Caitlin Cunningham

Real Estate & Land Use


North Carolina
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Caitlin joined Scale in 2024 following a 13-year career with the federal government, where she worked in both real estate program management and transactions, with a focus on commercial leasing, land acquisition/disposal, and land use issues. In this capacity, Caitlin gained a broad range of experience in multiple business lines, including corporate governance, commercial contracts, and partnerships; federal regulations; medical and agricultural research; healthcare; cemetery and memorial properties; and agricultural grants and programs. She also has experience working with homeowners’ associations and real estate brokerages in navigating compliance and governance issues. 

Prior to her government career, and throughout law school, Caitlin worked as a paralegal with a focus on commercial real estate transactions and financing, corporate governance, and trusts & estates matters. This experience honed a keen attention to detail and pragmatic approach that Caitlin brings to her practice today. 

Representative transactions:

  • Subcontractor to a federal agency to analyze the community, economic, environmental, and social impacts associated with the conveyance of 10 former federal properties to non-federal entities. The studies included land use analysis, title and survey review, site visits and interviews with community stakeholders, review of environmental studies and state data, and the drafting of a final report to present agency leadership.
  • Led a multi-year project to unravel the land records of a Medical Center and Cemetery properties, which date back to 1826, and to acquire additional land for expansion of the cemetery. This project involved the use of licenses and permits, acquisition and disposition of easements, working with the County Parks Department to negotiate a property transfer, and reviewing extensive title and survey documentation.
  • Acquired multiple parcels of land and negotiated a Memorandum of Agreement with natural gas company to support major construction project for National Cemetery expansion.  Project encompassed the acquisition of 137 acres of land and involved complex negotiations with two neighboring landowners, a natural gas company, and BLM, while keeping multiple Congressional offices up-to-date on progress. Project also involved significant archeological preservation efforts in partnership with local Native American groups as well as application of the Uniform Relocation Assistance and Real Property Acquisition Policies for acquisition of land. 
  • Led a matrix team of subject-matter experts in the transfer of 600+ acres of land on the San Francisco Bay, which included preservation and mitigation of endangered species habitat, partnership with several area conservation groups, re-negotiation of land use licenses, and agreements with the local government as to utility and street infrastructure. Project also included negotiations with the Department of Defense on mitigation and disposal of hazardous materials on-site. 
  • Conducted competitive procurement and lease negotiation for a 42,000 SF medical research and vivarium facility in San Francisco, and 50,000+ SF healthcare facilities in California, North Carolina, Texas, Louisiana, and Montana.
  • Drafted language that is now Federal Law that expands VA’s ability to acquire leased space directly from academic affiliates, state and local governments, and non-profits for the purpose of providing healthcare resources to Veterans.
  • Supported programs in USDA’s Office of Urban Agriculture & Innovative Production and the Natural Resources Conservation Service, including roles in standing up the People’s Garden Initiative and the nationwide push to encourage sustainable and innovative farming practices in urban areas. Played a key role in the establishment of 17 first-of-their-kind urban service centers to provide financial and technical assistance to farmers in non-traditional locations.

Areas of Expertise

Real Estate Transactions

Land Use Issues

Corporate Governance and Transactions

Commercial Leasing

Government Leasing, Programs, Regulations, and Contracts

Prior Associations

U.S. Department of Agriculture

U.S. Department of Veterans Affairs

Ellenoff Grossman & Schole LLP

Potts-Dupree, Difede & Hawkins, Chtd.

Areas of Expertise

Federal Real Estate
Land Use
Government Contracts

Prior Associations

U.S. Department of Veterans Affairs
Ellenoff Grossman & Schole LLP
Potts-Dupre, Difede & Hawkins, Chtd.


The George Washington University
Brooklyn Law School
Georgetown University
St. Paul’s School

Bar Admission

New Jersey

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