Business Leaders Return to Community Foundation Board

The Community Foundation of the Florida Keys is pleased to announce that estate attorney Bobby Highsmith and real estate investor Ken Silverman have been elected to its Board of Governors. The Board is responsible for the organization’s efforts countywide including managing over 180 charitable funds totaling over $25 million, making grants over $2 million annually to support Florida Keys nonprofits.

Silverman returns to the Community Foundation’s Board of Governors after serving from 2015 to 2021, when he was Treasurer and served on the Finance, Investment and Development committees. This is Highsmith’s third time on the Community Foundation board. He was board chair for two of the years during his first term from 2000 through 2005, then came back to serve on the board again from 2014-2017.

Bobby Highsmith is managing partner of Highsmith & Van Loon and has achieved a successful 30+ year career specializing in estate planning. He is the only Florida Keys attorney who is Board Certified in Wills, Trusts and Estates. Born and raised in Key West, Highsmith was valedictorian of Key West High School. He fulfilled his dream of starting on a Division 1 college football team at Duke University, which he attended on a full athletic scholarship.  He went on to graduate from University of Florida Law School. Highsmith was Chancellor of St. Paul’s Episcopal Church and has served on the boards of the Monroe County School District and the Tennessee Williams Theatre.

Ken Silverman is a graduate of the MIT Sloan School of Management with degrees in engineering and computer science. He retired to Key West in 2012 after a 30 + year career in the New York City residential real estate management and sales industry, concentrating in high end luxury housing, middle income investment properties, and assisted and regulated housing. In his retirement he manages Key West commercial properties including the 400 block of Duval Street and the Overseas Market Shopping Center anchored by Winn-Dixie. He and his wife Kate spend part of the year in Amagansett, New York.

Highsmith and Silverman join Community Foundation board members Will Langley (board chair), Jennifer McComb (president), Tom Swain (treasurer and finance chair), Jodi Weinhofer (secretary), Marian Buccafurni (investment and grants chair), Ron Burd (development and governance chair), Warren Leamard, Laura Lietaert, Heidi Morris, Larry Nolt, and Andrea Spottswood.

To learn about opportunities to serve on nonprofit boards in Monroe County, contact the Community Foundation of the Florida Keys at 305-292-1502 or

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