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OLDE NAPLES, FLORIDA

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Olde Naples – Historic Charm, Coastal Elegance & the Heart of Downtown Naples

Olde Naples is one of the most iconic and beloved neighborhoods in Naples, Florida — a timeless coastal district where historic charm, tropical beauty, and modern luxury blend seamlessly. Known for its signature streets lined with coconut palms, walkable beach access, and a relaxed yet refined atmosphere, Olde Naples captures the essence of classic Florida living.

This historic neighborhood traces its origins back to the late 19th century, with its official founding in 1886. One of its most treasured landmarks, the Palm Cottage, built in 1895, remains the oldest surviving home in Naples and a symbol of the area’s rich heritage.

Today, Olde Naples offers a unique mix of original Florida cottages, elegant single‑family estates, and contemporary luxury residences — all set within a lush, coastal environment that feels both vibrant and serene.

A Walkable Coastal Village

One of the defining features of Olde Naples is its walkability. Nearly every street leads directly to the beach, creating a rare and highly desirable lifestyle where residents can stroll from home to the Gulf of Mexico in minutes.

The neighborhood is also home to Naples’ most celebrated destinations:

  • 5th Avenue South – upscale dining, boutiques, galleries, and cultural events
  • 3rd Street South – charming cafés, historic architecture, and luxury shopping
  • Naples Pier – a beloved landmark for sunsets, fishing, and dolphin watching

This combination of beach access, culture, and walkable luxury makes Olde Naples one of the most sought‑after communities in Southwest Florida.

Architecture & Lifestyle

Walking through Olde Naples reveals a captivating blend of architectural styles:

  • Restored historic cottages
  • Classic Florida ranch homes
  • Mediterranean‑inspired estates
  • Modern coastal new construction
  • Luxury villas and low‑rise condominiums

Each property is surrounded by mature landscaping, tropical gardens, and quiet streets that preserve the neighborhood’s intimate, village‑like feel.

Residents enjoy a lifestyle defined by:

  • Beach walks at sunrise and sunset
  • Outdoor dining and boutique shopping
  • Art festivals, cultural events, and live music
  • A friendly, welcoming community atmosphere

Olde Naples is a place where luxury feels effortless and everyday life feels like a vacation.

History & Timeless Appeal

From its early days as a small coastal settlement to its evolution into one of Naples’ most prestigious neighborhoods, Olde Naples has maintained its charm and authenticity. The preservation of historic sites, combined with thoughtful redevelopment, has created a community that honors its past while embracing modern elegance.

Why Buyers Love Olde Naples

  • Walkable lifestyle with direct beach access
  • Historic charm blended with modern luxury
  • Proximity to 5th Avenue South & 3rd Street South
  • Iconic landmarks like Naples Pier & Palm Cottage
  • Lush, tropical streetscapes and mature landscaping
  • Wide range of architectural styles and property types
  • Vibrant cultural scene, dining, and boutique shopping

Ideal for: Buyers seeking a refined coastal lifestyle, walkability, historic character, and a central location in one of Naples’ most prestigious and picturesque neighborhoods.

Homes for Sale in Olde Naples

From cozy beach cottages to elegant mansions and upscale condominiums, the homes for sale in Olde Naples run the entire architectural spectrum. Thanks to strict building codes, all the beachfront residences in the community are single-family homes; you won’t find high-rise condos on the beach in Olde Naples.

