PORT ROYAL: NAPLES EXCLUSIVE WATERFRONT COMMUNITY ALONG GORDON DRIVE

Unveiling Port Royal Real Estate: Luxury, Prestige, and Waterfront Living

Whether it’s the oceanfront mansions with direct Gulf of America beach access or the homes that line the many wide canals providing easy, bridge-free access to the ocean in minutes, Port Royal is all about life on the water.  Most Port Royal homes provide boat docking accommodations right in your backyard, while marinas such as the Hamilton Harbor Yacht Club cater to those looking for full service. This is a community designed from the ground up to be the ultimate haven for boating, named after the famous Jamaican Port that was home to pirates and lavish wealth in the 17th Century.

One of the most famous neighborhoods in Naples, Port Royal has grown to be a fabulous place to live among the elite. Many famous celebrities, including Tom Golisano, John Legere, Scott Kapnick, Richard Schulze, and Peter Gilgan, are owners of beautiful Port Royal homes. To learn more, check out our blog post on ‘Celebrities & Entrepreneurs Who Call Naples/Southwest Florida Home.’ If you are looking for the most luxurious real estate and oceanfront homes for sale in Southwest Florida or want to be a member of the famous Port Royal Club, Port Royal is your Naples Luxury Neighborhood.

We invite you to explore Port Royal to its fullest, search and preview properties below as well as read the additional content after the properties/map.

Experience Port Royal Luxury with Matt Brown

Discover the elegance and exclusivity of Port Royal with Matt Brown. With over two decades of experience, more than $600 million in sales, and recognition among the top 0.5% of real estate professionals nationwide by volume, Matt provides unparalleled expertise in Naples’ most prestigious waterfront community. Whether you’re searching for a grand Gulf-front estate or a canal-front home with deep-water access, Matt’s deep market knowledge and commitment to excellence ensure a seamless buying experience.

Start your journey to Port Royal luxury today. Connect with Matt Brown and find your dream home in Naples’ premier waterfront community.

We invite you to explore Port Royal, Naples, FL, to its fullest, search and preview properties below as well as read the additional content after the properties/map.

Port Royal Homes For Sale

Why is Port Royal so Famous?

  • An exclusive neighborhood built for privacy. With unique neighborhood branding and its unique location, Port Royal deserves the most expensive neighborhood in the United States accolade by Robb Report in 2018.

  • Easy ocean access via Gordon Pass or Keewaydin Island, provides boaters their paradise… an unparalleled beachfront retreat where miles of area estuaries and mangroves become easily navigable which feeds the beautiful calm waters of the Gulf of America.

  • Property Owners Association. Port Royal has a voluntary Property Owners Association dedicated to preserving the community’s first-class ambiance. It enforces deed restrictions and serves as a unified voice for residents, communicating concerns and priorities to the City Council and other government agencies.

  • The Port Royal Club and facilities. Certain Port Royal homes provide eligibility for membership of the ultra-exclusive Port Royal Club. This elegant coastal retreat offers beachside dining, a vibrant tennis scene, state of the art fitness center, and a thriving calendar of year-round events, ensuring that you will love the activities as much as the company.
  • Historical significance and old banyan trees frame picturesque exclusive homes along the famous Galleon Drive and Gordon Drive.  These trees have lived through the entirety of Port Royal’s life, and are a reminder of the history of this unmatched neighborhood.  In the 1950’s John Glen Sample wanted to create a hideaway for the wealthy, he promised to build the “finest place in the world to live,” adding “it can never be duplicated” which has proved true in many ways.
  • Security While Port Royal is not a gated community, security cameras and guards monitor the neighborhood 24/7, ensuring safety and peace of mind for residents.

History of Port Royal

Port Royal, one of Naples’ most prestigious neighborhoods, was once little more than swampland. Inspired by the 17th-century Jamaican port city known for its wealth, Chicago advertising executive John Sample saw the potential to turn this undeveloped land into a world-class waterfront community.

In the early 1950s, large-scale dredging and filling efforts shaped the area into the distinctive canals and peninsulas that now define Port Royal. This massive engineering project transformed wetlands into prime waterfront lots, ideal for the luxury homes Sample envisioned. The first residents moved in by 1952, marking the beginning of the prestigious Port Royal neighborhood.

