Port Royal isn’t a community — it’s America’s highest-end waterfront address. Developer John Glen Sample, a retired Chicago advertising executive, began acquiring mangrove marshland at Naples’ southern tip in 1938, eventually assembling roughly 2 square miles for approximately $50,000. Through the late 1940s and 1950s he funded $3.5M in dredging and canal excavation, shaping the finger-like peninsulas and deep-water waterways that now define the neighborhood. His ambition, in his own words: “to make Port Royal the finest place in the world to live.”

Today approximately 500 estate-sized residences fill those lots, bounded by the Gulf of Mexico to the west and Naples Bay to the east with no bridges to the open Gulf — making Port Royal one of the few true deep-water yachting communities on the Florida coast. The original architectural language, set by Palm Beach architects Howard Major and Henry Harding under Sample’s direction, was Bermuda and British Colonial — “small jewels” about 3,000 sqft in size. Sample feared someone might build too small. He could not have anticipated 2025’s $133M and $225M sales.

The Port Royal Club — Sample’s 1959 beachfront centerpiece — remains the social anchor. Initiation $250K, annual dues $13K. Members get beach, tennis, dining, and a calendar that starts mid-August and runs through mid-July. The Club’s reopening in 2025 after renovation is expected to add 5–10% appreciation to Port Royal values between late 2025 and mid-2026. For kitchen remodels, Port Royal homes fall into three clear vintages: 1950s–1970s Bermuda originals (restoration candidates with original Howard Major / Henry Harding details), 1980s–2000s rebuilds (full teardown-and-rebuild decade where most current inventory was created), and 2010s–2025 new construction (contemporary Stofft Cooney, Kukk Architecture, London Bay, Waterside Builders with near-perfect kitchens that still benefit from stone and appliance refreshes at 5–7 years).