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 true beach bungalow in the heart of Old Naples, this charming three-bedroom, two-bath residence sits on an expansive 150-by-100-foot corner lot just three blocks from the Gulf. Surrounded by mature trees and lush landscaping, the property offers a wonderful sense of privacy while capturing the relaxed, timeless character of coastal Naples.The home is filled with natural light and offers inviting indoor-outdoor living, providing an opportunity to enjoy the property as it is, thoughtfully reimagine the existing residence, or take advantage of the generous homesite to create a new custom home.Ideally located at the corner of Third Street North and Fourth Avenue North, 444 Third Street North places the beach, Fifth Avenue South and Third Street South all within easy reach.

$5,950,000 Active

444 3rd ST N NAPLES, Florida

3 Beds 3 Baths 1,860 SqFt 0.36 Acres

This Old Naples Dolphin Cottage was built in 1935 and has been meticulously restored to reflect the owner's love of historic Old Naples. The home is a blend of classic and fresh design ideas, with tongue and groove ceilings, wide plank wood flooring and updated baths that are aglow with vibrant and classic colors. The rear porch that overlooks the freeform pool and lushly landscaped rear yard is a comfortable oasis to relax and unwind after a long day enjoying all Naples has to offer. Naples pristine beaches and the world-class dining and nightlife of Third Street South are just a short distance away. A unique home that brings you back to a bygone era and timeless charm of Old Naples.

$5,299,000 Active

244 11th AVE S NAPLES, Florida

3 Beds 2 Baths 1,699 SqFt 0.172 Acres

This home feels like a big hug! Just the right amount of indoor and outdoor living. Very private with Clusia and Podocarpus hedges surrounding the property for maximum privacy. A perfect retreat for individuals, family and friends. As you enter the home you are greeted by white washed wood flooring, open Great Room with volume ceilings that lead to a custom Cupola that reaches 26', to add light and architectural detail. Dining space that can easily seat 10-12 people, and bar area with a beverage refrigerator and wine/glass storage. The cook's kitchen features a large island (seating 6), ample storage and gas cooktop. Six sets of French doors open to the outdoor living areas, including a living/kitchen space with a gas grill and fireplace, along with a large covered lanai for entertaining and alfresco dining. The saltwater pool includes a spa and sun shelf. Primary suite has a spa like bath and two walk-in closets. From the bed and sitting area there are lovely views of the gardens and pool. This residence is situated on one of Old Naples most coveted and beautiful streets. There is a large side yard on the south side of the home perfect for outdoor games, reading, dogs, kids and/or grandkids. A quick walk to the beach, Fifth Avenue dining and shopping, NCH and so much more. The garage is situated off the alley with additional parking, along with a circular drive off of 3rd Street.

$6,500,000 Active

131 3rd ST N NAPLES, Florida

5 Beds 4 Baths 3,923 SqFt 0.34 Acres

One or more photo(s) has been virtually staged, AI generated or rendered. Six doors from the Gulf, exceptional single-level living in the heart of Old Naples. Set on a generous one-third-acre homesite along a quiet residential street, 185 North Lake Drive offers a contemporary way of living that is increasingly difficult to recreate. While much of today’s new construction reaches vertically, this thoughtfully designed residence lives entirely on one level, with soaring ceilings, abundant natural light and an effortless connection between indoors and out.At the heart of the home, a magazine-worthy kitchen makes a dramatic statement with a counter-to-ceiling ombré mosaic backsplash, sculptural hood and professional-grade Wolf appliances. The open great room flows naturally to the dining and family areas, while zero-corner sliders extend the living spaces to an expansive covered lanai.Designed for year-round entertaining, the outdoor living experience includes a fully equipped summer kitchen, bar and alfresco dining, custom-detailed ceilings, fireplace, generous lounge areas, and an elevated pool and integrated spa surrounded by lush privacy landscaping.The spacious primary suite offers room for a private office or sitting area and a serene, spa-inspired bath with freestanding tub, oversized multi-head shower, dual vanities and private water closet. Generously proportioned guest accommodations include a suite that lives like a second primary, with a walk-in closet and private outdoor access.Beyond the residence itself is the lifestyle that makes this location extraordinary. Stroll to the end of the block for sunset on the Gulf, enjoy cocktails at HB’s at Four Seasons Naples Beach Club, dinner on Fifth Avenue South, or the Farmers Market on Third Street South, then return to the privacy of North Lake Drive.Offered move-in ready and turnkey furnished, with an attached three-car garage, everything is already in place to enjoy the season ahead, without the wait of building or the task of furnishing a new home.A distinctive opportunity to enjoy the very best of Old Naples, six doors from the Gulf, beautifully private and entirely on one level.

