Thomas R. Castiello

Partner and Real Estate Practice Leader
Tommy’s principal areas of focus are commercial real estate matters, joint ventures, transactional work, and finance.
Thomas Castiello, Partmer

Client Work

Tommy represents a wide variety of clients in all aspects of their real estate activities. He has extensive experience in acquisitions, joint ventures, financings, and dispositions involving a broad range of commercial real estate assets. Among other clients, Tommy has represented Goldman Sachs, DLC Management Corporation, DSC Partners LLC, Foulger-Pratt and Fannie Mae. 

In addition, Tommy has extensive experience working with numerous District of Columbia public charter schools in connection with, among other things, the acquisition, financing and development of campus facilities, including KIPP DC, Two Rivers Public Charter School, and DC Bilingual Public Charter School.

Tommy has also represented a number of clients in connection with the acquisition, financing, and disposition of professional sports franchises and sports and entertainment facilities.

Recent representations include:

  • Representing Goldman Sachs in connection with the disposition of several office towers in Charlotte, North Carolina.
  • Representing DSC Partners LLC in connection with the acquisition and financing of a 28-building portfolio in Montgomery County, Maryland, as well as the acquisition and financing of a 15-office building portfolio in Chesapeake and Norfolk, Virginia.
  • Representing KIPP DC in connection with the acquisition and financing of the Ferebee-Hope Campus, which will serve as KIPP DC’s second high school campus. The financing involved a ground lease from the District of Columbia, a tax-exempt bond financing transaction and a New Market Tax Credit financing transaction.
  • Representing DLC Management Corporation in connection with a wide array of real estate transactions.
  • Representing the owners of Washington Sports & Entertainment Limited Partnership in connection with the sale of all of its interests in the Washington Capitals, the Washington Mystics, the Washington Wizards, Verizon Center, and the Washington-Baltimore Ticketmaster franchise to Monumental Sports & Entertainment.

Publications, Presentations & Recognitions

  • Tommy has been recognized as a top real estate lawyer by Chambers USA, 2019-2024, Legal 500 US, 2017-2024, and Washingtonian Magazine, 1998- 2022.
  • In 2023, Tommy was recognized by Connect CRE’s Annual Lawyers in Real Estate Awards for Washington, DC.
  • In 2013, Tommy was featured in The National Law Journal’s “District’s Deal Makers of the Year” report. He is also a frequent speaker at commercial real estate industry events.
  • In May of 2007, Bisnow (formerly Bisnow on Business) named Tommy one of the top 35 rising stars under the age of 35 in the Washington, DC commercial real estate industry.
  • Practices
  • Bar & Court Admissions
    • District of Columbia Bar
    • Maryland Bar
  • Education
    Georgetown University Law Center, JD, cum laude, 1997
    Williams College, BS, cum laude, 1994



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