OLDE NAPLES PROPERTIES

A striking custom contemporary residence ideally positioned in one of downtown Naples’ most sought-after neighborhoods, just a short stroll to the beach and the new Four Seasons Naples Beach Resort. Set on an expansive and private 0.30-acre west facing homesite and built 3 feet above FEMA’s current level with no water close to property or a garage level during any hurricane. This exceptional pool home offers the rare combination of architectural presence, refined interiors, fine craftsmanship with extraordinary attention to details, luxury finishes in a premier coastal location in the very heart of Naples. Built in 2013 and designer renovated in 2023, the home offers 3,843 SF under air and 7,576 total, featured in "Florida Design" and “Gulf Shore Life” design magazines, the home welcomes you through an inviting double door entrance and foyer with 22ft soaring ceilings. Thoughtfully designed for both elegant entertaining and everyday living, the main level features a private study with custom built-in cabinetry, a spacious primary suite with a spa-inspired bathroom including a soaking tub, separate shower, a generous walk-in closet, and a conveniently located laundry room. Sliding glass doors lead to an open sitting area overlooking the private garden and 50 foot double infinity edge pool. The light-filled great room is the centerpiece of the home, showcasing dramatic 18ft ceiling height, a linear double-sided fireplace and a stunning a floor to ceiling wall of glass that frames views of the private oversized backyard, pool and decks. Adjacent is the dining area and a chef’s gourmet kitchen, oversized island with quartz countertops, and imported custom cabinetry, all with picturesque pool and garden views. Sliding glass doors open to a covered lanai designed for year-round enjoyment, complete with a linear fireplace, brand new outdoor kitchen and grill, electric screened enclosure with surrounding lounge decks and pool that creates a serene and private outdoor retreat. The second level presents two generously sized en-suite guest bedrooms, a second-floor laundry, and access, via a sculptural feature spiral staircase, to an open rooftop deck—an extraordinary vantage point to entertain and enjoy sweeping city and sneek Gulf views and exceptional sunsets. Additional highlights include a two-car garage, a custom grass paver driveway and beautiful landscaping. Ideally located just minutes from Fifth Avenue South’s renowned fine dining, boutique shopping, galleries, and cultural venues. Never previously offered to the market, this represents an opportunity to own this exceptional designer residence. $7,295,000 Active

652 Bougainvillea RD NAPLES, Florida

3 Beds 4 Baths 3,843 SqFt 0.3 Acres

Welcome to this striking coastal contemporary residence in the heart of Naples, built in 2021 and offered fully furnished. Designed by renowned interior designer Jeffery Fischer, this light-filled two-story home blends refined architecture, elevated design, and seamless indoor-outdoor living. Privately set behind lush tropical landscaping, the property lives like a quiet, serene compound, offering remarkable privacy and tranquility while just blocks from 5th Avenue South dining and shopping, the Gulf's white sand beaches and new Four Seasons Hotel. A dramatic entry opens to soaring ceilings, wide-plank wood flooring and an impressive open staircase with gallery overlook. The thoughtfully designed floor plan offers approximately 3,290 square feet of living area, featuring four bedrooms, three full baths, a powder bath and a dedicated pool bath. The private primary suite overlooks the tranquil pool and spa, creating a peaceful retreat filled with natural light. The chef's kitchen is stunning and functional, featuring Thermador appliances and a Miele built-in coffee system, and highlighted by a large waterfall island, custom cabinetry, statement backsplash and a gas range supplied by propane. The main living area opens effortlessly to the outdoor lounge and covered lanai, creating an indoor-outdoor lifestyle ideal for entertaining. $6,200,000 Active

790 6th AVE N NAPLES, Florida

4 Beds 5 Baths 3,290 SqFt 0.18 Acres

In the private, gated enclave of Gordon Drive Estates a mere three doors from the sugar sand coastline, lies this meticulously maintained, custom home enveloped by lush, tropical foliage. The entire residence is defined by volume ceilings, as well as large sliders and transom windows that allow natural light to pour in and create a warm, comfortable ambiance. The floor plan flows through 3,033 sq. ft. of living space - all culminating in the spacious atrium that is perfect for entertaining. The kitchen is open to the family room and features two center islands, granite countertops, Viking appliances, a pantry, and custom cabinetry. Secluded and offering the utmost in privacy, the master suite is sprawling and is accompanied by a luxurious bath with Carrera marble flooring, a soaking tub that is flanked by a fireplace, and spacious walk-in shower. The home also encompasses a charming second bedroom with private bath, a cabana guest suite with private entrance, and a study. Gordon Drive Estates offers tranquility and luxury with its resident-only gated beach access, as well as enjoys the convenience of being located within seconds to the renowned shopping and dining found on Third Street South. Additionally desirable and worth note is that this home did not receive any interior water intrusion during recent storms, including Ian. $6,900,000 Active

