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When the biggest mega real estate deals transpire in Southwest Florida, Michael McCumber is often the man making it happen. He’s the one who smashed the real estate sales record in 2025 with the $225 million deal on a legacy compound spanning 15.1 acres and 800 feet of Gulf frontage. It was the largest residential transaction in Florida’s history and one of the largest residential transactions ever in the U.S.

In 2014, 2015 and 2018 he was also at the helm putting together the sales of the highest priced homes in Collier County. The owner of The McCumber Group at Waterfront Realty Group pairs the perfect sellers and buyers together through discretion, long time contacts, decades of experience and very personalized service.

The beginnings

Michael McCumber moved to Naples from Fort Lauderdale to attend Naples High School. After graduating, he went to a marine engineering school in Key West. Then he returned to Naples and started Marine Management Yacht Services in 1984. That’s where he got his first taste of spending time with the ultra-wealthy. He learned about hard work, trust, discretion and the art of giving high quality personalized service. McCumber also started learning a bit about real estate.

Mike McCumber. -COURTESY PHOTO

“All the boats would leave every May to go up north or into storage, and I would have to let a lot of my employees go for the summer,” McCumber explained. “So, I started buying homes in the spring and my employees helped me renovate them all summer long, so everybody had a job, and when October came along, they would go back to their jobs and I would start renting the houses.”

His boat customers were impressed by this hard working, forward thinking, young entrepreneur.

“One of my clients did not get along with many of the Realtors out there, and he asked me to get my real estate license. He trusted me to find and sell them homes,” McCumber recalled.

In 1997 he got his real estate license and began his second career with the Premier Properties, the Lutgert Companies while still running his marine management business.

He used his experience of traveling with wealthy clients and making good contacts to work his way up in the real estate world. In the early 2000s, he made the areas first deal that was more than $10 million.

“A client in Port Royal asked me to list his property,” McCumber began. “Everyone thought it would be a tear down. He asked an exorbitant amount at that time; $10 million. Nobody had ever broke $10 million, and I was not afraid to ask for it and the buyer thought it was one of the most special lots and he was willing to pay $10 million.”

In 2008, he started Gulf Coast International Properties.

“We started it at the very bottom of the crash,” McCumber said. “We figured if everybody was at the bottom, we could only go up from there. The very large companies were buying everybody and consolidating. We only wanted to work in the boutique business, so we started Gulf Coast International Properties. And we became one of the top boutique real estate places.”

Mike McCumber 2200 Gorden Drive. -COURTESY PHOTO

Last year when he felt that Gulf Coast International Properties was getting too big for him, he sold that company to his partner and bought Waterfront Realty Group. Waterfront, that began in 1986, is one of the oldest boutique firms.

“The company (Gulf Coast International Properties) grew and grew, and I continued to have less and less time to focus on serving my clients one on one, so I decided to buy the boutique firm to go back to a small group,” McCumber explained. “I wanted to spend more quality time focusing on my high-end clients.”

Challenges and rewards

It can be glamorous, exciting and profitable, but it is also a career filled with incredible challenges. Many of his clients don’t want their home listed on the internet. They don’t want a For Sale sign out front. Instead, they look for a discreet sale.

“A wealthy client will say ‘I want you to list my house for more than it is worth, no signs, no advertising and certified buyers only’.” McCumber described. “That is standard in the high-end business, which makes life a little more complicated.”

It is all about word of mouth, socializing with the right people and securing trust.

“When one of them has a good experience with you, you become the name that gets passed around at the dinner table or out on the dock. That’s how relationships compound over decades,” he explained. “Once you are in the circle of trust, most of the clients will ask you to come to their summer homes or their winter homes and help them with things. I spent years captaining large private yachts for some incredibly successful people in Port Royal, and when you’re out there with someone for weeks at a time, you build a real bond. Most of my experience in finding high end clients are from word of mouth, through the inner circles, making great relationships with high end real estate agents around the world and doing referral business. My bread and butter in the business has always been having a close relationship with builders and architects and never losing sight of where I started. It takes years of hard work and trust by the clients to work on these very large deals.”

It also takes patience. When a client asked him to secure a large piece of land near the heart of Naples where they could have a horse and create an organic farm, McCumber spent years piecing together the purchase of numerous adjacent properties to create a place big enough to meet his client’s goal.

The job also requires a plethora of deep-pocketed contacts.

“There was a very small market of people who were capable of purchasing that kind of property,” McCumber said about the $225 million legacy land. “It was not just the $225 million, it was what they would do with the property, and the request from the seller was to find someone who would keep the property intact and not chop it up into individual pieces. We realized it was going to be a very difficult task to find a qualified buyer and come to a closing.”

McCumber reached out to contacts at the Naples Winter Wine Festival and to some high-end agents in the Palm Beach market. Finally, a representative from the buyer’s family reached out to McCumber to see if they could reach a deal.

