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Clifford B. Shepard holds the AV rating from Martindale-Hubbell and is listed in the Bar Register of Preeminent Lawyers®. Cliff is a trial lawyer who practices and mediates extensively in the areas of government law, employment, defense, real estate, construction law, complex commercial litigation, and community association law. He is Board Certified by The Florida Bar in City, County and Local Government Law. He is the City Attorney for Maitland and Apopka and Town Attorney for the Towns of Ponce Inlet and Eatonville. He is also General Counsel for the Florida Redevelopment Association and multiple CRAs around the state. Additionally, Cliff is a certified Circuit Court and Appellate mediator and an approved agent for Attorneys’ Title Fund. Cliff is one of The Best Lawyers in America© and listed in Orlando’s Best Lawyers in Administrative & Regulatory Law. Florida Trend Magazine also recognizes Cliff as one of Florida’s Legal Elite in the areas of Governmental and Administrative Law and Commercial Litigation. Cliff is a “Florida Super Lawyers”® by Law & Politics Magazine. Cliff is a member in good standing of the Florida (1985), Tennessee (2006), and District of Columbia (1988) Bar Associations and is a current member of the City, County, and Local Government Law Section of the Florida Bar and the Florida Municipal Attorneys’ Association. While Cliff has served as an active member of a number of professional organizations, of particular note is his service as Past President of the Mid-Florida Chapter of the Community Associations Institute, a national clearinghouse for information on community associations issues; Past-chair and current member of the editorial board of the Florida Bar Journal and News, the two major professional publications for The Florida Bar; Past member of the Florida Bar Judicial Selection, Administration and Tenure Committee.

Cliff is a frequent speaker at continuing education seminars and presents on issues involving special districts, local government law, CRAs, construction, defense, real estate, and association law and has written several articles within these areas. Community service is also a staple of Cliff’s personal and professional life. Cliff has served on the Board of Directors for The Christ School, a private K-8 school in downtown Orlando. He has served as a member of the Land Planning Agency for the City of Oviedo and as a member of the Board of Directors of Big Brothers/Big Sisters of Central Florida. He has also served as the Chairman of the Board for Kids Beating Cancer, Inc. This multiple award-winning local charity assists families touched by childhood cancer through the recruitment, DNA testing, and matching of potential bone marrow donors to patients whose best hope for a cure is a bone marrow transplant. Cliff also serves as a court-appointed guardian-ad-litem to children who have been abused, abandoned, or neglected by their parents. He is married to his wife, Mary, and has three adult children.

Contact & Links
Location
  • 2300 Maitland Center Parkway, Suite 100
    Maitland, FL 32751
Demographics
  • Gender: Male
Education
  • University of Florida, Juris Doctorate, graduated 1985
  • University of Florida, B.S. in Journalism, graduated 1981
Bar Admissions
  • Florida, 1985
  • District of Columbia, 1988
  • Tennessee, 2006
Affiliations
  • Federal Bar Association - Member
Court Admissions
  • United States Supreme Court
  • United States District Court - all Florida districts
  • United States Tax Court

Recognized in The Best Lawyers in America® 2025 for work in:
  • Administrative / Regulatory Law
Special Focus:
  • Litigation
Awards:
  • Best Lawyers in America

  • Florida Legal Elite
  • Florida Super Lawyer
Additional Areas of Practice:
  • Appellate Practice
  • Bet-the-Company Litigation
  • Commercial Litigation
  • Economic Development Law
  • Government Contracts
  • Government Relations Practice
  • Land Use and Zoning Law
  • Litigation - Municipal
  • Municipal Law
  • Real Estate Law

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