2080 Gordon DR NAPLES, Florida

3 Beds 4 Baths 3,033 SqFt 0.45 Acres

Introducing a truly rare offering in the heart of Olde Naples, this beautiful designer-renovated corner residence epitomizes refined coastal living. Located mere steps from the pristine Gulf beaches and vibrant Fifth Avenue, this exceptional 2-bedroom, 2-bath residence offers a blend of modern design and timeless charm.Upon entering, you'll be greeted by Porcelanosa vinyl flooring throughout, enhancing the light-filled spaces. The spacious bedrooms each feature their own private en-suite baths and custom closets providing an ideal sanctuary. Each bathroom is complete with Porcelanosa fixtures and tile.The gourmet kitchen is a standout, designed for both daily living and entertaining. It features stunning quartz countertops and top-of-the-line Bosch appliances. You’ll also find a discreet in-unit washer/dryer.Additional highlights include an outdoor sitting area, which is perfect for morning coffee or an evening cocktail. The residence also includes a covered private parking space, as well as a private storage shed which is ideal for bikes and beach gear. The Buttonwood is a small boutique building where you’ll find friendly neighbors that respect your privacy.This bright, modern, and chic residence is truly the best in the market. It's ideally located in a quiet, serene setting, offering lovely views from every window, yet within walking distance to beaches, shopping and dining. A true crown jewel in Olde Naples! $925,000 Active

536 2nd ST S 536 NAPLES, Florida

2 Beds 2 Baths 1,210 SqFt

Timeless Old Florida charm defines this ideally located residence, positioned between the 3rd Street South and 5th Avenue South entertainment districts and just three blocks from iconic 5th Avenue South. This enchanting four bedroom plus den residence offers 2,909 square feet of living space, three full and one half baths, and a welcoming wraparound porch that sets the tone for relaxed coastal living. Tucked just off Cambier Park, the property features a thoughtfully connected two-story guest house with living space on the lower level and a private bedroom above—ideal as a primary suite, guest quarters, extended-family accommodation, or a private office retreat. The upper level of the main home showcases two bedrooms and a loft beneath a vintage tongue-and-groove wood-plank ceiling, with both bedrooms opening to private balconies that capture gentle coastal breezes. The main floor includes the kitchen and great room, along with a fourth bedroom or den with en-suite bath. Classic Old Florida storm shutters add both character and function. The generous backyard offers ample room for a pool and outdoor entertaining, while a rear-entry two-car garage off the paved alley provides convenience and additional parking. Private front and rear yards are framed by mature hedging, with a charming archway entry, quaint wooden gate, and parking for two vehicles off 8th Avenue South, plus additional parking in the rear. A 2019 metal roof adds peace of mind. Located directly across from Cambier Park, offering a competitive tennis program, shuffleboard courts and bocce, covered pavilion, band shell, and expansive green space. Close to everything, welcoming, and rich in character—this is a rare opportunity to own a true downtown Old Florida cottage. $3,500,000 Active

756 8th AVE S NAPLES, Florida

4 Beds 3 Baths 2,909 SqFt 0.17 Acres

Quietly situated at the southernmost end of Gulf Shore Boulevard South, directly across from beach access, this exceptional Olde Naples estate is a true crown jewel, spanning more than one-half acre. Designed by John Cooney of Stofft Cooney Architects and meticulously refurbished throughout, the residence reflects uncompromising craftsmanship and timeless sophistication and can be acquired turnkey furnished for immediate occupancy. From the moment of arrival, the home makes a lasting impression. Flickering gas lanterns, a gracious front porch, and classic symmetrical architecture accented by exquisite millwork create an inviting sense of elegance. Inside, refined finishes abound, including mahogany front doors, rift-sawn white oak flooring, and a striking vaulted ceiling detail upon entry. The living room’s balanced symmetry and detailed millwork flow seamlessly into the gourmet kitchen and dining area, anchored by a 60" Wolf dual-fuel range featuring six burners, an infrared charbroiler, and an infrared griddle. Additional highlights include a Sub-Zero side-by-side refrigerator and freezer, integrated refrigerator drawer systems, and two Miele dishwashers—perfectly suited for both everyday living and entertaining. Thoughtfully curated spaces throughout the home include a bespoke media room with soundproofed walls and a Savant sound system, a handsome study with custom built-in display cabinetry overlooking the pool, a fully reimagined bar and library, and a dedicated fitness studio complete with a steam shower—each space designed for both function and refined living. The estate is comprised of five well-appointed bedrooms, four of which feature en-suite baths, offering refined accommodations for both residents and guests alike. The Master Suite and Bath offer a true private retreat, enveloping you in comfort from head to toe. A tranquil sitting area overlooks the spa and pool, providing a serene backdrop for rest and reflection. Crown moldings and elegant casings throughout enhance the sense of refined craftsmanship, creating a space that feels like a peaceful escape—while remaining unmistakably at home. Following a complete renovation inside and out, the outdoor living spaces are equally compelling. An expansive, oversized porch is designed for rest and relaxation, offering an exceptional poolside setting framed by a preserved Wild Oak tree—an enchanting natural centerpiece that enhances the estate’s sense of serenity and timeless charm. Additional elevated improvements include two side-mounted car lifts, whole-house generator, dual dehumidification systems, a steam shower within the fitness studio underscoring the home’s exceptional level of care, resilience, and thoughtful investment. $22,500,000 Active

