As the historic and architectural heart of Naples, Old Naples is a favorite spot for design aficionados. Extending north from the Aqualane Shores neighborhood between 14th and 15th Avenues South to 7th Avenue North and stretching west from the Tamiami Trail and Naples Bay to the Gulf of Mexico, this 1.5-square-mile enclave blends vintage charm with modern coastal grandeur. Lush avenues vanishing into pearl white beaches, historic homes mingling with luxury estates, and an exclusive high-end lifestyle define its appeal.
Architectural Evolution: From Cottages to Contemporary Estates
The neighborhood began in the late 1880s, when the original town site was first laid out along the beach. It earned its name in honor of Italy's Bay of Naples—its promise of beauty and sophistication realized in early investments and the construction of the Naples Pier.
Today, you'll find early frame cottages with subtle period details alongside Mediterranean Revival villas and grand Coastal Contemporary estates. Townhomes and low-rise condos offer an upscale alternative to single-family residences. Construction standards are high—custom builders create residences designed to withstand coastal weather, while providing refined finishes and sustainable performance.
Though much of Old Naples has been redeveloped, many vintage homes—especially near 5th Avenue and the Pier—have been carefully restored. Conversely, what began as Millionaire's Row—a stretch of early 20th-century beachfront estates—has evolved into some of the country's most expensive real estate. With recent oceanfront sales in the $25 million to $35 million range and off-market transactions commonplace, including purchases of $85 million and $225 million, the activity underscores Naples's global luxury standing.
Today, you'll find early frame cottages with subtle period details alongside Mediterranean Revival villas and grand Coastal Contemporary estates. Townhomes and low-rise condos offer an upscale alternative to single-family residences. Construction standards are high—custom builders create residences designed to withstand coastal weather, while providing refined finishes and sustainable performance.
Though much of Old Naples has been redeveloped, many vintage homes—especially near 5th Avenue and the Pier—have been carefully restored. Conversely, what began as Millionaire's Row—a stretch of early 20th-century beachfront estates—has evolved into some of the country's most expensive real estate. With recent oceanfront sales in the $25 million to $35 million range and off-market transactions commonplace, including purchases of $85 million and $225 million, the activity underscores Naples's global luxury standing.
An Opulent Design Acumen
That said, the mansions of Old Naples represent more than luxury—they embody coastal history, architectural storytelling, and an enduring lifestyle of refinement. And as you might expect, the interiors of properties in Old Naples are often just as stunning as the exteriors, if not more so.
It starts with the Naples Historic District, spanning roughly 500 acres between Ninth Avenue South and Gulf Shore Boulevard, preserving 65 historic houses and highlighting the city's heritage between 1887 and 1937. Contributing properties are found on Broad Avenue, Second Street, Third Street, and Twelfth through Thirteenth Avenues. Historic Palm Cottage (137 12th Avenue South), built in 1895, remains Naples' oldest surviving structure. As a rare example of tabby-mortar vernacular architecture, the home was a precursor to the neighborhood's eclectic and constantly evolving design aesthetic.
Additionally, the glamorous, artistic vibes that emanate from the galleries on Fifth Avenue South and Third Street South often find their way into many of these homes. Whether it's a restored 1920s cottage nestled in tropical foliage or a sweeping modern villa overlooking the Gulf, each property echoes centuries of curated taste and enduring elegance.
It starts with the Naples Historic District, spanning roughly 500 acres between Ninth Avenue South and Gulf Shore Boulevard, preserving 65 historic houses and highlighting the city's heritage between 1887 and 1937. Contributing properties are found on Broad Avenue, Second Street, Third Street, and Twelfth through Thirteenth Avenues. Historic Palm Cottage (137 12th Avenue South), built in 1895, remains Naples' oldest surviving structure. As a rare example of tabby-mortar vernacular architecture, the home was a precursor to the neighborhood's eclectic and constantly evolving design aesthetic.
Additionally, the glamorous, artistic vibes that emanate from the galleries on Fifth Avenue South and Third Street South often find their way into many of these homes. Whether it's a restored 1920s cottage nestled in tropical foliage or a sweeping modern villa overlooking the Gulf, each property echoes centuries of curated taste and enduring elegance.