$7,499,000 Active

185 North Lake DR NAPLES, Florida

4 Beds 6 Baths 4,082 SqFt 0.33 Acres

$6,495,000 Active

135 7th ST N NAPLES, Florida

4 Beds 5 Baths 4,730 SqFt 0.23 Acres

Ideally located in the heart of Olde Naples, just three blocks from the Gulf, this striking contemporary residence pairs innovative architectural design with exceptional finishes and effortless indoor/outdoor living. Set along one of Olde Naples’ most picturesque streets, north of Central Avenue and surrounded exclusively by single family homes, the property enjoys a lush, private setting with the added convenience of alley access. Built by respected luxury homebuilder Build., the residence showcases exceptional craftsmanship and thoughtful design throughout. Southern exposure fills the interiors with natural light, while soaring ceilings and expansive walls of glass create a bright, open atmosphere. The great room flows seamlessly to the outdoor living areas, creating an ideal setting for both everyday living and entertaining. The chef’s kitchen features sleek Italian cabinetry, premium Miele and Liebherr appliances, a built in coffee system, wine refrigeration, and an oversized island. Upstairs, the spacious primary suite offers a spa inspired bath with a freestanding soaking tub, oversized shower, and private outdoor shower. Three additional guest suites, each with an en-suite bath, provide comfortable and private accommodations for family and guests. Outside, the resort style pool and spa feature cascading water elements, a sun shelf, and LED lighting, all surrounded by lush landscaping for exceptional privacy. The covered lanai is designed for year-round entertaining with an outdoor kitchen, built in grill and refrigerator, roll down screens, fireplace, fire pit, and media lounge. A refined Olde Naples residence offering distinctive architecture, exceptional craftsmanship, and an outstanding location just moments from the Gulf, beaches, dining, and shopping.

$8,250,000 Active

376 1ST AVE N NAPLES, Florida

4 Beds 5 Baths 3,768 SqFt 0.23 Acres

In the heart of Old Naples, just three blocks from famed Fifth Avenue South and a short distance from the beach, this nearly new residence, constructed by Gulfstream Homes in 2025, captures the timeless charm of a classic Naples cottage while delivering the craftsmanship, sophistication and conveniences of a modern luxury home. Offered beautifully furnished, the residence feels distinctly at home among the enchanting streets of Olde Naples, with coastal architecture and thoughtful details creating an elegant sense of place from the moment you arrive. Inside, every square inch has been thoughtfully maximized for effortless resort-style living. The light-filled great room is wrapped in windows and opens seamlessly to the outdoor living areas, while warm wood flooring, detailed millwork and a beautifully crafted ceiling bring character and dimension. At the center of the home, a chef's kitchen pairs timeless cabinetry with an expansive island, gas cooking and Thermador appliances. A dedicated coffee bar and impressive butler's pantry elevate everyday living with an ice maker, second dishwasher and refrigerated beverage drawers. The adjoining dining area is designed equally for intimate dinners and lively gatherings, anchored by a dramatic bar feature wall with a full-size wine refrigerator and separate beverage refrigerator. Nearly every main living space is connected visually and physically to the home's sparkling pool and spa, creating the relaxed indoor-outdoor lifestyle for which Naples is celebrated. A bright, inviting sundeck extends along the side of the residence, and a charming side yard with a turf putting green adds another unexpected element of recreation. The first-floor primary suite is a serene, light-filled retreat, beautifully finished with a luxurious bath featuring a freestanding soaking tub, oversized shower and generous walk-in closet. Upstairs, guests enjoy an exceptional level of privacy with two beautifully appointed en-suite bedrooms, a second primary suite with a spa-inspired bath, a dedicated den and a charming bunk room with accommodations for four. A second-floor washer and dryer adds thoughtful convenience for family and guests. Completing the residence is an oversized two-car garage with generous ceiling height and room for vehicle lifts, plus a full-home generator. With its combination of classic Old Naples architecture, nearly new construction, sophisticated furnishings and incredible location, this exceptional residence offers the rare opportunity to enjoy the character of a timeless coastal cottage without compromising the luxuries of a thoughtfully designed modern home.

