Port Royal: The Pinnacle of Luxury Waterfront Living in Naples, Florida

At Naples Florida Real Estate by Chris Nightingale, we are thrilled to introduce Port Royal, the epitome of luxury and exclusivity in Naples, Florida. Renowned as one of the most prestigious waterfront communities in the United States, Port Royal offers an unparalleled lifestyle defined by opulent estates, deep-water canals, and direct Gulf of Mexico access. Spanning approximately 500 acres along Naples Bay and the Gulf, this non-gated community is a haven for affluent buyers seeking sophistication, privacy, and a vibrant coastal lifestyle. Developed by visionary John Glen Sample, Port Royal has set the standard for luxury living since its inception in 1959. Below, we explore the key features, home types, amenities, and essential details that make Port Royal a coveted destination for discerning homebuyers.

Key Features of Port Royal

World-Class Waterfront Access

Port Royal is celebrated for its deep, wide canals and direct, no-bridge access to the Gulf of Mexico via Gordon Pass, making it a premier destination for boating enthusiasts. Many homes feature private docks capable of accommodating yachts up to 70 feet or larger, depending on the property’s waterfront frontage (typically 100–250 feet). This unique infrastructure, designed for large motor and sailing yachts, ensures seamless navigation to Naples Bay and beyond, offering residents a true nautical lifestyle.

Prime Location Near Olde Naples

Located just south of Olde Naples and Aqualane Shores, Port Royal is minutes from the upscale shopping, fine dining, and cultural attractions of 5th Avenue South and 3rd Street South. Residents enjoy proximity to iconic landmarks like the Naples Pier, Naples Botanical Gardens, and Artis-Naples, with Southwest Florida International Airport (RSW) just a 35-minute drive away via I-75. This prime location blends serene waterfront living with easy access to Naples’ vibrant urban amenities.

Exclusive Port Royal Club Membership

The Port Royal Club, established in 1959, is a private, residents-only club that serves as the community’s social and recreational hub. Membership is exclusive to homeowners south of 21st Avenue South (excluding Aqualane Shores properties on 21st Avenue), offering access to a beachside Olympic-sized pool, nine Har-Tru tennis courts, a state-of-the-art fitness center, spa services, and formal and informal dining. The club hosts a robust calendar of social events, including seafood buffets, holiday parties, and New Year’s Eve fireworks, fostering a strong sense of community. Membership requires opting in within 90 days of purchase or paying 25% of the initiation fee (currently $100,000) and 25% of annual dues ($8,900), with non-compliance resulting in a 175% initiation fee for future owners.

Historic and Prestigious Legacy

Conceived by John Glen Sample in 1938, Port Royal transformed a mangrove swamp into a world-class community starting in 1959. Inspired by the opulent 17th-century Jamaican pirate port, the neighborhood features street names like Galleon Drive, Rum Row, and Spyglass Lane, evoking its nautical heritage. The Port Royal Property Owners Association ensures that new construction and renovations maintain the community’s high standards of quality and aesthetic, preserving its reputation as Naples’ most elite neighborhood.

Types of Homes for Sale in Port Royal

Port Royal exclusively features custom-built single-family homes and estates, with no condominiums or attached residences. These luxurious properties, often designed by renowned architects like Stofft Cooney, Kukk Architecture, and MHK Architecture, range from 3,000 to over 10,000 square feet, with prices typically between $6.95 million and $210 million. Homes are situated on large lots (0.5 to 5+ acres) along deep-water canals, Naples Bay, or the Gulf of Mexico, offering breathtaking views and premium finishes like limestone floors, pewter white oak, and smart home technology. Below are the primary home types available.

