Olde Naples Homes with Courtyard Exterior

Olde Naples Homes with Courtyard Exterior

Welcome to Olde Naples, a charming and prestigious development located in the heart of Naples, Florida. Known for its luxurious homes and vibrant community, Olde Naples offers the perfect blend of sophistication and relaxation.

Situated in Collier County, Olde Naples is a highly sought-after neighborhood that captures the essence of coastal living. With its proximity to the pristine beaches of the Gulf of Mexico and the vibrant downtown area of Naples, residents can enjoy the best of both worlds.

One of the unique features of the homes in Olde Naples is the Courtyard Exterior design. True to its name, these homes are elegantly designed to feature a private courtyard that serves as a tranquil oasis in the midst of the bustling city. Whether you're looking for a peaceful retreat or a space to entertain guests, the Courtyard Exterior homes in Olde Naples offer the perfect blend of indoor and outdoor living.

With its picturesque streets, lush landscaping, and proximity to world-class amenities, Olde Naples is more than just a place to live – it's a lifestyle. Experience the beauty and elegance of Olde Naples and discover why it's one of the most desirable communities in Southwest Florida.

Newest Olde Naples Homes with Courtyard Exterior

$6,250,000
4 Beds ⋅ 4 Baths ⋅ 226031870 MLS
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 Avenue S, Naples
$5,195,000
3 Beds ⋅ 5 Baths ⋅ 226031441 MLS
In the heart of Olde Naples, this 2020-built courtyard residence blends timeless coastal architecture with refined, resort-style living just moments from 3rd Street South, 5th Avenue South and Naples’ pristine beaches. Shell-stone travertine floors introduce light-filled living and dining spaces designed for effortless entertaining. The chef’s kitchen is appointed with Sub-Zero refrigeration, Lacanche gas cooking, custom cabinetry, and a thoughtfully designed wet bar. A family room opens seamlessly to the private courtyard, creating true indoor-outdoor living. Upstairs, the serene primary suite offers volume ceilings, tailored millwork, and a spa-inspired bath, joined by two en-suite guest suites and a flexible den/office. A private elevator services both levels. The walled courtyard becomes a secluded retreat with heated plunge pool and spa, outdoor kitchen with built-in grill, surround sound, and lush vertical greenery for privacy. Impact-rated windows and doors, smart- home automation, natural gas, metal roof, and a generous two-car garage with storage complete this thoughtfully engineered residence. Beautifully scaled and impeccably maintained, 909 10th Avenue South offers the rare combination of walkability, architectural integrity, and lock-and-leave ease in Olde Naples.

909 10th Avenue S, Naples
$4,599,000
3 Beds ⋅ 4 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 Avenue S, Naples
$4,499,000
5 Beds ⋅ 6 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 Avenue S, Naples
$6,300,000
4 Beds ⋅ 6 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 Avenue S, Naples
$1,870,000
2 Beds ⋅ 2 Baths ⋅ 226027036 MLS
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 Avenue S Unit 307, Naples
$27,900,000
6 Beds ⋅ 6 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
$3,295,000
5 Beds ⋅ 4 Baths ⋅ 226014758 MLS
Ideally located in the heart of Olde Naples, this beautifully renovated five-bedroom, four-bath Key West–style residence offers an exceptional blend of coastal charm, privacy, and walkable luxury. Set well back from the road amid lush tropical landscaping, the home has the secluded feel of a secret garden, yet is just steps from Fifth Avenue South and the Gulf beaches and directly across from Cambier Park. The spacious open floor plan features vaulted ceilings, Miami-Dade pine floors, and timeless beadboard details, creating an inviting setting for entertaining and family gatherings. Rich in Olde Naples history, the home underwent an extensive restoration and expansion that earned it the national grand prize in Better Homes & Gardens’ 1992 Home Improvement Contest. Recent improvements include a new metal roof and main air-conditioning system, both installed in 2025. A heated pool, multiple lounge areas, and grassy lawn enhance the home’s relaxed indoor-outdoor lifestyle. A rare opportunity to own a distinctive Olde Naples home offering character, history, privacy, an exceptional location, and an excellent rental record.