It doesn’t get any easier once a buyer is found. The $225 million deal took a year to complete. It entailed using 15 attorneys from multiple countries, multiple corporations and private family trusts.

“Every party has their own counsel, their own timeline, their own concerns and your job is to hold the whole thing together without letting the deal collapse,” he explained. “The logistics alone are staggering; coordinating across time zones, legal jurisdictions, currency structures and personalities, and unlike a traditional transaction, there’s not a real playbook for a $100 million plus deal because each one is completely unique in its structure and complexity. You also have to manage the emotional side of it. This is a property the owners have owned for decades and it carries real sentimental weight. Understanding and honoring that is just as important as getting the numbers right. You have to be calm, organized and intentional, because one wrong move or one impatient phone call can unravel months of work. Some of my biggest motivators and why I am at the top of the high end is that I have always been addicted to the art of the deal.”

He never met the new owners and only knows that they are from outside of the United States. That prompted him to help the buyer not only make a deal on the home, but make plans for the future of the property.

“We assembled a 5-star team that did everything from FEMA, coastal control landscape architecture, architect, builders and attorneys,” McCumber explained. “We suggested to the buyer that we have the best team in Southwest Florida and if they were willing to hire and interview the entire team, that my seller would be more motivated to negotiate a settlement.”

That didn’t stop the obstacles from coming.

“The deal went south multiple times in a 10-month period,” McCumber admitted. “There were three hurricanes and the elections. The world was against us. Every time we put the deal together, the buyers disappeared because we had a hurricane and another hurricane and then when the elections happened, they immediately vanished, but after the outcome they felt it was a more inviting political climate for them to make a move.”

Finally, after a year, the deal finally closed. McCumber attributes that success and others to the relationships that he builds. He does all this without the fanfare and without the glory.

“Discretion isn’t optional,” he stressed. “It’s a requirement. The buyers and sellers don’t want their names in the paper. They don’t want competitors or the public knowing their moves, and they don’t want the attention that comes with a nine-figure transaction. My job is to make sure the deal gets done quietly, cleanly and with zero leaks. The moment someone feels like their privacy isn’t protected, you lose the relationship and you don’t get a second chance with these people.”

Yet even without the glory, McCumber says the sale was his favorite deal.

“To represent the largest residential sale in Naples’ history, and the second in the country as the only broker involved, that’s something that very rarely happens anywhere in the world,” he exclaimed. “And the fact that we did it as a small boutique team, without a massive corporate machine behind us, made it that more meaningful.”

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The future

McCumber sees a future of more massive deals on the horizon.

“I believe that the beach properties and all waterfront properties will continue to increase,” he predicted.

He said the political climate coupled with buyers now not only coming from the Midwest, but from California and New York, has helped make property more valuable. The three legacy properties: The Naples Beach Club, the Port Royal Club and the Old Naples Hotel and all being fully renovated, and will help lure luxury buyers to the area.

“So many wealthy people were visiting Naples,” he said. “Naples was put on the world map during covid. There was an influx of clients coming from very restrictive places. After the elections, due to the political climates around the United States, Florida has become the landing zone for all the ultra-wealthy. It is a safe haven. Naples is still the small town, white beaches, shops and restaurants and 100 plus golf courses, and a private jet port within 10 minutes away. Naples is in a remarkable position. We’re seeing sustained demand from buyers who are relocating from high-tax states, international buyers who see South Florida as a stable place to park wealth and a waterfront inventory that simply cannot be replicated. We’re at a point in Naples’ growth where the city is maturing into a world-class destination.”

McCumber is also looking at the future of his firm, by mentoring the next generation of mega agents.

He appointed Realtor and technology whiz Anthony Caraballo as a partner and broker associate. He said the pairing of old school and new school real estate philosophies will keep his company on top.

“I spent my life shaking hands and being very personable with my clients,” McCumber described. “The young agents coming aboard, trying to crawl up the ladder, they spend their life on their phones and their tablets and have very little one on one personal skills, so I felt we had an opportunity to blend our history of shaking hands to mix with the new technology. When things change with technology and you have no idea, and you don’t want to go back and start over learning, hire somebody who does.”

Anthony Caraballo. -COURTESY PHOTO

Caraballo graduated from the University of Miami where he studied production, motion pictures and media

“That is what I bring to the table; how to market and find today’s buyer,” Caraballo said. “He is great at the old school handshake, and I combine that with the marketing and technology and cutting edge to keep us competitive.”

“We realized that a lot of the agents out there had zero people skills and had no idea how to engage with high end buyers,” McCumber added. “We decided to spend a lot of time training the next generation. If you want to work in the high end you need to be able to shake hands and look someone in the eyes. AI has its place in this business. We embrace the technology to reach out around the word to reach high end-clientele, but once we get the engagement, it is now time to build the trust with the clients whether it is the sellers or the buyers. Our relationships with our clients have always been first and foremost.”

Check back to Florida Weekly for more in-depth articles on the real estate professionals shaping the Naples area.