Canal-Front Estates

• Canal-Front Estates: These homes, located along Port Royal’s deep-water canals (e.g., Man of War Cove, Smugglers Bay), range from 3,000 to 8,943 square feet, typically offering 4–7 bedrooms, 4–9 bathrooms, and 3–5 car garages. Features include private docks, open floor plans, gourmet kitchens with Wolf/Subzero appliances, and outdoor living areas with infinity-edge pools and automated screens. Prices range from $6.95 million to $30 million. For example, a 5-bedroom, 7-bath estate at 575 Admiralty Parade West, sold for $85 million in April 2025, features 107 feet of Hidden Bay shoreline and direct Gulf access.

Beachfront Estates

• Beachfront Estates: Positioned along Gordon Drive, these Gulf-front homes range from 5,000 to 10,000 square feet, offering 5–8 bedrooms, 6–10 bathrooms, and 3–8 car garages. These properties, often on lots up to 5 acres, feature wraparound porches, resort-style pools, and panoramic Gulf views. Prices range from $20 million to $210 million, with a notable example being the Gordon Pointe compound (9+ acres, 800 feet of beach frontage) listed for $295 million in 2024. These homes are eligible for immediate Port Royal Club membership and are built to stringent FEMA codes.

Custom-Built Residences

• Custom-Built Residences: Many homes in Port Royal are newly constructed or renovated, featuring modern coastal or West Indies-style designs. These residences, ranging from 4,000 to 8,200 square feet, include 4–6 bedrooms, 5–9 bathrooms, and 3–5 car garages. Highlights include smart home systems (e.g., Lutron, Savant), exotic stone finishes, and expansive outdoor areas with pools, spas, and outdoor kitchens. Prices range from $10 million to $50 million. A 6-bedroom, 10-bath home at 1672 Galleon Drive, sold for $46.8 million in 2023, exemplifies this category with its modern elegance and Hidden Bay views.

Amenities Within Port Royal

Port Royal’s amenities, centered around the exclusive Port Royal Club, cater to residents seeking a luxurious, active, and social lifestyle. The community’s waterfront setting and proximity to Naples’ attractions further enhance its appeal.

Port Royal Club

The Port Royal Club, located at 2900 Gordon Drive, is a private, residents-only facility offering a beachside Olympic-sized pool, nine Har-Tru tennis courts, a fitness center with modern equipment, spa services, and formal and informal dining. The club, designed as a “gracious extension of your Port Royal home,” hosts events like Friday night seafood buffets, bridge tournaments, and New Year’s Eve fireworks. A planned two-story rebuild by Champalimaud Design, following Hurricane Ian’s impact in 2022, promises enhanced facilities. Membership is a key draw, with initiation fees of $100,000 and annual dues of $8,900.

Boating and Waterfront Activities

Port Royal’s deep-water canals and direct Gulf access make it a boater’s paradise. Most canal-front homes feature private docks, accommodating yachts up to 70 feet or larger, with no bridges to navigate to Gordon Pass. Residents can access nearby marinas like Naples Yacht Club, Hamilton Harbor, or Naples Sailing and Yacht Club for additional boating services. Kayaking, paddleboarding, and fishing are also popular along Naples Bay and the surrounding waterways.

Proximity to Naples’ Attractions

While Port Royal itself is a serene enclave, residents are just 2–4 miles from downtown Naples’ 5th Avenue South and 3rd Street South, offering upscale dining, boutique shopping, and cultural venues like Artis-Naples. Nearby recreational options include the Naples Pier, Lowdermilk Beach, and over 80 championship golf courses, such as Royal Poinciana and Grey Oaks Country Club, accessible via private memberships. The community’s location also provides easy access to Cambier Park’s athletic facilities and the Naples Botanical Gardens.

Security and Privacy

Although not gated, Port Royal ensures resident safety with 24-hour security vehicle patrols and surveillance cameras. Many homes are individually gated, offering additional privacy. The community’s low-density design and strict building regulations, enforced by the Port Royal Property Owners Association, maintain its exclusive and refined aesthetic.

Community Details

Community Size

Port Royal spans approximately 500 acres, encompassing a network of deep-water canals, Naples Bay frontage, and Gulf of Mexico beachfront. The community’s low-density layout, with large lots ranging from 0.5 to 5+ acres, ensures privacy and expansive waterfront views.