Sample’s fascination with pirate history influenced not just the community’s name but also its street names, including Rum Row, Spyglass Lane, Galleon Drive, and Buccaneers Roost. His goal was “to make Port Royal the finest place in the world to live,” and today, his vision has been realized. Decades later, Port Royal remains one of the most sought-after luxury communities in the world, known for its deep-water access with serene waterfront views, grand estates, and unmatched exclusivity.

Port Royal Club

Established in 1959, the Port Royal Club is one of the most prestigious private beach clubs in the United States. Reserved exclusively for a highly distinguished group of Port Royal property owners—many of whom rank among the nation’s wealthiest—the club provides a refined beachfront experience tailored to some of the nation’s most discerning homeowners.

Amenities include a pristine stretch of private beach, an Olympic-sized beachfront pool, a state-of-the-art fitness center with personal training, luxurious spa services, and 9 Har-Tru tennis courts with available instruction and tournaments. The club’s calendar features signature social events, including themed dinners, elegant galas, and holiday celebrations.

A new 62,000 square-foot, two-story Clubhouse is currently under construction, elevating its already world-class facilities to new heights. The transformation will enhance member experiences while honoring the club’s longstanding legacy of excellence. Only select Port Royal property owners can apply for membership, with most homes being eligible. Members must apply within 90 days of purchase or maintain eligibility by paying reduced fees.

The new Clubhouse, expected to be complete Q4 of 2026, will provide expansive waterfront vistas and several dining venues to meet the desired experience and expectations of the Members.

  • Dining at the pool/beach level
  • Gulf view dining from main level family casual restaurant and upper floor a la carte restaurant
  • Several bar areas providing indoor/outdoor open seating options
  • Indoor and covered outdoor dining areas sufficiently sized for anticipated demand
  • New beachfront pool area with upgraded lounge chairs, pool furniture and cabanas

Download the Port Royal Club brochure for detailed insights.

With its world-class facilities and exceptional services, the Port Royal Club embodies the luxury and exclusivity that define the Port Royal lifestyle.

Port Royal Club Membership

Membership at the Port Royal Club is exclusive to select residents of the community. Only homeowners south of Palmer Estates and 21st Avenue South are eligible, excluding Aqualane Shores properties on 21st Avenue. To secure membership, residents must opt in within 90 days of purchasing a home with deeded Club eligibility or reserve eligibility by paying 25% of the initiation fee within that timeframe, along with 25% of annual dues each year. If the owner fails to do either within 90 days the property loses it’s Port Royal Club Membership eligibility and as a result the owner or subsequent owner of the property must pay 175% of the then applicable initiation fee in order to join.

  • Initiation Fee: $315,000
  • Annual Dues: $13,500

As one of the most prestigious memberships in Naples, the Port Royal Club offers private access to a beachside pool, fine dining, and premier wellness and social amenities.

Port Royal Neighborhood Real Estate Highlights

The exclusive Port Royal neighborhood is an area of approximately 1.5 square miles, roughly 30% of that being waterways that are navigable to the Gulf of America. Port Royal consists of 640 single-family homes and no condominiums. The Port Royal area is about 2 miles North to South along the Gulf of America and 1 mile from East to West at the widest from Naples Bay to the Gulf.

Port Royal is primarily comprised of luxurious canal-front homes situated on lots of approximately 1/2 acre. Additionally, there are beachfront estates located directly on the Gulf of America, with lot sizes ranging from 1/2 acre to over 5 acres, offering some of the most exclusive real estate in Naples.

Contact Matt Brown to find waterfront homes, luxury condos & homes for sale in Port Royal.

  • 17 single-family homes sold in Port Royal in 2024 at an average price of $17,997,647 ($2,470 per square foot), an average size of 7,329 square feet. The highest home sale price of 2024 in Port Royal was $36,490,000 ($3,469 per square foot) for a 2020 home designed by Kukk Architecture and built by A. Vernon Allen at 3675 Fort Charles Drive on a 0.95 acre lot with 10,520 square feet of living space and 5 bedrooms, a den, 6 full bathrooms, 3 half bathrooms and 4 garage spaces.

