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About me

Clifford B. Shepard obtained his undergraduate degree in journalism (News Writing and Editing) and graduated law school from the University of Florida, where he was a member of the Trial Competition Team, Managing Editor of The Verdict student newspaper, and a member of the law school's student government.  He moved to Orlando in 1985 and began law practice.


Cliff's practice developed in the areas of local government law, complex commercial litigation, real estate development, insurance defense and construction law, as well as homeowner and condominium association representation, an area he developed after serving as association president to a 2400 home development in Seminole County.  In 1995, Cliff attained the AV rating from Martindale-Hubbell, and is listed in the Bar Register of Preeminent Lawyers®.  Cliff 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 and an approved agent for Attorney's Title Insurance Fund.


In 1998 Cliff became "Special Counsel" to the City of Maitland, Florida in litigation and real estate matters and in 2002, was selected as City Attorney upon the retirement of the City's former counsel.  He also serves as City Attorney for Mount Dora, the Town Attorney for the Town of Ponce Inlet and the General Counsel for the Florida Redevelopment Association.  Additionally, Cliff is a certified Circuit Court mediator.


Cliff has been honored by Florida Trend Magazine as one of Florida's Legal Elite™ (2005-2009, 2011, 2013) 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™ represent the top 1.7% of the 56,513 Florida Bar members who practice in the state.   Cliff was also named a "Florida Super Lawyers"® (2005-2014) by Law & Politics Magazine.  "Florida Super Lawyers"® is a consumer's guide to the best attorneys in the state.


Cliff is a member in good standing of the Florida (1985), Tennessee (2006) and District of Columbia (1988) Bar Associations, is a current member of the City, County and Local Government Law Section of the Florida Bar.  While he 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 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 has been a presenter on issues involving special districts, local government law, construction, defense, real estate, and association law and has written a number of articles within these areas.


Community service has also been a staple of Cliff's personal and professional life.  Most recently he served on the Board of Trustees for The Christ School, a Christian K-8 private 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., a multiple award-winning local charity that 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 wife Mary, and has three children - Tyler, Morgan and Spencer.


Photos and videos

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Practice areas


  1. State, Local And Municipal Law: 40%
    18 years
  2. Litigation: 30%
    29 years
  3. Commercial: 15%
    29 years
  4. Real Estate: 15%
    26 years



Hourly ($190-350/hour)

Payment types:

Cash, Check

Attorney endorsements

3 total 

Are you an attorney? Endorse this lawyer

  • Mark Nickolas Longwell

    I endorse this lawyer.


    Mark Longwell Criminal Defense Attorney
    Relationship: Fellow lawyer in community

  • Robert Patrick Major

    I worked closely with Cliff on a complex litigation matter arising out of the suicide of Stephen R. Walsh and the related collapse of Walsh's real estate development companies including Broad Street Partners, LLC. Cliff is a superb lawyer. He has excellent analytical and communication skills, is passionate about his work, and is a pleasure to deal with. I strongly recommend and endorse him.


    Robert Major Litigation Attorney
    Relationship: Worked together on matter

Contact info

Shepard, Smith & Cassady, P.A.

2300 Maitland Center Parkway
Suite 100
Maitland, FL, 32751-5647


DCActive 198705/24/2015
FLMember in Good Standing198509/08/2015
We have not found any instances of professional misconduct for this lawyer.
Avvo contributions
Legal answers
Award nameGrantorDate granted
Florida Super LawyerLaw & Politics Magazine2012
Florida's Legal EliteFlorida Trend Magazine2011
Florida Super LawyerLaw & Politics Magazine2011
Florida Super LawyerLaw & Politics Magazine2010
Florida's Legal EliteFlorida Trend Magazine2009
Florida Super LawyerLaw & Politics Magazine2009
Florida Super LawyerLaw & Politics Magazine2008
Florida's Legal EliteFlorida Trend Magazine2008
Florida Super LawyerLaw & Politics Magazine2007
Florida's Legal EliteFlorida Trend Magazine2007
Board Certified - City, County & Local Government LawFlorida Bar2006
Florida's Legal EliteFlorida Trend Magazine2006
Florida Super LawyerLaw & Politics Magazine2006
Florida's Legal EliteFlorida Trend Magazine2005
Florida Super LawyerLaw & Politics Magazine2005
Bar Register of Preeminent AttorneysMartindale-Hubbell1995
AV RatedMartindale-Hubbell1995
Outstanding Chairman - Florida Bar Journal/NewsFlorida Bar1993
Pro Bono AwardOrange County Bar AssociationN/A
Work experience
TitleCompany nameDuration
PresidentShepard, Smith & Cassady, P.A.2008 - Present
ShareholderLangston, Hess, Shepard & Augustine, P.A.2004 - 2008
Managing PartnerShepard & Filburn, P.A.1994 - 2004
ShareholderKilgore, Pearlman et al.1988 - 1994
AssociateLitchford, Christopher et al.1987 - 1988
AssociateDempsey & Goldsmith, P.A.1985 - 1987
Association namePosition nameDuration
Tiger Bay ClubMember2006 - Present
Tennessee Bar AssociationMember2006 - Present
Florida Bar Journal/News Editorial BoardBoard Member2005 - Present
Florida Academy of Certified MediatorsMediator1999 - Present
Florida Municipal Attorneys AssociationMember1998 - Present
Florida Bar, City, County and Local Government Law SectionMember1998 - Present
District of Columbia Bar AssociationMember1987 - Present
Orange County Bar AssociationMember1985 - Present
Trial Competition Team - University of FloridaMember1984 - 1985
Legal cases
Case nameOutcome
Bekaert Specialty Films vs. Jeffrey Plummer, et al.Directed verdict in favor of Defendant Plummer on all counts.
Matthews et al. vs. City of Maitland, et al.Summary judgment for Maitland on all 11 counts.
Winter Park Construction vs. City of MaitlandSummary judgment for Maitland on all counts.
See all legal cases 
Publication nameTitleDate
Trial Magazine"Lost" Medical Records - Redefining the Scope of the Spoliation Doctrine1987
School nameMajorDegreeGraduated
University of Florida, Fredric G. Levin College of LawLawJD - Juris Doctor1985
University of FloridaJournalism and Mass CommunicationBS - Bachelor of Science1981
Speaking engagements
Conference nameTitleDate
FMAA Annual Meeting & SeminarCommunity Redevelopment2012
Annual ConferenceEssential Economic Development Law2011
Annual ConferenceBoard Training - Sunshine Law, Ethics, Public Records2011
30th Annual SeminarCharter Reviews in Florida2011
City, County & Local Government Section Annual MeetingSunshine Law & Social Media2010
Annual ConferenceThe Impact of Strand v. Escambia County on Redevelopment2007
Legal UpdateCommunity Association LawN/A