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Our Legacy

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A Story Rooted in Naples

The story of The McCumber Group begins decades ago, long before record-breaking sales and national recognition. It begins at the Port Royal Club, where a 15-year-old Michael McCumber worked as a maintenance man.

There, surrounded by the families who built Naples, Michael developed a reputation for hard work and trust. While still a teenager, he founded Marine Management Yacht Services, caring for the yachts of Port Royal’s most prominent residents. His role quickly grew from maintenance to serving as Captain, entrusted to guide Naples’ legacy families across Florida, the Caribbean, and beyond. For years, he safeguarded not just their vessels, but their families and their privacy.

From Yachts to Estates

The relationships built through this work became the foundation of Michael’s real estate career. His clients, unwilling to entrust their estates to anyone else, urged him to get his license. They knew he would bring the same integrity, discretion, and professionalism to real estate that he had brought to every voyage.

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A Career That Shaped Naples

When Michael was growing up, he could ride his dirt bike from Golden Gate to Bonita without passing a single home. By the 1990s, Naples had entered its historic boom. Michael joined The Lutgert Corporation, developers of many of the city’s landmark beachfront towers, gaining a front-row seat as Naples transformed into one of the most desirable real estate markets in Florida.

 During this time, Michael maintained a strong foothold in Port Royal, serving the same families he had known for decades. He later joined Premier Properties, still focusing on high-end waterfront sales. And when Premier was acquired by Sotheby’s, he co-founded Gulf Coast International Properties in the early 2000s. At a time when the market was at its lowest, Michael chose to step away from the national firms and create a boutique brokerage dedicated solely to servicing their clients' needs.

Michael went on to break record after record, becoming the first to surpass the $10M, $50M, and $200M thresholds. With over 40 years of experience serving Port Royal, he is recognized as the foremost expert on Naples’ beachfront and waterfront estates. His reputation is reinforced by longstanding local relationships with the region’s top architects, builders, and attorneys, built through decades of collaboration.

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Anthony Caraballo:
The Next Generation

After graduating from the University of Miami, Anthony Caraballo began his career at BCB Homes, one of the area’s most prominent luxury builders, where he gained firsthand experience in high-end construction. He earned his real estate license, and later his broker’s license and started building his career in sales.

Anthony joined Michael’s firm, where his creativity and marketing expertise quickly set him apart. With a mastery of digital marketing and social media, his content now reaches over 500,000 people each month, with millions of views and has amassed a following of 50,000+.

In 2023, Anthony and Michael officially partnered to form The McCumber Group, blending legacy expertise with next-generation innovation. Anthony assisted Michael in the record-breaking sale of 2200 Gordon Drive, one of the most significant residential transactions in U.S. history. His ability to capture attention at scale - while maintaining discretion - makes him a vital part of Naples’ future.

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Two Generations.
One Vision.

The McCumber Group is a small, boutique team dedicated to Naples’ most exclusive estates - specializing in Port Royal, beachfront, waterfront, and legacy properties. Michael’s legacy of trust and achievement pairs well with Anthony’s innovative, media-driven approach.

Together, they carry forward a tradition of professionalism and discretion while embracing the tools of the future. With an optimistic outlook on the future of Port Royal and its surrounding waterfront neighborhoods, The McCumber Group remains committed to representing Naples’ most extraordinary estates for generations to come.

Naples History

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Boutique Approach. White-Glove Experience.

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McCumber Group

Phone

(239) 300-8112

Email

[email protected]

Address

707 12th Ave S Naples FL 34102

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