Aerial map of Port Royal, Fl real estate luxury homes for sale

Dining, Shopping and Entertainment

For a resort style living with truly exclusive entertainment, dining, socializing and more, The Port Royal Club is restricted to homeowners in the community.  Old Naples offers Fifth Avenue South and Third Street South which are two iconic venues with impressive lists.  There are so many places to recommend and it’s hard to pick favorites but Ocean Prime and Sails Restaurant won’t disappoint.  And if venturing to 3rd Street South, try The Continental or Campiello, their outdoor setting and atmosphere give you the Southwest Florida lifestyle we all desire. For more dining information, visit our restaurant page.

Similar to downtown Naples dining, shopping at both Third Street South and Fifth Avenue South are equally impressive.  Walking along both downtown streets, you will be drawn to unique boutiques, cute gift shops, and more.  And while you venture, there are plenty of pick-me-up local options we recommend trying; 5th Avenue Coffee Company, Bad Ass Coffee of Hawaii, Divine Naples Coffee and Wine, and The Brick Coffee Bar all get my business frequently.

Sitting on the water, Port Royal is the doorway to an entire ocean of entertainment for boat lovers, but there’s more than just life on the water to be found here.  Away from the water, you can bask in the 170 acres of plants and parkland in the Naples Botanical Gardens, enjoy performances at The Gulfshore Playhouse or The Naples Players, or enjoy the plethora of artistic events by Naples Art District. Visit Naples Art Scene for more information.

Things To Do In Port Royal

GOLF

As one of the premier golf communities in the world with 80+ championship courses, Naples is home to golfing for all levels and competitiveness.  If you are looking for private memberships, Royal Poinciana and Grey Oaks Country Club are good places to start. Check out our blog post for more information on the Top 15 Naples Private Golf Courses.

Away from the links, you can indulge your love of boating at a number of yacht clubs.  Naples Yacht Club and Naples Sailing and Yacht Club providing fantastic amenities and wonderful communities of like-minded individuals. Get more information about popular yacht clubs and marinas – visit Boating+.

If you’re thinking about building your own dock, our blog post offers detailed insights into The Real Costs of Building and Maintaining a Backyard Boat Dock.

Naples has a vibrant calendar of events covering everything from exhibitions to festivals.  With something for everyone, Naples Events alongside a number of location-specific options at 5th Avenue South Events and 3rd Street South Events, there is always something to see or do in Naples.

Visitors can enjoy a broad choice of hotels covering every taste and need in Naples.  Highlights include The Inn on Fifth, Bellasara Resort, Naples Bay Resort, and The Ritz Carlton. If looking for dining recommendations, visit our Restaurants+ page.

Schooling

Naples has an excellent reputation for its education department, with the Collier County Public Schools District winning an “A” rating from the Florida Department of Education three years running. As of 2020, there are 54,000+ students and 90+ public and private schools throughout Naples with a wide choice of both public and private schools around the Port Royal neighborhood, including:

Public:

  • Lake Park Elementary
  • Gulfview Middle School
  • Naples High School
  • Mason Classical Academy (Charter)

Private:

  • Saint Ann School
  • Community School of Naples
  • Seacrest Country Day School
  • The Village School

For more information, check out GreatSchools to explore the local schools.

Prime Location

This private oasis located at the southern end of Naples, west of U.S. 41, is bordered by Aqualane Shores to the north, the Gulf of America to the west, Naples Bay to the east, and Gordon Pass to the south. In addition to luxurious waterfront living, the coveted Port Royal neighborhood offers residents a short drive or bike ride to Old Naples, where they can enjoy upscale dining, shopping, and cultural attractions along 5th Avenue South.

