Olde Naples Homes with Courtyard Exterior Features

Welcome to Olde Naples, a charming and sophisticated subdivision nestled in the heart of Naples, Florida. Renowned for its picturesque streets and historic ambiance, Olde Naples offers a unique blend of coastal elegance and timeless charm. Just a stone’s throw from the stunning Gulf of Mexico, this area boasts an enviable location that allows residents to enjoy the best of Florida living.

Olde Naples is characterized by its lush, tropical landscapes and beautiful architecture, making it a coveted destination for those seeking a vibrant community. The neighborhood is home to a variety of exquisite properties, many of which feature stunning courtyard exterior designs. These thoughtfully crafted homes create a private oasis, ideal for relaxation and entertaining. Imagine stepping through your front door into a serene courtyard adorned with lush greenery and vibrant flowers, providing a tranquil escape right at your fingertips.

The allure of Olde Naples extends beyond its stunning homes; residents enjoy easy access to world-class dining, upscale shopping, and picturesque beaches. Stroll along the famous Fifth Avenue South, where you can find charming boutiques and gourmet restaurants, or take a leisurely walk to the pristine shores of Naples Beach, where sunsets paint the sky in breathtaking hues.

Whether you're looking for a seasonal getaway or a permanent residence, Olde Naples offers an unparalleled lifestyle that combines luxury, comfort, and a strong sense of community. Discover the magic of Olde Naples and experience the charm of courtyard living in this idyllic Florida paradise.

Newest Olde Naples Homes with Courtyard Exterior Features

$6,795,000

3 Beds ⋅ 4.5 Baths ⋅ 226038580 MLS

A private sanctuary of timeless elegance, where thoughtful architecture and tranquil outdoor living come together in one of Old Naples’ most desirable settings. Custom-built by Waterside Builders for its original owners, this beautifully appointed residence offers three bedrooms plus a den, blending sophisticated design with effortless coastal comfort. Refined interiors and inviting living spaces create an atmosphere of understated elegance throughout. Two distinct outdoor living areas offer exceptional opportunities for relaxation and entertaining, complemented by a peaceful pool setting that serves as a private retreat surrounded by tropical beauty. An air-conditioned three-car garage, discreetly accessed from the rear alley, provides exceptional convenience while preserving the home's attractive streetscape. Ideally on a high-and-dry homesite within Flood Zone X500, outside the high-risk Special Flood Hazard Area, this exceptional property offers an additional measure of peace of mind. Located along coveted First Avenue North, the residence provides convenient access to Naples’ pristine beaches, world-class dining and the celebrated boutiques of Fifth Avenue South and Third Street South. A distinctive opportunity to experience the charm, privacy and effortless lifestyle of Old Naples.

530 1st Ave N, Naples

$25,900,000

6 Beds ⋅ 11.5 Baths ⋅ 226035214 MLS

NOW COMPLETE! Commanding a rare western lakefront setting in the heart of Old Naples, this extraordinary new construction estate represents an exceptional achievement in architecture, craftsmanship and sophisticated resort-style living. Encompassing more than 9,400 square feet of interior living space, the residence was conceived as a private retreat where dramatic design and meticulous attention to detail come together effortlessly. Twin infinity-edge reflecting pools create a striking arrival, leading into a soaring two-story great room defined by precision millwork, architectural symmetry and a sculptural floating staircase. The formal dining room is enhanced by a dramatic glass-enclosed wine wall incorporated into bespoke cabinetry, while the chef’s kitchen features Wolf and Sub-Zero appliances, dual Miele coffee stations and a concealed butler’s pantry designed for seamless entertaining. The first-floor primary suite is a private sanctuary unto itself, complete with a dedicated study, two expansive dressing rooms, discreet laundry center and luxurious marble-clad bath with indoor and outdoor showers. Upstairs, five beautifully appointed bedroom suites are joined by a media lounge and concealed club room featuring a full bar and humidor. Equally impressive outdoor spaces were designed to showcase the spectacular western lake views and Naples sunsets. A 60-foot negative-edge pool spans the rear of the residence, with dramatic stepping-stones crossing the water to a sunken firepit lounge. An elevated spa, expansive covered loggia and fully equipped summer kitchen create an extraordinary setting for outdoor living and entertaining. A detached fitness pavilion overlooking the lake provides another remarkable element to this private resort environment. Additional features include an elevator, three laundry stations, commercial-grade sheet ironer, whole-home 60kW generator, comprehensive smart-home technology and a five-car split garage designed with the collector in mind. Created by EMB Custom Homes in collaboration with MHK Architecture, Lotus Construction and Freestyle Interiors, and offered fully furnished, this newly completed lakefront estate presents a rare opportunity to experience exceptional scale, design and craftsmanship in one of Old Naples’ most coveted settings.

616 BOUGAINVILLEA RD, Naples

$6,250,000

4 Beds ⋅ 4 Baths ⋅ 226031870 MLS

One or more photo(s) has been virtually staged, AI generated or rendered. 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.

560 9th AVE S, Naples

$4,475,000

3 Beds ⋅ 3.5 Baths ⋅ 226031335 MLS

Between the Gulf of Mexico and Naples Bay, this coastal contemporary home captures the charm of Old Florida living. Just six blocks to the beach and Naples Pier, and moments from 3rd Street South and 5th Avenue, it’s perfectly situated for the Olde Naples lifestyle. Filled with natural light, the home features 3 bedrooms plus a den, 3.5 baths, a gourmet kitchen, dining area, morning nook, and custom elevator. French doors open to rich wood floors and custom ceilings. Outdoor spaces include a front porch, second floor balcony, covered lanai, heated pool and spa, and lush tropical landscaping for privacy. Built to modern standards with impact windows, a whole-house generator, new A/C, and elevated construction that’s remained high and dry—this residence offers timeless coastal style and enduring quality in an exceptional location.

645 Broad AVE S, Naples

$4,499,000

5 Beds ⋅ 5.5 Baths ⋅ 226025231 MLS

Exceptional Olde Naples living in the heart of it all. Ideally located just 5 blocks from Historic Fifth Avenue South, 8 blocks from Third Street South, and minutes to the City Dock, lovely park overlooking the bay across the street, 888 10th Avenue South offers a sophisticated blend of luxury, comfort, and effortless coastal living. The spacious residence features four bedrooms in the main house plus a private guest cabana above the garage, providing an ideal setting for family and guests. Soaring 11-foot ceilings, Legno Bastone flooring, UMI quartz countertops, and a Thermador Professional Series kitchen showcase the home's elevated finishes. Generously sized primary suites and laundry facilities on both levels add exceptional functionality. The outdoor living spaces are designed for quintessential Naples entertaining, with a fully equipped outdoor kitchen, grilling area, gas fireplace, retractable screens, and sun deck surrounding the beautiful pool and raised spa. Three additional balconies offer glimpses of Naples Bay and the surrounding area. A rare opportunity to enjoy the privacy and comfort of a refined Olde Naples residence within easy walking distance of the very best of downtown Naples.

888 10th AVE S, Naples

$6,150,000

4 Beds ⋅ 5.5 Baths ⋅ 226024974 MLS

TWO EXCEPTIONAL OPPORTUNITIES. ONE EXTRAORDINARY ADDRESS. Perfectly positioned in the heart of Old Naples, this beautifully reimagined residence offers a rare opportunity to embrace today's luxury lifestyle while investing in tomorrow's possibilities. Just moments from the Gulf beaches, Fifth Avenue South, Third Street South, and the exciting transformation reshaping Downtown Naples, this exceptional property appeals to two distinct buyers: those seeking a sophisticated, move-in-ready luxury home and those who recognize the extraordinary long-term value of one of Old Naples' premier homesites. Thoughtfully reconstructed and beautifully updated, the home blends timeless coastal elegance with comfortable everyday living. Expansive open-concept gathering spaces flow effortlessly from the gourmet kitchen to the indoor and outdoor living areas, creating the perfect setting for everything from intimate family dinners to large-scale entertaining. A private upstairs guest retreat offers exceptional flexibility for extended family, visiting guests, or a secluded home office, while every space has been designed with both comfort and functionality in mind. Equally impressive is the outdoor setting. Unlike many Old Naples properties where the home occupies nearly the entire lot, this residence offers a southern-exposure backyard with room to truly enjoy the Florida lifestyle. Relax beside the pool and spa, envision a custom outdoor kitchen, entertain beneath the stars, or simply enjoy the rare open green space for children, grandchildren, or pets to play. Beyond the property itself lies one of its most compelling attributes; its location at the center of the next chapter of Old Naples. As remarkable new luxury developments, elevated hospitality experiences, world-class dining, boutique shopping, and exciting new destinations continue to redefine the downtown landscape, this already coveted neighborhood is becoming even more desirable. More than simply acquiring a beautiful home, you're investing in one of Old Naples' most coveted locations—offering the rare opportunity to enjoy TWO EXCEPTIONAL OPPORTUNITIES. ONE EXTRAORDINARY ADDRESS.

