Mr. O’Shields’ practice is focused on commercial real estate transactions, with an emphasis on development of housing, including affordable housing; development projects in downtown areas; land title matters; title insurance, including claims defense; public finance, advising utility companies in matters involving the operational aspects of utilities and the purchase and sale of utility systems.


  • Presenter at numerous seminars on various title insurance and real estate topics

Representative Matters

  • Redevelopment projects for hotel and housing developments in downtown Jacksonville  and waterfront redevelopment, and development agreements, including structuring and obtaining of economic development incentives.
  • Involved in numerous housing issues, including acting as bond counsel or developer's counsel in tax-exempt financings involving multi-family and single-family housing projects, and advising several different non-profit corporations in connection with their housing programs.
  • Represented a national title insurance underwriting company as its interim Florida underwriting counsel on two occasions, and represented several national title insurance companies in the administration of title insurance claims.
  • Representation of water and sewer utility companies in the negotiation of various utility service agreements and the sale of water and sewer utility systems to both private and governmental purchasers of those systems.

Areas of Practice


  • University of South Carolina B.A. 1972
  • Duke University School of Law J.D. 1976
  • Jacksonville University M.B.A. 2002
  • University of North Florida M.A., History 2010

Bar Association Memberships

  • The Florida Bar

Legal Certifications

  • Board Certified in Real Estate Law, The Florida Bar

Awards and Distinctions

  • AV Preeminent® Rating, Martindale-Hubbell
  • The Best Lawyers in America® (Real Estate Law), 2013-2014, 2016-2020
  • Recipient, Pro Bono Award, Jacksonville Area Legal Aid, 2007
  • Florida Super Lawyers® (Real Estate), 2006
  • Recipient, 12 Who Care Award for community volunteer work, 2002
  • Recipient, Blue Chip Award, Jacksonville University, 2004
  • Member, Phi Beta Kappa
  • Member, Omicron Delta Kappa

Professional and Community Involvement

  • Member, Florida Bar Grievance Committee
  • Sunday School Teacher, Youth Worker, Three-time Vestry Member, St. John's Episcopal Cathedral
  • Participant, Cursillo, St. John's Episcopal Cathedral
  • Mentor, Education for Ministry (EFM) Group, St. John's Episcopal Cathedral
  • Director Emeritus, Chairperson of Real Estate Committee, Clara White Mission
  • Past President of the Board of Trustees, Episcopal Child Day Care and Development Centers
  • Former Member, Board of Directors, Jacksonville Urban League
  • Pro Bono Service, Jacksonville Area Legal Aid