Notable Mansions and Residences of Old Naples
Old Naples combines rich history with bespoke coastal architecture. At the same time, many estates are newly constructed, boasting classic lines and stunning interiors and designs that honor the area's pleasing coastal aesthetics and luxury lifestyle.
680 8th Avenue North (1929 Captain Parker House)
Just steps from 5th Avenue South and the Gulf, one of Old Naples' earliest landmark residences was built as a statement of coastal permanence—the 1929 Captain Parker House. Beautifully restored, this gem, spanning just over 3,000 square feet, blends timeless charm with modern luxury. Historic features like heart pine flooring, shiplap walls, and a fireplace framed in oyster shells pair seamlessly with contemporary, but period-respectful touches such as a Lacanche range and a designer soaking tub. Outdoors, a grotto-style pool and lush tropical landscaping—including a 50-foot Royal Poinciana—create a private oasis. With impact glass, a metal roof, and a whole-house generator, this romantic cottage offers refined coastal living in one of Naples' most cherished and walkable neighborhoods.
616 Bougainvillea Road
A premier example of Old Naples' new construction idiom, 616 Bougainvillea Road sits on a half-acre lot backing to a small lake with western views. A striking example of scale, symmetry, and sophistication, the home boasts nearly 9,500 square feet of living space—an impressive architectural footprint that blends seamlessly with the understated elegance of the surrounding village. Inside, the ambiance is defined by meticulous architectural clarity—grand formal living and dining rooms, bespoke millwork, expansive gallery-style corridors, and multiple wings thoughtfully designed for entertaining. Every space flows with purposeful grace, uniting modern luxury with the timeless charm of Old Naples.
111 5th Avenue South
Among the most eye-catching of Old Naples' 21st-century builds, the French Colonial-inspired residence at the prestigious corner of Fifth Avenue South and Gulf Shore Boulevard is clad in over $1 million of imported Italian marble and spans 7,300 square feet. Designed for refined living and entertaining, it features five en-suite bedrooms, a study, a chef's kitchen with three islands, a rooftop sunset deck, and a seven-car garage. Indoor-outdoor flow is effortless, with a covered outdoor kitchen, expansive living areas, and a 70-foot pool set amid manicured grounds. Just steps from the Gulf and downtown, this custom-built residence is a showpiece of timeless elegance and exceptional craftsmanship.
Explore More of the Naples Luxury Lifestyle with a Trusted Local Expert
Although Naples Beach and the modern waterfront estates that sit just west of Gulf Shores Boulevard are a primary draw, the Old Naples neighborhood is a revelation of the area's deep heritage and artful soul. It's a place where history lives on in clapboard cottages, and the artistry of locals, transplants, and visitors alike fills the streets with a cultural vitality that continues to paint this stretch of Southwest Florida in rich, joyous hues.
Whether you're catching a live performance at Sugden Theatre, strolling through a Fifth Avenue South gallery, or admiring the preserved architectural beauty of the Naples Historic District, Old Naples invites you to be more than a spectator but a participant in a neighborhood where creativity and sophistication are always in season.
If you're interested in a home or investment property in Old Naples—or considering listing one of the area's grand residences for sale—contact Andrew Christopher today to start your Naples real estate journey. From waterfront estates to historic properties, let Andrew's experience and decades of firsthand knowledge of Old Naples guide you through this extraordinary and highly sought-after luxury real estate market.
Whether you're catching a live performance at Sugden Theatre, strolling through a Fifth Avenue South gallery, or admiring the preserved architectural beauty of the Naples Historic District, Old Naples invites you to be more than a spectator but a participant in a neighborhood where creativity and sophistication are always in season.
If you're interested in a home or investment property in Old Naples—or considering listing one of the area's grand residences for sale—contact Andrew Christopher today to start your Naples real estate journey. From waterfront estates to historic properties, let Andrew's experience and decades of firsthand knowledge of Old Naples guide you through this extraordinary and highly sought-after luxury real estate market.