Old Naples has seen its biggest home resale of the year.
A Gulf-front estate in the neighborhood fetched $27 million.
While the newer home went for less than its original listing price of $39 million, the sale still ranks as one of the highest residential deals of 2026 in Naples.
According to the selling agents, it’s the fourth-highest existing home sale — or resale — of the year in the city, trailing three others in neighboring Port Royal, recognized as one of the most elite and exclusive enclaves in the United States.
Located at 26 Second Ave. S., the estate, completed in 2025, was designed by Humphrey-Rosal Architects and built by D. Garrett Construction. It includes 8,770 square feet of living space, sitting on a more than half-acre lot, with more than 120 feet of Gulf frontage.
Delivered as a decorator-ready residence, it provided the buyer with the opportunity to add personal touches.
The residence includes a rooftop deck that spans more than 5,000 square feet with glass railings and provides panoramic views of the Gulf. A private elevator services all levels of the residence, including the deck.
Additional features include covered terraces overlooking the beach, a pool and spa, an outdoor shower, a whole-house water filtration system, a generator, electric screens and shutters and garage parking for at least six vehicles.
The seller was represented by Jordan Delaney and Ryan Frost of Premier Sotheby’s International Realty’s Village office in Naples.
Eric Cady, a broker associate with Shore Line Realty & Associates in Cape Coral, represented the buyer.
County records show the property was previously sold as vacant land for $11.5 million.
Demand for rare real estate remains strong
The much-improved property, which hit the market in January 2025, sold in less than 18 months, which the listing agents described as “remarkable,” especially considering it happened outside of the busy season.
“This sale reinforces the enduring value of truly exceptional real estate and the continued strength of our local market. It reflects sustained confidence among affluent buyers and a continued demand for Naples’ most coveted Gulf-front addresses,” Delaney said. Properties of this caliber are exceedingly rare, and when they become available, they continue to attract significant interest from discerning buyers seeking not only a lifestyle, but also a legacy asset that can be enjoyed for generations.”
Today’s ultra-luxury buyers are well informed and prepared to act decisively when an opportunity like this one presents itself, he said.
“It is very common for a client to hop on a jet and fly in just for an afternoon, as buyers who know Naples well understand the scarcity of premier waterfront properties,” Delaney said.
Even in the depths of summer, demand for exceptional properties in Naples remains “remarkably resilient,” he said.
“The combination of lifestyle, wealth migration, limited waterfront inventory and long-term desirability continues to support strong values at the top end of the market,” Delaney said.
More big residential sales in Naples
Earlier this year, a Gulf-front triple residential lot traded for more than $27 million in Old Naples, but it did not include a home.
So far this year, the biggest sale of an existing home in Naples is $55 million. The sale happened in January, involving a sprawling waterfront estate at 4296 Cutlass Lane in Port Royal, with six bedrooms and 13 bathrooms.
The $55 million sale didn’t come close to the highest ones of 2025.
Last year, Naples entrepreneur and billionaire David Hoffman bought a newly built estate in Port Royal for $85 million. It set a new all-time record for a residential sale in Naples.
The record didn’t last long, however, overshadowed by the sale of a larger legacy compound in Port Royal that fetched $225 million in the same month.
Laura Layden is a senior business and government reporter. Reach her by email at laura.layden@naplesnews.com.
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This article originally appeared on Naples Daily News: Gulf-front home in Old Naples fetches $27 million
Reporting by Laura Layden, Fort Myers News-Press & Naples Daily News / Naples Daily News
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By Laura Layden, Fort Myers News-Press & Naples Daily News | USA TODAY Network
