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About Dean Matthews

Dean

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Meet Dean

A former award-winning financial advisor, Dean Matthews managed portfolios exceeding $100 million at Raymond James & Associates and Bank of America Investment Services before transitioning into real estate over 14 years ago. He began his real estate journey as an investor, acquiring, renovating, and reselling homes—gaining hands-on experience and a deep understanding of the market from the ground up.
 
Today, Dean specializes in luxury real estate across Jupiter, Palm Beach Gardens, North Palm Beach, and Singer Island. He leverages his extensive background in finance, sales, marketing, and digital media to deliver a sophisticated and strategic approach tailored to each client. His passion for real estate and the Florida lifestyle is evident in the personalized service and local insight he brings to every transaction.
 
A longtime Jupiter resident, Dean offers clients an insider’s perspective on the area's history, neighborhoods, and waterfront opportunities. Alongside his wife and business partner Heather—his teammate of over 25 years—Dean offers private tours of the area, including complimentary boat excursions to showcase waterfront homes from the most compelling vantage point.
 
Dean holds a B.A. in Business and Finance from Florida Atlantic University. In his free time, he enjoys boating, golf, and basketball, and values time spent with Heather and their three children.

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Whether you find Gary jogging past your street, walking his dogs Posey and Potter, or heading to dinner on a golf cart with his family, he lives the lifestyle he represents — and helps every client feel like they belong the moment they arrive.

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