Nearby Places to Visit near Port Royal (drive time)

  • Naples Pier – 5 minutes
  • Naples Beach – 6 minutes
  • Cambier Park – 7 minutes
  • Naples Train Museum – 9 minutes
  • Downtown Naples – 9 minutes
  • Lowdermilk Park – 11 minutes
  • Baker Park – 11 minutes
  • The Naples Preserve – 12 minutes
  • Conservancy of Southwest Florida – 13 minutes
  • Fleischmann Park – 13 minutes
  • Naples Zoo at Caribbean Gardens – 15 minutes
  • Collier Museum at Government Center – 15 minutes
  • Gordon River Greenway Park – 15 minutes
  • Freedom Park – 16 minutes
  • Naples Botanical Garden – 17 minutes
  • Sugden Regional Park – 17 minutes
  • Naples Pickleball Center – 17 minutes
  • Bayview Park – 18 minutes
  • The Village Shops on Venetian Bay – 18 minutes
  • Clam Pass Park – 21 minutes
  • Waterside Shops – 21 minutes
  • Artis-Naples – 22 minutes
  • Mercato – 25 minutes
  • Delnor-Wiggins Pass State Park – 30 minutes
  • Golisano Childrens Museum of Naples – 31 minutes
  • Wonder Gardens – 38 minutes
  • Marco Island – 39 minutes
  • Sanibel Island – 1 hour 33 minutes

Port Royal: Proximity to Airports (drive time)

  • Southwest Florida International Airport (RSW) – 48 minutes drive
  • Naples Airport (APF)- 17 minutes drive
  • Punta Gorda Airport (PGD) – 1 hour 15 minutes
  • Sarasota Bradenton International Airport (SRQ)- 2 hours 14 minutes
  • Fort Lauderdale–Hollywood International Airport (FLL)- 1 hour 48 minutes
  • Miami International Airport (MIA) – 2 hours 15 minutes
  • Tampa International Airport (TPA) – 2 hours 51 minutes

Find Your Port Royal Dream Home with Matt Brown

Ready to experience the unparalleled luxury of Port Royal? Let Matt Brown, recognized among the top 0.5% of real estate professionals nationwide by volume and one of the top 50 in Naples, guide you to the finest waterfront estates in this prestigious community. With Matt’s expertise and dedication, securing your ideal home in Port Royal is effortless.

Contact Matt Brown at (239) 580-8864 or fill out the Let’s Connect form today. Read what Matt’s clients have to say and discover why buyers and sellers trust him for exceptional results. Begin your journey to exclusive waterfront living with Matt Brown Real Estate.

Port Royal FAQs

  1. What types of homes for sale are available in Port Royal?
    Port Royal consists exclusively of single-family estate homes. Most properties are waterfront, with canal-front homes on approximately 1/2-acre lots and Gulf-front homes on larger lots ranging from 1/2 acre to over 5 acres.
  2. Does Port Royal have condos?
    No, Port Royal is strictly a single-family home community. There are no condominiums within the neighborhood.
  3. Does Port Royal have a homeowners association (HOA)?
    Port Royal does not have a formal HOA, but the Port Royal Property Owners Association (PRPOA) exists to preserve the community’s integrity and advocate for residents. Membership is voluntary.
  4. Who can join the Port Royal Club?
    Only Port Royal homeowners living south of Palmer Estates and 21st Avenue South are eligible for membership. New homeowners must opt in within 90 days of purchase or reserve eligibility by paying 25% of the initiation fee and 25% of annual dues each year.
  5. Is Port Royal a golf community?
    No, Port Royal does not have a golf course. However, the Port Royal Club offers extensive amenities, including tennis courts, a fitness center, spa services, and private beach access.
  6. Why is Port Royal so expensive?
    Port Royal’s deep and wide canals allow large yachts to navigate and turn easily, a rare feature in Naples. The custom-built luxury Port Royal homes sit on large lots and offer prime waterfront access. This combination makes Port Royal one of the most desirable and valuable real estate markets in Florida.
  7. How close is Port Royal to Downtown Naples?
    Port Royal is located just minutes south of Downtown Naples, making it convenient for residents to access 5th Avenue South, 3rd Street South, and other shopping, dining, and entertainment options.
  8. Can you dock a boat at a Port Royal home?
    Yes, many Port Royal homes feature private deep-water docks with direct access to Naples Bay and the Gulf of America, making it one of the most desirable boating communities in Southwest Florida.
  9. What makes Port Royal one of the most exclusive communities in Naples?
    Port Royal is known for its sprawling waterfront estates, private beach club, and direct Gulf access. It is home to some of the most expensive real estate in Florida, attracting high-net-worth individuals who value privacy, luxury, and world-class amenities.