$6,290,000 Active

844 8th ST S NAPLES, Florida

4 Beds 5 Baths 3,495 SqFt 0.15 Acres

Rare opportunity in the heart of Olde Naples. Ideally positioned between Fifth Avenue South and historic Third Street South, this expansive 128' x 150' lot offers a rare opportunity to build a remarkable new residence in one of Olde Naples’ most desirable locations. Enjoy equal walking distance to Fifth Avenue South and Third Street South, with the Gulf, Naples Pier, Cambier Park, The Dock, Tin City, and many of downtown Naples’ most popular destinations all nearby.The generous lot dimensions, central location, and exceptional walkability create an outstanding setting for a thoughtfully designed new residence. The property may also offer the potential for a future lot split, creating additional redevelopment possibilities, subject to applicable approvals. Whether envisioned as a sophisticated coastal retreat or an impressive full-time residence, the property offers the space and setting to bring a distinctive vision to life while enjoying everything Olde Naples has to offer just moments away.The property is currently improved with a concrete block duplex-style residence and additional cottages, offering flexibility while planning for its future. A unique opportunity to build or redevelop on an exceptionally sized lot in the very center of Olde Naples.

$6,250,000 Active

560 9th AVE S NAPLES, Florida

4 Beds 4 Baths 2,182 SqFt 0.44 Acres

One or more photo(s) has been virtually staged, AI generated or rendered. Set along one of Old Naples’ quiet, palm-lined streets and just a short stroll from the Gulf and Third Street South, 835 11th Avenue South presents modern craftsmanship with timeless design. Built by Lotus Construction, in collaboration with MHK Architecture and Freestyle Interiors, the home reflects a thoughtful approach to scale, proportion, and livability rather than excess. The residence spans more than 4,700 square feet of interior living space and is arranged to support both privacy and connection, offering four ensuite bedrooms and six bathrooms featuring Neorest Toto toilets. On the main floor, the primary suite is intentionally positioned for convenience and discretion, featuring a spa-inspired bath with a soaking tub, glass-enclosed shower, floating dual vanities, and a private water closet. The heart of the home is defined by soaring ceilings, abundant natural light, and a calm material palette. Wide-plank white oak flooring, tailored millwork, and soft neutral tones establish a refined backdrop for daily life. The kitchen is both elegant and highly functional, outfitted with integrated refrigeration, dual wall ovens, concealed storage, and streamlined cabinetry that transitions seamlessly into the dining and great room. Large hurricane-impact sliding doors open the interior to the outdoor living area, creating an effortless indoor-outdoor connection. A thoughtfully finished elevator provides smooth access between levels. Upstairs, a private VIP suite offers exceptional flexibility, complete with its own living area, full bath, and two balconies—well suited for extended guests or multi-generational living. Two additional guest suites and a dedicated laundry room complete the upper level, and a home generator is in place for additional peace of mind. Outdoors, the rear courtyard is designed for relaxed entertaining, centered around a custom pool and spa, covered lounge, full outdoor kitchen, and pool bath. The setting is private and quiet, enhanced by alley access. A three-car garage—an uncommon amenity in Old Naples—features extra ceiling height suitable for vehicle lifts or specialized storage. Just blocks from Naples’ most celebrated dining, boutiques, and cultural destinations, this home delivers a rare combination of architectural discipline, location, and immediate enjoyment. It is a residence defined by enduring quality and thoughtful design—crafted to be appreciated long after the first impression.

$8,995,000 Active

835 11TH AVE S NAPLES, Florida

4 Beds 6 Baths 4,709 SqFt 0.17 Acres

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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:

2 miles from Coquina Sands
3 miles from Moorings
3 miles from Port Royal
5 miles from Park Shore
6 miles from Grey Oaks
7 miles from Pelican Bay
7 miles from Pine Ridge
9 miles from Tiburón
10 miles from Pelican Marsh
10 miles from Vanderbilt Beach

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

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