Melissa Caldwell

Board of Directors Member at Caldwell Trust Company

Melissa Caldwell is a proud Florida native with deep roots in Sarasota, a place she now calls home for life. Originally from West Palm Beach, her Sarasota journey began in 2001 when she visited to participate in triathlons at the invitation of friends. It wasn’t long before she fell in love with the area—and with her future husband, R.G. “Kelly” Caldwell, Jr.

Melissa and Kelly married in 2004 and made Sarasota her permanent home. With a background in sports marketing, Melissa swiftly transitioned to real estate, obtaining her license soon after moving. A pivotal introduction by Kelly’s mother to real estate veteran Linda Bradway opened doors, and Melissa has built a successful 20-year real estate career with Linda playing a key role in her continued growth and success.

As they started their family, Melissa also became increasingly involved with Caldwell Trust Company, the family business founded by Kelly’s father, Roland Caldwell, in 1993. By 2023, as the company celebrated its 30th anniversary, Melissa took her involvement to a new level, joining the board of directors and working closely with Kelly, who has been President and CEO since Roland’s retirement in 2007.

“I’ve always been engaged with Caldwell Trust Company as a spouse, but now I wanted to dive deeper into the operations and contribute in a meaningful way,” says Melissa.

Melissa’s connection with Caldwell Trust Company goes beyond family. She shares a strong personal bond with Wendy Fishman, CTFA, Executive Vice President and Senior Trust Officer. Wendy’s support became invaluable to Melissa during a particularly difficult time after her father passed away. Wendy’s care and attention, both professionally and personally, helped Melissa, her mother and siblings navigate the complexities of that period, deepening their lasting relationship built on trust and compassion. Wendy’s exceptional service solidified the Caldwell Trust Company’s commitment to treating clients like family, ensuring they feel supported in every aspect of their financial journey.

Caldwell Trust Company has grown into a leading wealth management firm in Venice, with a significant presence across Sarasota and the central Gulf Coast. Kelly Caldwell shares, “Melissa brings a unique combination of real estate and  finance expertise and a deep commitment to community engagement, which enhances our board’s strategic vision. Her insight and dedication will be invaluable as we continue to serve our clients and expand our impact in the region.”

Outside her roles as a Global Real Estate Advisor with Premier Sotheby’s International Realty and board member of Caldwell Trust Company, Melissa is dedicated to local philanthropy. She’s heavily involved with the United Way of South Sarasota County and helps organize the annual Celebrities and Heroes Softball Game and Concert at Cool Today Park, an event benefiting local veterans and first responders.

“I’ve always loved sports and the outdoors,” says Melissa. “Cool Today Park is such a gem, and the Atlanta Braves have been fantastic partners. We bring in a country music star to cap off the day with a concert, all for a great cause.” 

In addition to her charitable work, Melissa supports the Boys and Girls Club of Sarasota, an organization close to her heart as her three sons were involved with it during their youth.

A passionate and talented tennis player, Melissa captains the “No Drama Mamas,” a women’s 4.0 tennis team out of Payne Park Tennis Center. Her team recently clinched the championship for the Sarasota region in the USTA league.

For Melissa and Kelly, Sarasota is their forever home. Whether they’re exploring the waters of the Gulf, or taking Kelly’s airplane for a quick breakfast to St. Pete or Arcadia, adventure is always on the horizon.

Text by Tom Reese | Photo by Nancy Guth

Sarasota:
27 South Orange Avenue 
Sarasota, Florida 34236
941-841-4579

Venice:
1400 Center Road
Venice, Florida 34292
941-220-0293
ctrust.com