Jonathan C. Squires - Attorney at Law

301 East Pine Street
Suite 1400
Post Office Box 3068 (32802-3068)
Orlando, Florida 32801

P 407-843-8880
F 407-244-5690

  • Download Attorney Contact Information

Jon is a transactional attorney in GrayRobinson’s Orlando office. He has broad experience with real estate deals of all types. Jon has represented both buyers and sellers of residential and commercial properties, landlords and tenants of commercial properties, commercial developers, as well as borrowers and lenders involved with real estate and asset back loans. He also has represented buyers and sellers of businesses, both in asset-centered and stock-centered transactions.

Jon also practices in the area of taxation. He advises clients on the state, local and international tax implications of their business plans. His knowledge of French, Italian and Spanish helps him serve the needs of clients doing business in Florida, regardless of their country of origin.

Additional Information About Jonathan C. Squires

Expand All  |  Collapse All
Click the "+" to Expand the Sections Below
Click the "-" to Collapse the Sections Below


Jon is a seventh generation Floridian and grew up in Orlando. He attended Trinity Preparatory School, and later graduated from Davidson College with a bachelor’s degree in political science. After graduating, he attended law school at the University of Miami, where he graduated magna cum laude and was a member of both the University of Miami Law Review and Moot Court Board. While in law school, Jon worked for both Anne C. Conway, Chief Judge of the U.S. District Court, Middle District of Florida, and the Department of Homeland Security. Jon later obtained a Masters of Laws in Taxation from the University of Florida graduate tax program, one of the most highly recognized programs of its type in the United States. He has prior work experience at both AmLaw100 and AmLaw 200 firms.

  • Davidson College, B.A. political science (2006)
    • Sigma Phi Epsilon
    • NAQT National College Quizbowl Team, 7th place nationally
  • University of Miami School of Law, J.D. (magna cum laude, 2009)
    • University of Miami Law Review, Editor
    • Charles C. Papy, Jr. Moot Court Board
    • National Order of Barristers
    • Order of the Coif
    • Dean’s Certificate of Achievement in Real Property and Criminal Procedure
    • Co-Author, Note, Free Falling With a Parachute That May Not Open: Debtor-In-Possession Financing in the Wake of the Great Recession, 63 U. Miami L. Rev. 1205 (2009)
  • University of Florida Levin College of Law, LL.M. taxation (2012)
  • Florida
Professional Associations & Memberships
  • The Florida Bar
    • Tax and Real Property, Probate and Trust Law sections
  • Orange County Bar Association
  • Orlando Area Committee on Foreign Relations
  • Trinity Preparatory Alumni Advisory Board
  • French
  • Italian
  • Spanish
Representative Experience

Real Estate

  • Represents purchasers and sellers of residential properties, including multi-million dollar properties and properties with title defects.
  • Represents buyers and sellers in multi-million dollar transactions involving multi-acre commercial parcels, some in excess of 1,000 acres, including 1031 like-kind exchanges and seller-financed projects.
  • Represents buyers and sellers of, hotels and resorts, condominiums, and multi-family housing projects, including related CMBS and defeasance matters.
  • Negotiates and drafts commercial leases for national and local landlords and tenants for outparcels, strip centers, and vertical developments.
  • Represents developers and builders in the negotiation and closing of lot takedown agreements.
  • Assists in drafting and analyzing governing documents for condominiums and homeowner’s associations.
  • Represents homeowners in variance applications before local government authorities.


  • Incorporates and dissolves various business entities.
  • Drafts bylaws, operating agreements, and partnership agreements.
  • Assists in restructuring and reorganization of corporate holding structure for real estate holding companies.
  • Assists in purchases and sales of companies in both asset-based and stock-based transactions.
  • Negotiates business contracts for numerous different industries, including but not limited to biomass/biofuel, mobility aids, construction services, and tablet pcs.

Banking and Finance

  • Represents borrowers and lenders in asset-based, real estate-based, and mezzanine secured lending, including multi-million dollar transactions.
  • Conducts due diligence of borrowers and properties, including but not limited to survey, title, local ordinances, corporate records, etc.
  • Represents lenders in the purchase, sale, assignment and assumption of loans, including packages of multiple loans and underperforming assets.
  • Reviews terms of security instruments to ensure proper pledging and collateralization of loans, letters of credit, certificates of deposit, and other financial products.


  • Advises clients about State of Florida tax issues, including but not limited to documentary stamp taxes, intangible taxes, and sales and use taxes.
  • Reviews terms of foreign trust instruments with U.S. beneficiaries to advise clients of potential income tax implications.
  • Reviews terms of joint venture agreements and partnership agreements to ensure proper tax treatment of projects based on client objectives.
  • Represents taxpayers in disputes before the IRS in individual, corporate, partnership, payroll and international tax disputes.

Health Care

  • Assists clients under a CMS investigation for unauthorized billing practices.
  • Drafts numerous leases for medical office buildings.
  • Assists in due diligence and document preparation in advance of proposed $100 million acquisition of HMO.
Articles & Publications
  • Co-Author, Note, "Free Falling With a Parachute That May Not Open: Debtor-In-Possession Financing in the Wake of the Great Recession," 63 U. Miami L. Rev. 1205 (2009)
  • YouTube
  • Twitter
  • Facebook
  • LinkedIn
  • Ingenuity in Action.TM

To contact your closest G|R Office call 800-338-3381

Subscribe to Our E-mail List: