Olde Naples Homes with Circular Driveway Parking features

Welcome to Olde Naples, a timeless gem nestled in the heart of Naples, Florida. This enchanting subdivision is renowned for its rich history, charming architecture, and vibrant lifestyle, making it a coveted destination for those seeking the perfect blend of luxury and comfort. With its picturesque streets lined with lush palm trees and stunning coastal scenery, Olde Naples embodies the quintessential Florida experience.

One of the standout features of homes in this delightful community is the presence of circular driveways. These elegant parking solutions not only enhance the curb appeal of each residence but also provide convenience for homeowners and guests alike. Imagine arriving home to a beautifully landscaped property where your vehicle can be parked with ease, allowing for smooth transitions in and out of your driveway. Circular driveways are a hallmark of Olde Naples, reflecting the sophistication and thoughtful design that characterize this neighborhood.

Residents of Olde Naples enjoy a lifestyle filled with leisure and recreation. The proximity to pristine beaches, upscale dining options, and boutique shopping creates an idyllic environment for relaxation and entertainment. Whether you’re taking a leisurely stroll along the historic streets or indulging in the vibrant local culture, Olde Naples offers a unique charm that captivates all who visit.

In this enchanting subdivision, you’ll find a variety of homes that embody elegance and comfort, each with its own unique character. Experience the allure of Olde Naples, where every day feels like a vacation, and the beauty of Florida living awaits you. Come discover your dream home in this captivating community!

Newest Olde Naples Homes with Circular Driveway Parking features

$6,450,000

4 Beds ⋅ 4.5 Baths ⋅ 226019479 MLS

PRICED AT LAND VALUE! LOWEST PRICED LISTING ON THE BEACH BLOCK IN ALL OF OLDE NAPLES — (Optional 50’ boat slip at the Cove Inn available for purchase with the property.) Opportunity knocks for a chance to own the ultimate beach cottage in one of Naples’ most coveted locations, just steps from the iconic Naples Pier and the white sugar-sand beaches of the Gulf. Privately tucked within lush tropical landscaping, this one-of-a-kind “Swiss-Family Robinson Treehouse” blends artistic charm with modern comforts, creating a secluded retreat in the heart of Olde Naples. Just a short stroll from the boutiques, fine dining, farmers markets, local parades and vibrant coastal lifestyle of 3rd Street South, the setting simply cannot be replicated. Designed for both relaxation and entertaining, the property showcases an incredible collection of unique indoor and outdoor spaces, including a heated swimming pool, private courtyard oasis, detached bar house with full kitchen, tranquil koi pond, infrared sauna, outdoor shower, and a raised covered “widow’s watch” seating area perfect for enjoying Naples sunsets, firework shows and coastal breezes. Additional highlights include a durable metal roof, back-alley access, oversized driveway for 5+ vehicles, and exceptional privacy throughout the property. Situated on a 77’ x 151’ lot, the possibilities are endless. Whether you envision renovating and enjoying the existing residence, creating a luxury custom estate, or developing a high-end investment property, this homesite offers extraordinary potential in a premier beach-block location right in the action of downtown Naples. Investors will appreciate the strong vacation rental and spec-home opportunities, while end users can create the ultimate private beach retreat just a few steps from the Gulf of Mexico. Adding to the long-term appeal, the newly reimagined Naples Pier is nearing completion, further enhancing the value and desirability of this exceptional location. A rare offering with unmatched character, location, and future potential — this is Olde Naples living at its finest. High and dry with no flooding waters entering the main residence.

61 12th AVE S, Naples

$2,593,000

3 Beds ⋅ 3 Baths ⋅ 226014309 MLS

Prime Olde Naples homesite on a quiet Broad Ct S street, offering southern rear exposure and desirable "high and dry" X500 elevation. This 74’ x 115’ interior lot provides flexibility for future design and construction while allowing immediate enjoyment of the existing residence. The property’s location supports convenient access to nearby beaches, downtown shopping, dining, and cultural amenities. Alley access enhances future architectural possibilities, including garage placement and courtyard configurations. Mature landscaping and a private setting create a comfortable environment today, with fine opportunity for redevelopment. Whether planning a new residence or seeking an Olde Naples location with immediate usability, this property offers a balanced opportunity combining elevation, exposure, and neighborhood setting. Compare this lot with other Old Naples land or redevelopment offerings.

778 Broad CT 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

$6,495,000

4 Beds ⋅ 5 Baths ⋅ 225071448 MLS

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.

135 7th ST N, Naples

$12,995,000

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

$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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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.