Number of Homes

Port Royal is home to approximately 560–640 single-family homes, creating an intimate and exclusive community. The variation in estimates reflects ongoing development and lot subdivisions, such as the Gordon Pointe compound.

Year Built

Development of Port Royal began in 1959, spearheaded by John Glen Sample, with many original homes now renovated or replaced with modern estates. Construction continues, with new homes built to stringent FEMA and City of Naples codes, particularly post-Hurricane Ian in 2022.

Why Choose Port Royal with Naples Florida Real Estate?

At Naples Florida Real Estate by Chris Nightingale, we specialize in navigating the ultra-luxury market of Port Royal. With over 20 years of experience in Southwest Florida, our team offers unparalleled expertise, access to exclusive listings, and personalized guidance to help you secure your dream home. Whether you’re seeking a canal-front estate with a private dock, a Gulf-front mansion, or a custom-built masterpiece, we’ll tailor your search to your unique needs and ensure a seamless buying process. We also provide expert advice on Port Royal Club membership eligibility and local building regulations.

Contact us today to explore Port Royal’s current listings, schedule a private viewing, or learn more about this iconic community’s lifestyle and investment potential. Let Naples Florida Real Estate by Chris Nightingale guide you to your slice of paradise in Naples’ most prestigious neighborhood!

Where Is Port Royal?

Port Royal in Naples, Florida, is renowned as one of the most elite and prestigious waterfront communities in the United States, offering a unique blend of luxury, exclusivity, and coastal living. Here are the defining characteristics of real estate and homes in Port Royal:

• Property Types and Architecture: Port Royal consists exclusively of single-family estate homes—there are no condos. Most properties are custom-built, offering a mix of architectural styles including Mediterranean-inspired villas, contemporary Caribbean, island influences, and sleek modern estates. The homes are designed with meticulous attention to detail and luxury finishes, often set on expansive lots with manicured lawns, towering palms, and privacy walls. Homes typically range from 3,000 to well over 10,000 square feet, with some Gulf-front properties sitting on multiple-acre estates.
• Waterfront Living: About 95% of homes are directly on the water, either facing the Gulf of Mexico or deep, wide canals that offer direct and bridge-free access to the ocean. Most residences feature private boat docks—ideal for yacht owners—and many have swimming pools and extensive outdoor living spaces. The proximity to water and access to boating is a core lifestyle feature, with homeowners able to reach open Gulf waters from their backyards.
• Prices and Market Trends: Real estate in Port Royal is among the most expensive in the country. As of July 2025, the median listing price for homes was $24.4 million, with some homes, like the famed Gordon Pointe estate, listed well above $200 million. The price per square foot averages over $3,000, and prices have risen significantly in recent years. Even vacant lots can command $15 million or more. The average sale price for homes recently was around $16.5 million, marking an increase of 22.9% to 37.3% year-over-year.
• Community and Lifestyle: Port Royal is celebrated for its tight-knit, discreet, and affluent community. Homeowners have the option to join the prestigious Port Royal Club, which offers private beach access, tennis courts, a fitness center, spa services, and a social hub. The community is only minutes from downtown Naples, fine dining, shopping, and cultural attractions. Residents enjoy high security, manicured surroundings, and a peaceful, private environment.
• Homeowner Demographics: The neighborhood attracts high-net-worth individuals, celebrities, and successful entrepreneurs, drawn by its privacy, luxury, and the ability to dock large yachts. Many homes are seasonally occupied, indicating a high proportion of second or vacation homes.
• No Condos or Golf: Port Royal is a single-family home community only and does not have a golf course. However, neighboring areas offer plenty of golfing opportunities, and the amenities within Port Royal focus on waterfront and beach activities.
• Market Dynamics: Port Royal homes tend to stay on the market longer than the average U.S. home, often taking months to sell, and may sell below listing price. However, demand and prestige remain strong, making it a stable investment for luxury buyers.