Waterfront home in Old Naples that fetched $24.5 million headed for demolition

Laura Layden
Naples Daily News

After paying a near-record price for a waterfront home in Old Naples, the new owners plan to tear it down. 

While teardowns are nothing new for the wealthy set in Naples, this one will be a bit unusual, considering its price tag of $24.5 million.

That's the second-highest price ever paid for a home in Old Naples proper, said Craig Jones, a broker associate with Premier Sotheby's International Realty, who represented the sellers.

She described the anticipated demolition of the home — at 275 Gulf Shore Blvd. N. — as bittersweet.

"I like to see as many things as possible saved," said Jones, a former board member for the Naples Historical Society.

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While the charm of the 4,000-square-foot, one-story cottage, built in 1957, will be lost, its replacement promises to be more magnificent — and more resilient, given its location, just steps away from the Gulf of Mexico. 

"FEMA drives us all," Jones said.

The current FEMA, or Federal Emergency Management Agency, rules make a major renovation of the home unrealistic. The new owners would not only have to bring the home up to today's building standards, but elevate it, which are both costly and time-consuming propositions.

Today's FEMA rules are "good ones and that's what needs to happen here," Jones said.

She didn't reveal the names of the buyers or sellers, keeping them hush-hush, but public records shed more light on the deal.

Sold by a trust

This home recently sold for $24.5 million in Old Naples and it will be torn down.

Property records show the seller as a trust in the name of William Holekamp, a former executive for Enterprise-Rent-A-Car.

His trust purchased the property for $2.15 million in 1995, and the family owned and enjoyed it for decades.

"The last member of the family living there had passed away, and so it was time to move on," Jones said.

The deed lists the new owners as a Florida-based limited liability company that gets its name from the property's address.

State records show the company — 275 Gulf Shore Boulevard LLC — has two authorized representatives, John O'Donnell and Byron McMasters.

An internet search shows O'Donnell is the founder and CEO of inMusic, the parent of a family of music and audio equipment and technology brands. McMasters serves as the company's general counsel, according to its website.

Filippo Mastrocola, an agent with Premier Property Management, represented the buyers.

The quintessential cottage won't be the most expensive teardown in Naples: In 2018, a 10,825-square-foot mansion at 2500 Gordon Drive that last sold for $48.8 million got demolished, to make way for something fresh and different to suit its new owners.

Planning and permitting for the new estate in Old Naples could take a few years, so it's hard to know when "demo day" will arrive for it, Jones said.

The current home sits on 1.61 acres, with 189 feet of water frontage, which made the property highly attractive for its sweeping views of the gulf.

"It's rare for its size," Jones said, "It's rare for its location."

Top sale

This home recently sold for $24.5 million in Old Naples and it will be torn down.

While the multimillion-dollar sale might pale in comparison to the eye-popping ones seen in Port Royal over the past year, it still ranks among the top 12 residential sales in the city since the start of 2015, Jones said.

Last year,  Naples Realtor Bill Earls, with John R. Wood Properties, sold a stately family compound — at 2700 Gordon Drive — in Port Royal for $52 million, setting an all-time high record in the city, which stands.

He's handled other monster sales over the past year, attributing strong demand from affluent buyers in part to the coronavirus pandemic, which has made Naples an even sweeter "garden spot" for the uber-rich.

A few weeks ago, he sold a waterfront estate at 2050 Gordon Drive for $29.99 million. Spanning 5,393 square feet, it has four bedrooms, with four-and-a-half bathrooms. He considers it part of Old Naples, which would then make it the highest sale in the neighborhood.

"There is not any real magical dust in Port Royal property that doesn't exist across the line in another neighborhood. It's a Naples-driven thing," Earls said of buyer demand.

The home he just sold on Gordon Drive falls outside of what Jones and her team consider Old Naples, but it's not in Port Royal either.

While Old Naples is a "different animal" than Port Royal, it's still highly desirable, for many of the same reasons, including easy access to the beach, as well as downtown shopping, dining and entertainment, Jones said.

One of the big differences is a home in Old Naples doesn't come with the invitation or opportunity to join an exclusive country club, as is the case in Port Royal.

Although she didn't represent the purchasers of the Old Naples cottage destined for demolition, Jones worked closely with them to get the deal done.

"They were not unfamiliar with Naples," she said. "So they kind of came with an understanding of its value."

For the buyers, membership in the Port Royal Club wasn't important, Jones said.

Strong interest

The Old Naples home and its waterfront land, listed at $27 million, went for $2.5 million less than the asking price.

It was marketed as a dream spot to build a dream home, and it generated quite a bit of interest, bringing a total of 19 offers, which speaks to buyer demand, not just in the U.S., but internationally, Jones said.

This home recently sold for $24.5 million in Old Naples and it will be torn down.

Interested buyers saw the location as ideal, close to the hustle and bustle of the Fifth Avenue South and Third Street South shopping and dining districts — and not far from where the new Naples Beach Club development will be built.

The Naples Beach Club will include a Four Seasons Resort and high-class condos on both sides of Gulf Shore Boulevard, offering five-star services and amenities, much of which will be open and available to neighbors — and the public.

The cottage property hit the market in December 2020.

A sale would have likely happened sooner if there hadn't been an unexpected issue to resolve with the city over improvements to its stormwater management system, Jones said.

While all of the new drainage pipes are underground, an emergency generator for the new system sits above ground on adjacent property, so Jones and the former owners worked with the city to limit its visibility with a well-designed landscape plan, she said.

"It took time," Jones said. "But it was absolutely worth it." 

Whatever gets built on the rare property could be just a part-time — or vacation— home for the new owners.

"I'm not sure whether they would consider this as a primary residence, or not," Jones said. "People purchasing at this level typically have multiple homes."

Top Sales

Here's a look at the top home sales in Naples since Jan. 1, 2005: 

  • $24.5 million: 275 Gulf Shore Boulevard North. Neighborhood: Old Naples. Date sold: 2/16/2022. 
  • $24.5 million: 7613 Bay Colony Drive. Neighborhood: Pelican Bay. Date sold: 10/21/2015.
  • $28 million: 1832 Galleon Drive. Neighborhood: Port Royal. Date sold: 8/9/2019.
  • $29.99 million: 2050 Gordon Drive. Neighborhood: Gordon Drive Estates/Aqualane Shores. Date sold: 1/31/2022.
  • $31 million: 2976 Gordon Drive. Neighborhood: Gulfview Estates. Date sold: 7/13/2021.
  • $32 million: 2750 Gordon Drive. Neighborhood: Port Royal. Date sold: 12/21/2011.
  • $34.995 million: 3131 Fort Charles Drive. Neighborhood: Port Royal. Date sold: 1/26/2022.
  • $36 million: 2750 Gordon Drive. Neighborhood: Port Royal. Date sold: 1/28/2021.
  • $39 million: 3100 Gordon Drive. Neighborhood: Gulfview Estates. Date sold: 2/11/2021.
  • $48.8 million: 2500 Gordon Drive. Neighborhood: Port Royal. Date sold: 6/20/2018.
  • $49.5 million: 4540 Gordon Drive. Neighborhood: Port Royal. Date sold: 12/30/2021.
  • $52 million: 2700 Gordon Drive. Neighborhood: Port Royal. Date sold: 1/29/2021.

Source: Premier Sotheby's International Realty.