1963 Gulf Shore BLVD S NAPLES, Florida

6 Beds 8 Baths 9,047 SqFt 0.52 Acres

BRAND-NEW 2026-BUILT LUXURY ESTATE, JUST COMPLETED & NOT YET LIVED IN, PERFECTLY LOCATED IN OLDE NAPLES, APPROX HALF A MILE TO WORLD CLASS BEACHES & LESS THAN 1 MILE TO ICONIC 5TH AVE WITH WORLD-CLASS DINING, SHOPPING & ENTERTAINMENT! Enjoy highly coveted Western exposure for breathtaking sunsets, abundant natural light, and optimal sun over the pool. This modern contemporary masterpiece showcases a dramatic open floor plan with 4,730 square feet under air of bright, airy living space, featuring 4 bedrooms, 2 dens (one a loft/multi-purpose “family room”), 5 bathrooms, dual dining areas, dual laundry rooms, a 3-car garage, hurricane impact windows throughout, and a metal roof. Every detail has been thoughtfully curated—from oversized tile flooring and soaring ceilings with wood beam and shiplap accents to the modern wood-and-glass floating staircase and grand two-story entry foyer. The stunning chef’s kitchen is equipped with quartz countertops, sleek white cabinetry, warm wood accents, and an oversized walk-in pantry. Fully pocketing sliding glass doors create a seamless indoor-outdoor living experience. Step outside to your private resort-style oasis, featuring an expansive entertainment deck, large pool and spa, covered lounge area with an outdoor fireplace, and a summer kitchen. The luxurious primary suite is located on the main level and offers direct access to the pool deck, dual walk-in closets, and a spa-like bath with dual vanities, an oversized walk-in shower with dual entries, and a freestanding soaking tub. Upstairs, a loft-style cloud room with wet bar opens to a massive second-floor balcony, providing a private retreat ideal for entertaining or relaxation. Located within an A-rated Collier County school district and just minutes from Venetian Village, Waterside Shops, and Third Street South, this exceptional residence delivers the ultimate in luxury coastal living in one of Naples’ most sought-after neighborhoods. $6,999,000 Active

135 7th ST N NAPLES, Florida

4 Beds 5 Baths 4,730 SqFt 0.23 Acres

Awaken each morning to gentle Gulf breezes and the soothing rhythm of the surf in this thoughtfully designed Naples beachfront single-family residence. Tucked away at the end of a quiet lane, the home offers a spacious multiple level floor plan, convenient two car direct access garage, a private 3-floor elevator, and abundant storage. The primary living suites stretch majestically along the shoreline, capturing mesmerizing, unobstructed views of the Gulf, its crystalline coastline, and beautiful sunsets in the evening. Designed for relaxed coastal living and effortless entertaining, the open kitchen flows seamlessly into the great room where floor-to-ceiling sliding glass doors dissolve the boundary between indoors and out, opening to a covered balcony overlooking the beach. Hosting family and friends is a pleasure with well-appointed en suite guest bedrooms and endless outdoor activities at the beach or pool or on the expansive lawn. After a day at the sandy beach, rinse off and enjoy a refreshing dip in the pool before retreating to the comfort of the primary suites inside this lovely home. Perfectly positioned to offer both privacy and convenience, the residence is just moments from Naples’ renowned shopping and fine dining on 5th Avenue, allowing you to enjoy the best of coastal living without the compromise of walkability. This ideal beachfront home presents endless opportunities for personalized, easy living. It is truly a rare offering, and it is a once in a lifetime chance to own the sunset! $14,000,000 Active

