Trey R. Milam


Trey R. Milam


Phone: 207.253.0543 Fax: 207.772.3627 Email:

84 Marginal Way, Suite 600 Portland , ME 04101-2480

Assistant: Beth Hollmann Email:


Trey Milam is an attorney with the Real Estate Practice Group at Drummond Woodsum. Trey works with a wide range of clients, including entrepreneurs, organizations, and institutional lenders. He understands that no two transactions are alike; and enjoys providing creative solutions to unique problems while crafting deal structures that meet his clients’ needs and goals. Additionally, Trey’s familiarity with, and knowledge of, bankruptcy law has heightened his understanding of how transactions can fall apart, which he uses to his advantage when putting them together. Having represented both debtors and creditors in debt restructuring matters, Trey draws on this experience to thoroughly analyze each transaction with an eye toward staging the best possible outcome in a variety of scenarios. He is most passionate about providing effective and efficient services – whether constructing deals, guiding negotiations with adverse parties, or explaining a niche area of property law, Trey draws enormous satisfaction from protecting the interests of his clients.

Trey’s background in nonprofit conservation also gives him a unique and informed perspective when assisting clients with land use and conservation matters. A lifelong outdoor enthusiast, he appreciates the opportunity to work with clients to preserve Maine’s treasured forests, open spaces, and working farmland. Similarly, his experience representing commercial borrowers and lenders from commitment letters to closings, as well as successfully defending against and pursuing foreclosure judgments and auctions, gives Trey a unique set of tools to deploy in any circumstance.

Trey pursued his Juris Doctor at the University of Maine School of Law, where he graduated cum laude and received the University of Maine School of Law Commercial Law Award. He received a Bachelor of Arts degree in Environmental Studies from Hamilton College. Trey lives in North Yarmouth with his wife, dog, and three cats, and in his spare time enjoys hiking, skiing, camping, cooking, and riding and wrenching on bicycles.


University of Maine School of Law, J.D., cum laude

Hamilton College, B.A.


University of Maine School of Law Commercial Law Award, 2019


Maine State Bar Association

Community/Public Service

Practice Areas