3565 Fort Charles Dr: Stunning $29.5 Million Waterfront Naples Home for Sale in Port Royal

Date of Publishing: March 26, 2025

Nestled within the prestigious enclave of Port Royal, 3565 Fort Charles Dr is a rare gem in the heart of Naples Real Estate. Currently offered at $29.5 million, this remarkable estate blends timeless elegance with sophisticated modernity, capturing the essence of luxurious waterfront living. Built in 2006 and recently renovated throughout, the 8,960-square-foot home sits on a 0.6-acre lot and features six bedrooms, eight bathrooms, and an expansive layout designed to take full advantage of serene views of Smuggler’s Bay. For those in search of a Naples home for sale, this property stands as a pinnacle of high-end living.

Front exterior view of 3565 Fort Charles Dr, a stunning waterfront Naples home for sale in Port Royal

A Legacy of Elegance and Craftsmanship

Perched on one and a half lots and framed by vibrant bougainvillea, the estate welcomes guests through private gates into a world of classical architecture and refined finishes. “This home blends classical elegance with modern comfort,” said Bill Earls to Luxury Houses Magazine. “Its location within Port Royal makes it truly one-of-a-kind.”

The main residence showcases four gracious bedroom suites, a whimsical bunkroom with an adjacent bath perfect for children or guests, a richly appointed wood-clad study, and two elegantly designed half bathrooms. Adjacent to the main living quarters, a separate guest house with its own private entrance provides an ideal haven for visitors seeking privacy. The home also features a three-bay garage that ensures ample parking, and a secondary catering kitchen that adds convenience for hosting gatherings.

SEE MORE: Modern $7.5 Million Waterfront Retreat in Tampa Boasts Luxury Wine Lounge

The Master Retreat: A Private Haven

Situated in the most tranquil part of the estate, the master suite offers a retreat-like experience with panoramic views of the water from both the bedroom and its adjoining sunlit reading lounge. The space is complete with a morning bar, opulent bathroom adorned with intricate marble inlays, and finely crafted millwork throughout. “The master wing was designed as a sanctuary,” noted Larry Lappin, Jr., co-listing agent at John R Wood Properties. “Every finish was carefully chosen to evoke comfort, luxury, and privacy.”

SEE MORE: Rooftop Luxury and Waterfront Living Meet at $15.2 Million Smart Home in Surfside

Outdoor Living Reimagined

Stepping outside, one finds lush tropical landscaping that wraps around expansive outdoor spaces, including multiple covered terraces ideal for al fresco dining and relaxation. A built-in outdoor kitchen, a heated swimming pool with a spa and sun shelf, and sweeping views of Smuggler’s Bay combine to create a peaceful oasis for both intimate and grand-scale entertaining. With deeded dock access, boating enthusiasts will find immediate access to the open water, making this home an exceptional waterfront property in the Naples Real Estate market.

As Luxury Houses Magazine discovered, residents of this estate also gain exclusive eligibility for a Primary Port Royal Club Membership. This coveted benefit includes access to one of Naples’ most elite social clubs, featuring a private beach, tennis facilities, fine dining, and a state-of-the-art fitness center. It’s the ultimate extension of a lifestyle already rich in privilege and privacy.

SEE MORE: Live the Royal Palm Yacht Club Dream in Boca Raton, Luxury Estate Listed at $7.9 Million

Location, Community & Lifestyle

For anyone searching for a home in Naples for sale, 3565 Fort Charles Dr is not just a luxurious residence – it embodies a lifestyle. Located in one of the most sought-after neighborhoods in all of Florida, Port Royal is renowned for its security, exclusivity, and sense of community. Residents are within minutes of upscale shopping districts, gourmet restaurants, art galleries, golf courses, and Naples’ famed white-sand beaches. Cultural attractions and high-end conveniences make the area not just livable, but desirable to those seeking elevated coastal living.

“Living here means being part of an unmatched waterfront community,” shared Bill Earls. “Whether it’s morning walks along the shore or sunset cruises from your private dock, life at this property is nothing short of spectacular.”

A Rich Transaction History

Since its initial sale in 2004 for $3,100,000, this property has seen a remarkable evolution. It was listed again in March 2012 for $12,450,000, reflecting significant improvements and market growth. In 2015, the home sold for $9,300,000, and was most recently listed on March 24, 2025, for $29,500,000. A sale record from January 2017 indicating a price of $375,000 is widely believed to be a recording error. These transactions underscore the property’s strong appreciation over time, aligning with broader trends in the Naples home for sale market.

A Distinctive Naples Estate

The estate at 3565 Fort Charles Dr is more than a home; it is a curated lifestyle experience. With six bedrooms and eight bathrooms across nearly 9,000 square feet of interior space, it seamlessly blends indoor luxury with outdoor splendor. The presence of an outdoor kitchen, guest house, catering kitchen, morning bar, tropical gardens, and heated pool and spa underscore the property’s capacity for both relaxation and grand entertaining.

Whether you are an investor, a family seeking a primary residence, or simply someone in search of the finest home in Naples for sale, this estate checks every box. As one of the crown jewels of Naples Real Estate, it continues to attract attention for its prime location, exquisite detailing, and unmatched lifestyle benefits.

For more details, view on Zillow.

For inquiries or to schedule a private showing, please contact:

Bill Earls, PA
239-777-6622
John R Wood Properties

Larry Lappin, Jr.
239-571-8247
John R Wood Properties

* This property might not for sale at the moment you read this post; please check property status at the above Zillow or Agent website links*