Winfield was born in Philadelphia, Pennsylvania in 1962. Winfield graduated from the University of South Carolina in 1984 with a Bachelor of Arts degree. While attending USC he was a member of the Kappa Alpha fraternity. Winfield received his Juris Doctor degree from the University of South Carolina School of Law in 1988. While attending law school he clerked for the law firm of Robinson, McFadden & Moore.
Winfield joined the Bellamy Law Firm immediately following graduation in 1988. Winfield is part of the Myrtle Beach real estate lawyers team at Bellamy Law Firm, and advises clients in all matters of real estate law, including land acquisition and planning, preparation of master deeds, declarations of covenants and restrictions, and real estate closings. Winfield also advises clients in business and financing transactions. Winfield is a member of the Horry County and South Carolina Bar Associations.
Winfield resides in Murrells Inlet with his wife, Robin, and their daughter. When not practicing law, Winfield is an avid fisherman and particularly enjoys fly fishing.