment

company that manages for future development, 290 acres of developable land adjacent to the new CSX Facility in Winter Haven. Not one to remain idle, in 2010 with Michelle Bannon and Al Cassidy, she formed and became part owner of Creative Association Services, an HOA (Home Owner’s Association) Management company which provides accounting and managements services to 1,425 units in 13 Winter Haven and Tampa communities, and oversees operation of landscaping crews which service Orchid Springs and Park Lake, two large Winter Haven developments.
Of her businesses and her partners – all bright and industrious young professionals – she says, “It is like a family business in a lot of respects. We always talk and we have enough partners for any new challenges and direction.”

Although her businesses require her to work a lot of weekends and evenings, “It’s fun to be at work,” she said. That doesn’t stop her from being involved in the community and staying fit. She received the Winter Haven chamber of Commerce 2011 Polk Emerging Leaders Award. She has raised thousands of dollars for the Stroke Center at Winter Haven Hospital. (Her parents, Tommy and Lynn Oakley, are big supporters of WHH.) She “stepped out for education” in 2012 by performing the Argentine Tango and the Swing as a celebrity dancer at the Polk Education Foundation annual fundraiser. She co-chairs Aspire Winter Haven – an organization to inspire people to want to come back to the area. She also is currently on the Domestic Violence Safety Net Taskforce, was Wine for Wisdom chairperson in 2011 and is still a committee member, is a graduate of the 29th Winter Haven Chamber Leadership Class. She sits on many professional boards and committees, too numerous to mention all, but include City of Winter Haven Planning Commission, Polk State College Foundation.

City of Winter Haven Affordable Housing Committee, Winter Haven Vision Steering Committee, and a half-dozen more.



Her trim, fit figure doesn’t happen by chance. She works out at Habitat Health and Fitness (similar to a boot camp) two times a week, and twice a week with a trainer at Gold’s Gym, and also does yoga at Groundwork Yoga. Her trainer has had a lot to do with Lauren’s future. He introduced her to Zane Schwenk, a world renowned professional wake boarder who entertained at Cypress Gardens for eight years and is now a pro rider – helping design and market – and southeast sales rep with MasterCraft boats. The pair married in 2011.

After Lauren received the 2011 Polk Emerging Leader award, she noted, “I now believe that my generation has some of the greatest opportunities that this area has ever seen. From Legoland and CSX, to the Polytechnic to Polk State College; our area is building the groundwork for a strong community built on education and job growth.”

It seems as though Lauren Oakley Schwenk is truly a Polk Emerging Leader and is here to stay.



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