A Florida penthouse listed for $37.5 million in Naples. Is it the city's most expensive?

A penthouse in Naples, Florida has quietly listed for $37.5 million.
That makes it the most expensive resale condo on the market in the city.
There is at least one new penthouse going for more, according to the Southwest Florida Multiple Listing Service (MLS). Its price tag: $45 million (for delivery in 2027).
New condos usually don't appear on the MLS.
Here's more to know about the renovated move-in ready offering, which could set a new benchmark for its tower and the Naples resale condo market:
Where is it located?
It's Penthouse 2 at The Regent, a 24-story tower in the Park Shore neighborhood. The tower offers panoramic views of the Gulf of Mexico and Venetian Bay, sitting at 4101 Gulf Shore Boulevard North. In total, the building has 37 condos.
When was it built?
The tower was delivered by The Lutgert Cos. in 2002, but Penthouse 2 has been "completely reimagined," creating a residence that is "a sanctuary of elegance and comfort, perfectly tailored for modern living," according to the listing.
How big is it?
The home stretches a little over 12,000 square feet under air. At The Regent, there are five penthouses, on the top five floors, with each condo taking up an entire floor.
What does it offer?
It includes four bedrooms (all suites), with a total of five full and two half bathrooms. Other features: An expansive great room, a wet bar, two offices, a media room, a cabana room, a game room, and space for exercising.
What else makes it special?
The listing describes the penthouse as chic, but informal, embodying "a harmonious blend of interior design ingenuity and refined luxury," after a reimagination that involved a collaboration between the renowned Suzanne Lovell Inc., one of Architectural Digest’s top 100 international interior design firms, based in Chicago, and master craftsmen from Kurtz Homes and Thomas Riley Artisans’ Guild (two local companies). The interior design "embraces texture and artistry, from light wood flooring and shiplap walls to rope and woven leather accents."
Who are the listing agents?
Thomas Campbell and Richard Prebish, who pride themselves on putting "confidentiality before any other consideration," and have a general policy of not commenting on their sales, or listings, to protect the privacy of their clients. They've sold more than $1.5 billion of real estate since 2020, according to their page on the William Raveis website.
More about the condo and the market
Property records show the penthouse last sold for $14 million in 2020. The current owners are listed as William and Kristin Fenech. A Google search reveals he made his money in the boating and RV industries, as a founder of Grand Design RV and Barletta Boats (both purchased by Winnebago Industries – at different times).
Since last year, a few penthouses have come to the market at eye-popping prices in Naples. Penthouse 3 at The Regent is also for sale after a remodel, with a price tag of $29.5 million. It hit the MLS last March, raising eyebrows, as a then unheard-of asking price in the tower.
Last February, a penthouse in The Seasons at Naples Cay, known for short as PH20, listed for $32.5 million, after a redesign, making local headlines as the most expensive condo resale on the market at the time.
That penthouse is now offered at a reduced price of $27.9 million. It boasts 16,803 total square feet, with 11,960 of that space indoors, and 4,843 of it on outdoor terraces. There are five bedrooms and seven bathrooms.
Located at 81 Seagate Drive, Naples Cay has been described as "an intimate experience," with a total of 43 condos. The 22-story, gated beachfront high-rise tower, offering views of the Gulf of Mexico and Outer Clam Bay, was completed in 2002, the same year as The Regent, by a different developer.
The most expensive penthouse listed on the Sunshine Multiple Listing Service in Naples is one that is not yet built. It's at the Rosewood Residences, a club-style community that's still under construction on Gulf Shore Boulevard North, with an expected delivery in 2027.
The Rosewood Residences will have two buildings, each with six floors of ultra-luxury condos, sitting over one level of parking. There will be 42 homes in all, with prices ranging from $12.75 million to $45 million (for the most expensive penthouse).
The exclusive community is replacing the old Mansion House on 5 acres of beachfront property, overlooking the Gulf of Mexico. It will be managed by Rosewood Hotels and Resorts, a leader in ultra-luxury hospitality.
According to the listing, the priciest penthouse includes six bedrooms, with six full and two half bathrooms, spanning 9,673 square feet.
The next most-expensive penthouse, priced at $30 million, has a pending contract (for an undisclosed price).
Seven months before Hurricane Ian, the Ronto Group announced its purchase of the property, at 1601 Gulf Shore Blvd. N., in partnership with Wheelock Street Capital, for redevelopment.
Ian has sped up redevelopment along a 1.3 mile stretch of Gulf Shore Boulevard North, now dubbed the "Miracle Mile" for its endurance and promise after the storm left it looking like a war zone.
"In the history of the MLS, there have been four condos listed above $30 million," said Denny Grimes, a long-time Realtor and local real estate market expert with Keller Williams Realty.
Last year, the highest price paid for a penthouse in the Naples area was $17.5 million, he said. Spanning 5,202 square feet, it's at Mystique, in Pelican Bay.
Pelican Bay, an upscale master planned golf and beach community in North Naples, is known for its posh homes and high-rises. The last tower, called Epique, is currently under construction. Described as a sister to the Mystique, it will feature 18 floors, with 68 condominiums, including four penthouses, with pricing not yet advertised.