742 11th AVE S, Naples

$1,870,000

2 Beds ⋅ 2 Baths ⋅ 226027036 MLS ⋅ Olde Naples BLDG.

Experience the pinnacle of downtown living at 365 5th Ave S, Unit 307, where the vibrant energy of Naples meets sophisticated coastal elegance. Located right in the heart of the iconic 5th Avenue South district and only two blocks from the beach, this residence places world-class dining, high-end boutiques, and sugar-sand beaches just moments from your front door. In the heart of the action but offering quiet solitude as it does not face 5th Ave South. Inside, the space feels bright and airy, with an open-concept layout designed for both effortless entertaining and quiet relaxation. Large windows invite an abundance of natural light to dance across the polished finishes, while the private balcony offers a perfect perch to soak in the tropical breeze and the rhythmic hum of the city below. The kitchen is a chef’s dream, featuring sleek cabinetry, premium appliances, and ample counter space for preparing coastal-inspired meals. The primary suite serves as a serene retreat, complete with a spa-like ensuite bathroom and generous closet space. Every detail in this home has been curated for those who appreciate a lifestyle of convenience and luxury. Whether you're enjoying a sunset dinner at a nearby bistro or spending a slow afternoon by the Gulf, this property offers an unparalleled opportunity to live where everyone else vacations. This is more than just a home; it’s your front-row seat to the very best of Naples.

365 5th AVE S Unit 307, Naples

$27,900,000

6 Beds ⋅ 5.5 Baths ⋅ 226018147 MLS

Experience the pinnacle of beachfront luxury from this extraordinary Naples coastal estate, where timeless Bermuda-inspired architecture meets effortless modern elegance. Perfectly positioned along 108 feet of pristine Gulf frontage, this six-bedroom residence offers an unparalleled opportunity to own a private sanctuary directly on the sugar-white sands of Naples. Evoking the refined charm of Alys Beach, the home’s striking white stucco exterior, parapet walls, and lush manicured landscaping create a serene and sophisticated coastal presence. Ideally located just steps from the new Four Seasons Naples Beach Club and moments from the boutiques and dining of downtown Olde Naples, the property offers a rare combination of privacy, prestige, and walkable convenience. Inside, expansive living spaces are bathed in natural light through walls of French doors that frame breathtaking panoramic views stretching from sand to sea. Thoughtfully designed for both grand entertaining and relaxed coastal living, the residence offers a seamless flow between formal and casual gathering spaces. A dramatic double living room and elegant dining area, complete with a custom beverage station and bar, create an unforgettable setting for hosting family and guests. The chef’s kitchen opens effortlessly to a warm and inviting family room and features a large center island, stone countertops, premium appliances, and a fully appointed butler’s pantry with wine refrigeration. Two luxurious primary suites—one on the main level and another upstairs with a private balcony overlooking the Gulf—provide tranquil retreats designed for ultimate comfort and privacy. A dedicated office on the main floor further enhances the home’s functionality for today’s lifestyle. Every detail throughout the residence reflects exceptional craftsmanship, timeless design, and understated sophistication. From the refined architectural elements to the seamless indoor-outdoor connection, this remarkable property embodies Naples beachfront living at its absolute finest.

23 6TH AVE N, Naples

$4,900,000

4 Beds ⋅ 4.5 Baths ⋅ 226009201 MLS

Ideally positioned on a sun-filled corner lot in the heart of Old Naples, this exceptional 2020-built residence blends timeless coastal elegance with thoughtful modern design. Just one block from Naples Bay and moments to dining and boutiques of 3rd Street South and 5th Avenue South, the location offers the best of accessible Naples living. Designed by MHK Architecture, the home is bright, open, and effortlessly inviting. Expansive windows flood the interiors with natural light, while refined stone flooring and curated finishes create a warm yet sophisticated aesthetic throughout. The thoughtfully designed floor plan features four bedrooms, including two luxurious primary suites, one on the first floor and a private retreat upstairs, offering flexibility for guests and multigenerational living. The main living spaces flow seamlessly to the outdoor area, embracing indoor-outdoor living. At the heart of the home, the chef’s kitchen is stunning and functional, appointed with marble countertops, a statement Lacanche range and oven, Sub-Zero refrigeration and custom cabinetry, a space equally suited for quiet mornings or lively entertaining. Outdoors, the western-exposure pool captures glowing afternoon light and vibrant Naples sunsets, while the corner lot setting enhances privacy and curb appeal. Lush landscaping and charming architectural details complete this coastal retreat. A rare opportunity to own a newer-construction home in Old Naples, just near Naples Bay and a short distance to the beach, fine dining and best of the Naples lifestyle.

901 10th 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

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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.

Olde Naples Homes with Courtyard Exterior Features

Newest Olde Naples Homes with Courtyard Exterior Features

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