Broker gets creative to sell $295 million Naples compound

Four months after one of the most expensive residential properties in the U.S. was put up for sale in Naples, the broker looking to land the buyers — and the commission that comes with it — is trying something new.

Dawn McKenna, who runs Coldwell Banker Realty’s Dawn McKenna Group, has turned to a Naples architect to create renderings of what the property could look like in order to give potential buyers an opportunity to imagine themselves living in the space.

The renderings show a 35,000-square-foot beach house (mansion?) as well as a second home, this one 22,0000 square feet and on the bay, with options for a private 3-hole golf course, two gated, but separate entries, a pickleball court, beach cabana with fully equipped summer kitchen, separate pool and a variety of fitness and water activity options.

The property is a 9-acre waterfront compound named Gordon Pointe in Naples’ Port Royal neighborhood. It currently has a 22,800-square foot home on it with six bedrooms, 20 full bathrooms and four half baths. It sits on 1,665 feet of water frontage — 728 feet beachfront and 927 feet bayfront — and has a yacht basin and T dock.

The asking price: $295 million.

“Ours is, I would argue, the apex of property available in America,” McKenna says.

“It’s very rare. In fact, I don’t know of another property that you can have a 231-foot yacht basin, you can have your own private beach, be in the state of Florida with no state income tax, have great weather, have this almost private island — I want to say peninsula, let’s not call it an island, let’s call it a peninsula — be attached by land and to be able to jog to town, grab a bite to eat, throw yourself on a golf cart and go grab dinner.

“It’s a very, very unique lifestyle that this property lends itself to.”

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Given how unique the property is, McKenna says the idea for the renderings was to show a potential buyer what could be done with it, how they can put their personal touch on the compound.

“The soup du jour right now for an ultra-wealthy person, family, is to have their own island, to have something rare,” says McKenna. “And when I say rare, I mean really rare. Like a one of a kind, the one and the only.”

But selling something like Gordon Pointe isn’t easy. There are only so many buyers in the world who can afford it. And it’s not like you can put up signs along the road for a Saturday open house in the hope a buyer swings by.

Home alone

McKenna, 55, is based in Illinois and has several offices in the state, including Chicago. She also has teams operating in Naples, New Buffalo, Michigan; Park City, Utah; and Lake Geneva, Wisconsin.

A native of Chicago’s south side and from modest means, she founded her team in 2016 and in 2023 saw more than $590 million in transactions, according to Coldwell Banker.

A big part of the reason for McKenna and her team’s success is the approach they take when marketing properties, she says.

When the Gordon Pointe house in Naples went on the market, it was featured in The Wall Street Journal and from there the buzz grew. Stories about the property appeared in about 400 news publications in 14 countries, with major interest in Canada, Europe and Asia along with the U.S. 

One of her most recent listings was the Illinois house featured in the classic Christmas movie “Home Alone” which also drew global attention.

McKenna says she and her team used a similar approach on that house as they did when first listing the Gordon Pointe property.

“We strategized,” she says. “We didn’t just press the button and put it on” the market.

Work included understanding advantages of the Winnetka, Illinois, house’s notoriety while balancing the realities that someone was going to live in it.

That meant highlighting it was near a lake, it was in town and looking at the fact that the house behind it was under contract — tasks any Realtor would do when selling a house.

But this was not an ordinary house. It is one of the most Googled houses in the world (it averages 70,000 searches per month worldwide according to the tech publication The Street) and the owners have been asked hundreds of times to use it in ads, so there is the possibility that there would be a return on investment for the buyer.

The house went on the market the Friday of Memorial Day weekend this year. And that was no accident. Neither was the decision to not allow any showings until the following Tuesday. “We wanted people to take a minute, look at it, get excited about it and come in,” she says.

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McKenna says they launched a social media campaign on that Friday and gave the story to The Wall Street Journal. The listing, she says, got more than 940 million views globally and potential buyers flocked to it. “We showed it for two days straight, and then took off multiple offers.”

(The deal has not closed and Coldwell Banker says in a statement that “while we’re unable to discuss information about pending transactions, we are able to confirm an offer is now pending after less than one week on the market — and within days of showings.”)

 “The sellers were very happy with the way it all turned out,” McKenna adds.

“But it’s not for everybody. All these properties, you have to understand, are not always for everybody. But it’s our job to make everybody in the world actually pause for a minute and think what would be there and be intrigued by it.”

Future visions

McKenna is not alone in her efforts to sell the Gordon Pointe property in Naples.

She is working with The Leighton Candler Team of The Corcoran Group, which has offices in New York City, the Hamptons and South Florida, and Rory McMullen of Savills, a London-based real estate firm. This is in order to reach a larger, global clientele. (While broker-commission rates can be negotiated, at a 5.37% commission — the average in Florida in 2023 — a full-ask sale of $295 million would net a $15.84 million commission. It’s unclear what rate McKenna and the other brokers will receive.)

To date, McKenna says, they have been showing the property regularly and are getting significant positive feedback.

But, given the price point and the buyer pool, it’s a process that takes time.

McKenna, in an email following an interview, says “marketing a property like this is not for the faint of heart. It starts with a hefty budget but also significant resources, strategy and execution.” 

McKenna sat down with her head of development, Christine Lutz, early on, to see what could be done to create an experience in order for potential buyers to visualize what the property could be for them.

She then consulted friends and colleagues in Palm Beach, Miami and the British Virgin Islands to talk about what buyers for a property like Gordon Point look for, what they want, what their needs are and what makes them happy.

They also wrote down everything people said they looked at the property.

“I blended it up and then Christina and I came up with a recipe after we had had significant interest and significant buyers coming to the property,” McKenna says.

What they decided was people looking at a rarefied property like Gordon Pointe with a $295 million price point, want what they want.

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So McKenna and Lutz contacted Brad Palmer with Harrison Design, a national firm with an office in Naples to draw renderings. He has experience with family compounds.

The idea is for the renderings is to help potential buyers visualize the possibilities of the compound, she says. Parker, in a statement, says the placement of main house in the drawings captures the sunset and has views of the entire peninsula.

“I thought,” McKenna says, “we would create a little bit of a shell, if you will, on what life could look like there. That’s what the mastermind was behind creating this, these two beautiful homes and how the whole thing would work from a lifestyle standpoint.”

She then adds a moment later, “This was very strategic. It was it was the definition of the perfect blend of art and science.”