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Clifford B Sheper
fl-bar-white-small-board certified
Best Lawyers - Lawyer Logo - CBS
Avvo rating 10.0

Clifford B. Shepard obtained his undergraduate degree in journalism and graduated law school from the University of Florida, where he was a member of the Trial Competition Team, Managing Editor of The Verdict, and a member of the law school’s student government.

Cliff’s practice developed in the areas of local government law, complex commercial and business litigation, community redevelopment, land use, real estate development, insurance defense, construction law, and homeowner and condominium association representation. He is also a Florida Supreme Court Certified circuit and appellate mediator and an approved agent for Attorneys’ Title Fund.

In 1995, Cliff attained the AV rating from Martindale-Hubbell and is listed in the Bar Register of Preeminent Lawyers®. He is Board Certified by The Florida Bar in City, County and Local Government Law.

Cliff has been named as one of The Best Lawyers in America© and Orlando’s Best Lawyers since 2018 in Administrative & Regulatory Law. Recognition by Best Lawyers is based entirely on peer review.

Best Lawyers’ methodology is designed to capture, as accurately as possible, the consensus opinion of leading lawyers about the professional abilities of their colleagues within the same geographical area and legal practice area.

Florida Trend Magazine has routinely recognized Cliff as one of Florida’s Legal Elite in the areas of Governmental and Administrative Law, and Commercial Litigation. Each year, the magazine names a new group of top lawyers who have earned

the confidence of those who know their work the best. Attorneys and judges throughout Florida were asked to name lawyers whom they hold in the highest regard – lawyers they have worked with or would recommend to others. The Legal Elite represents the top 1% of the Florida Bar members who practice in the state. Cliff is also among “Florida Super Lawyers”® as named by Law & Politics Magazine since 2006. “Florida Super Lawyers”® is a consumer’s guide to the best attorneys in the state.

Cliff is City Attorney for the Cities of Maitland and Apopka, and Town Attorney for the Towns of Ponce Inlet and Eatonville. He also serves as land use counsel to the cities of New Smyrna Beach, Satellite Beach, and several other cities and counties around Florida. He is General Counsel for the Florida Redevelopment Association and multiple CRAs throughout Florida.

Cliff is a member in good standing of the Florida (1985), Tennessee (2006), and District of Columbia Bar Association (1988). He is a current member of the City, County, and Local Government Law Section of the Florida Bar and the Florida Municipal Attorneys’ Association. He is also an active member of a number of professional organizations and has served as:

  • Past President of the Mid-Florida Chapter of the Community Associations Institute, a national clearinghouse for information on community associations issues;

  • Past-chair of the editorial board of the Florida Bar Journal and News, the two major professional publications for The Florida Bar; and,

  • Past member of the Florida Bar Judicial Selection, Administration, and Tenure Committee.


Cliff is a frequent speaker at continuing education seminars and has been a presenter on issues involving land use, Sunshine law, public records law, ethics for municipal officials, special districts, local government law, charter review, CRAs, construction defense, real estate, and association law, and has written several articles within these areas.


Community service has also been a staple of Cliff’s personal and professional life. Cliff has served on the Board of Directors for The Christ School. He served as a member of the Land Planning Agency for the City of Oviedo, and the Board of Directors of Big Brothers/Big Sisters of Central Florida. He also served as the Chairman of the Board for Kids Beating Cancer, Inc., a multiple award-winning local charity that assists families touched by childhood cancer. Cliff also serves as a court-appointed guardian-ad-litem to children who have been abused, abandoned, or neglected by their parents.


He and his wife Mary have three children – Tyler, Morgan, and Spencer.

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