Olde Naples Homes with Circular Driveway Parking Features

Welcome to Olde Naples, a charming neighborhood that perfectly encapsulates the allure of coastal living in sunny Florida. Nestled within the picturesque city of Naples in Collier County, Olde Naples is renowned for its stunning blend of historic charm and modern sophistication. As you stroll through the tree-lined streets, you’ll be captivated by the beautifully preserved architecture, vibrant gardens, and the inviting atmosphere that makes this community a true gem.

One of the standout features of homes in Olde Naples is the elegant circular driveway parking, a hallmark of luxurious living. These thoughtfully designed driveways not only enhance the curb appeal of the residences but also provide convenience and ease for homeowners and guests alike. Imagine arriving at your stunning abode, where the circular driveway welcomes you with open arms, allowing for effortless entry and exit. It’s a perfect blend of functionality and aesthetic charm, ideal for entertaining friends or simply enjoying a quiet evening at home.

Beyond the exquisite homes, Olde Naples boasts proximity to pristine beaches, upscale boutiques, and gourmet dining options, making it a lifestyle destination for those who appreciate the finer things in life. Whether you’re exploring the vibrant local art scene or indulging in a sunset stroll along the shoreline, Olde Naples offers a unique blend of relaxation and sophistication.

Discover the magic of Olde Naples, where every day feels like a vacation, and your dream home awaits.

Newest Olde Naples Homes with Circular Driveway Parking Features

$6,100,000

4 Beds ⋅ 3.5 Baths ⋅ 226031446 MLS

Four blocks to the beach in the heart of Olde Naples, this fully renovated residence delivers the rare combination of location, structural integrity, and turnkey modern comfort. Built of concrete block on both levels and located in the desirable X500 flood zone, the home has been thoughtfully upgraded for both peace of mind and everyday luxury. A new 2025 standing-seam aluminum roof, impact windows and doors, provide storm-ready confidence, while a southern-exposure fills the interior with natural light. Designed for effortless living and entertaining, the open floor plan centers around a chef’s kitchen appointed with Wolf and Sub-Zero appliances, custom cabinetry, and island seating. The great room flows seamlessly to a private yard retreat featuring a heated saltwater pool with Pentair automation, new heater and chiller for year-round enjoyment. The first-floor primary suite offers privacy and ease, complemented by beautifully updated baths and refined finishes throughout. Upstairs, a spacious loft and guest suites open to a balcony overlooking the pool courtyard—ideal for visitors or multigenerational living. Additional features include a two-car garage, storage, updated mechanical systems, and close proximity to 5th Ave, 3rd St, the Naples Pier, and Gulf beaches. For buyers seeking an Olde Naples home that lives meticulously like new—with modern systems, elevated construction, and true walkability—this property represents a compelling opportunity in one of Naples’ most desirable neighborhoods.

570 2nd AVE N, Naples

$13,500,000

5 Beds ⋅ 6.5 Baths ⋅ 226029919 MLS

Everyone Stops to Take a Picture. There are homes you walk past—and then there are homes that make you stop. Just one house from the beach in the heart of downtown Naples, this exceptional residence has become one of those unmistakable properties that catches the eye of nearly everyone who passes. People stop, admire it, and more often than not, take a picture. Inspired by the owners’ travels throughout the Mediterranean, the architecture is romantic, distinctive and beautifully detailed. At first glance, stately wrought-iron gates crowned with a pineapple finial welcome you to the property. Beyond them, twin limestone staircases gracefully sweep from either side toward the grand front entrance, creating an unforgettable sense of arrival. Look closer and the details become even more captivating: Juliet-style wrought-iron flower boxes, graceful fanlight transoms, open-air terraces, limestone accents and architectural elements reminiscent of a European villa. Then the grand front door opens to a dramatic foyer soaring 24 feet above—revealing that the magnificence of the exterior is only the beginning. It is a first impression you simply don’t forget. No wonder everyone stops to take a picture.

40 5th AVE S, Naples

$6,900,000

3 Beds ⋅ 3.5 Baths ⋅ 225075505 MLS

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.

2080 Gordon DR, Naples

$12,500,000

5 Beds ⋅ 7.5 Baths ⋅ 226002046 MLS

A landmark, custom built, Old Naples estate just four homes from the Gulf. Elevated and recently renovated, this exceptional residence offers over 7,500 square feet of refined AC-living with timeless architecture and exquisite craftsmanship. Features include a grand two-story foyer, coffered ceilings, rich millwork, library, formal dining, and expansive living spaces filled with natural light. The chef’s kitchen boasts Wolf and Sub-Zero appliances, dual islands, marble prep areas, butler’s pantry, and wine cellar. The luxurious master suite offers a sitting area, dual walk-in closets, spa bath, and private balcony. Outdoor living includes a heated, salt system pool and spa, outdoor kitchen, fireplace, lush landscaping, and shaded entertaining areas. Rare, air-conditioned garage for 10+ vehicles, impact windows and doors, private elevator, and generator. High and dry, moments to beaches, dining, and shopping—this is Old Naples luxury at its finest.

140 3rd AVE S, Naples

$9,900,000

5 Beds ⋅ 5.5 Baths ⋅ 225078983 MLS

One block from the beach and two blocks from the fine dining and boutiques of historic Third Street South. An exceptional all-concrete custom home crafted by Grand Bay Development that embodies the best of Naples' luxury living. Built to a 15 foot elevation for peace of mind. Featuring 5 bedrooms, 2 dens, plus a flex room off of the pool area and 5 & 1/2 bathrooms. Every detail reflects a commitment to world-class design and craftsmanship, from the curated global finishes to the tropical connection between indoor and outdoor living. Updated in 2021 with new HVAC's, beautiful wall coverings and finishes as well as a gourmet kitchen adorned with Cristallo Quartzite serving as the heart of the home, with beautiful hardwoods that are increasingly rare, and surrounded by spectacular greenery that creates a sense of privacy and retreat. A custom wet bar with agate stonework opens to the elegant great room, where walls of glass frame western facing terraces. The primary suite offers an elevated sense of serenity with a private balcony. A rooftop deck not to be rivaled provides panoramic views of the coastline, breathtaking sunsets, and the Naples skyline. The southern facing lanai features a vanishing-edge saltwater pool, expansive covered entertaining areas protected by screens and shutters, and meticulously designed tropical landscaping. Combining architectural integrity, global inspiration, and an unmatched location, this residence defines a warm and inviting luxury along the Naples coast.

1441 Gulf Shore BLVD S, Naples

$17,950,000

5 Beds ⋅ 7.5 Baths ⋅ 225073939 MLS

Step into refined coastal living with this exceptional new construction home located just two blocks from the beach in the heart of Olde Naples. Designed by Stofft Cooney Architects, built by Equinox Construction Group, and styled by Freestyle Interior Design, this residence blends timeless elegance with modern functionality. The spacious great room floor plan invites seamless indoor-outdoor living, ideal for both relaxed family life and sophisticated entertaining. A chef’s kitchen equipped with premium appliances and a separate prep kitchen offers versatility for everyday meals or catered gatherings. The home features five bedrooms, five full baths, and three half baths, including two luxurious master suites, one on each level, providing privacy and flexibility for family and guests. Additional spaces include a club room, two laundry rooms, and thoughtfully designed living areas throughout. A three-car garage with alley access preserves the classic charm of the front facade while adding convenience. With white oak wood flooring, high-end finishes, a whole-house generator, and an unbeatable location in one of Naples’ most coveted neighborhoods, this property presents a rare opportunity to enjoy brand-new luxury living just moments from the Gulf of Mexico.

285 Central AVE, Naples

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