Judge Keith Cary is a fourth generation native of Lee County, Florida. His family settled in Lee County at the turn of the twentieth century operating a sawmill and starting a cattle ranch. Judge Cary's family has been in the cattle business in Lee County for over eighty years.

Judge Cary attended the University of South Florida in Tampa and graduated with a degree in Business Administration. He was a member of the Phi Kappa Phi Honor Society. He obtained his law degree from the Cumberland School of Law of Samford University. After law school, Judge Cary returned to Lee County in 1978 and began his law practice as an Assistant State Attorney for the Twentieth Judicial Circuit. He then entered the private practice of law at the firm of Gerald, Cary & Duncan, where he practiced primarily in the areas of commercial real estate transactions and commercial litigation. In 1988 Judge Cary was elected as a Lee County Court Judge and served for 11 years, during which time he was a member of the Board of Directors of the Florida Conference of County Court Judges and served as Administrative Judge for County Court for six years.

In 1999 Judge Cary was appointed by Governor Jeb Bush to the position of Circuit Judge for the Twentieth Judicial Circuit. At the time of his appointment he transferred to become the Presiding Circuit Judge for Hendry and Glades Counties. He served in this position until 2004. Judge Cary served as the Chief Judge of the Twentieth Judicial Circuit from July 2007 through June 2011. Judge Cary was appointed by the Florida Supreme Court to serve as a member of the Florida Delphi Based Weighted Caseload Management Project (1999), the Supreme Court Work Group on Emergency Planning (2002), Supreme Court-Court Statistics and Workload Committee (2008 -Present) and the Florida Commission for Law Enforcement Accreditation (2007 -Present, Vice-Chairman 2010, Chairman 2011). He also served on the Executive Board of the Florida Conference of Circuit Judges (2007-2008).

Judge Cary is active in community events. He has served on the Board of Directors of the Fort Myers Kiwanis Club, Leadership Lee County (1998) and is currently Deputy Director of the Edison Festival Grand Parade of Light. He is married and has three sons.