25 2nd AVE S NAPLES, Florida

3 Beds 4 Baths 3,819 SqFt 0.24 Acres

This 2022 custom-built home in Old Naples offers the perfect blend of luxury and resilience in an unbeatable location—just steps from NCH Baker Hospital, 5th Avenue South, and the beach.Transitional cottage-style residence with nearly 5,000 sq. ft. of air-conditioned living space, featuring 5 en-suite bedrooms (including a private guest cabana), a dedicated study, gourmet kitchen, wide-plank wood floors, and a spacious fenced backyard.Enjoy the saltwater pool and spa, covered outdoor kitchen, and fireplace—all elevated by concrete construction, natural gas, and impact glass.A rare opportunity to own an elegant, storm-ready coastal retreat in the heart of Old Naples. $7,500,000 Active

739 5th AVE N NAPLES, Florida

5 Beds 9 Baths 4,825 SqFt 0.24 Acres

VIEW ALL OLDE NAPLES PROPERTIES

Dining, Shopping and Entertainment Near Olde Naples

Olde Naples is home to the Third Street South and Fifth Avenue shopping centers, both upscale experiences featuring high-end retailers. It’s also home to some of the city’s best restaurants, including The Boathouse on Naples Bay, The Claw Bar, Seventh South Craft Food + Drink and Campiello. You’ll find a wide range of dining options, from fast-and-fresh places where you can grab a salad to go to award-winning fine dining.

There’s always something to do in Olde Naples, whether you want to spend a few hours reading a book at your favorite café, lounging on the beach or exploring art galleries (two of the most popular are Sheldon Fine Art and the Gardner Colby Gallery). The Naples Yacht Club, Olde Cypress Golf Course, and a number of country clubs, tennis clubs and other amenities are located inside or just outside the community.

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Drive Times From Olde Naples

Olde Naples is in a very convenient location on the Gulf. This one-of-a-kind community is:

Golf Courses Near Olde Naples

The Olde Cypress Golf Course is at the border of the Olde Naples area, and there are several golf and country clubs near the community. Some of the most popular among locals include Wilderness Country Club, Royal Poinciana Golf Club, Naples Grande Golf Club, Foxfire Country Club and the Lakewood Country Club.

Public Parks Near Olde Naples

Cambier Park, Baker Park and Rodgers Park are all within a short jaunt from Olde Naples. Some of the other popular parks, many of which offer playgrounds, volleyball courts and basketball courts, and even space for dogs to run off-leash include Veterans Memorial Park, Charlie C. Anthony Park and the River Park Playground, as well as Merrihue Minim Park, Sugden Regional park and the Naples Dog Park.

Retiring in Olde Naples

Olde Naples is an excellent place to retire due to its proximity to all the amenities you need. Whether you’re a golfer, an avid shopper or a foodie, there’s something for you within a short distance from the Olde Naples community. You’ll find banks, physicians’ offices, dental practices, grocery stores and so much more within a quick drive from your front door if you retire in Olde Naples.

Olde Naples History

Olde Naples is the city of Naples’ historic district. In the early 1930s, winter visitors started coming to the area to warm up and enjoy the sun, sand and spray. A small golf course was located at the end of  Fifth Avenue, right near the beach, and Charles Lindbergh used to stop by the area to pick up supplies on his way to and from his retreat in Sanibel.

The downtown area had only a few businesses at that time, as most people were just passing through on the then-new Tamiami Trial. However, as hotels began to spring up over the years, Olde Naples grew in popularity – and so did the other communities nearby.

Please contact us today to learn more about Olde Naples Real Estate or Naples’ luxury lifestyle and offerings. Talk to you soon!

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OLDE NAPLES MARKET TRENDS

TRENDS

Click on the “VIEW Market Report” button to the right to view more statistics about the Olde Naples Real Estate Market including average selling price, number of active homes, recently sold properties, demographics and to subscribe to have updated reports sent to your email each month!

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