660 8th Avenue S, Naples
$4,900,000
4 Beds ⋅ 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 Avenue S, Naples
$6,900,000
3 Beds ⋅ 4 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 Drive, Naples
$29,500,000
6 Beds ⋅ 6 Baths ⋅ 226001239 MLS
An extraordinary Old Naples beachfront estate, this rare offering encompasses approximately .67 acres with an impressive 169 feet of pristine Gulf frontage, delivering an unparalleled combination of privacy, scale, and a prime location just blocks from the world-class boutiques, galleries, and dining of Fifth Avenue South and Third Street South. Designed by acclaimed architect Richard Morris, the art deco–inspired residence was masterfully conceived to frame sweeping Gulf views and sunsets, showcase fine art and create a seamless indoor–outdoor living experience that feels grand and intimate. A dramatic arrival unfolds into a soaring 22-foot foyer, where a sweeping staircase and private elevator lead to an elevated art gallery, immediately establishing the home’s architectural presence and refined elegance. The light-filled great room serves as the heart of the residence, flowing effortlessly into the dining area, expansive lanai and a sophisticated lounge highlighted by custom millwork and a wet bar, ideal for entertaining against a backdrop of endless blue horizons. A sculptural spiral staircase ascends to a private observation deck, offering breathtaking panoramic views of the Gulf and unforgettable sunsets. The generous kitchen suite is designed for effortless hosting, featuring an open-concept layout with indoor and outdoor dining counters, a walk-in pantry and high-end stainless-steel appliances. The primary suite is a secluded beachfront retreat with direct access to a Gulf-front balcony, pool and lanai, complemented by a spa-inspired bath with a glass-enclosed walk-in shower and mesmerizing water views. Just a short distance away, a private bedroom or den offers flexibility as a refined home office or serene sanctuary. The east wing of the home hosts four spacious en-suite bedrooms and a dedicated laundry, while the northeast bedroom, bathed in exceptional natural light with abundant storage, lends itself beautifully as an artist’s studio or creative space. Outdoors, an elevated screened courtyard and lushly landscaped gardens create a tranquil oasis for year-round enjoyment, while the expansive covered lanai, complete with a kitchenette and dining area, invites relaxed coastal entertaining. Built with exterior block construction, a first-floor elevation exceeding 19 feet above NGVD and electric storm shutters, the home offers exceptional peace of mind along with enduring quality. Professional landscaping, architectural lighting, and iconic outdoor sculptures complete this remarkable setting. Beyond its immediate beauty, the property also presents an extraordinary future opportunity, with the potential to create a 10,000–15,000 square-foot custom beachfront estate, making this a once-in-a-generation offering that blends luxury, lifestyle and limitless possibility in one of Naples desired beachfront locations.

30 3rd Avenue S, Naples
$10,999,000
4 Beds ⋅ 6 Baths ⋅ 225077098 MLS
This extraordinary custom-designed home is the epitome of luxurious living in downtown Naples. A true collaboration of the distinguished C&E Builders and the celebrated Ruta Menaghlazi of Theory Design—this one-of-a-kind property effortlessly blends impeccable craftsmanship with modern elegance. Located just moments from the pristine sugar-sand beaches and within walking distance to the world-class shopping, dining, and entertainment of 5th Avenue South, 3rd Street, and the highly anticipated Naples Beach Club, it offers an unparalleled lifestyle. Upon entering, you are greeted by an breathtaking floating staircase that serves as a striking focal point of the home. The open-concept floorplan is bathed in natural light, with soaring ceilings adorned with wood beams that create a beautiful contrast against the sleek ebony accents throughout the home. This is no ordinary new construction—it's a masterpiece that balances warmth and sophistication in a way that feels uniquely refined and inviting. The heart of the home is its exquisite chef’s kitchen, where luxurious marble countertops and backsplashes provide a breathtaking backdrop to an expansive center island—perfect for entertaining and casual dining alike. This culinary haven features top-of-the-line Miele and Sub-Zero appliances, a dream for any gourmet chef, while the tastefully concealed butler’s pantry enhances the kitchen’s functionality, providing ample space for prep and storage. The primary suite is a retreat, curated for relaxation and comfort. The spa-like master bathroom features stunning marble tile, a luxurious soaking tub, and an oversized shower with multiple showerheads for a true resort experience. Step outside to the tranquil pool area, surrounded by lush landscaping. Designed for entertaining, this home boasts an exceptional indoor-outdoor flow. The outdoor space is adorned with a custom-built fireplace, a summer kitchen, and stunning marble accents, creating the perfect environment for alfresco dining or lounging by the pool. Upstairs, an additional living area serves as a versatile loft complete with a full wet bar—ideal for guests or family members to enjoy their own private space separate from the main living area downstairs. The upper level also features the VIP guest suite, equipped with a full kitchenette, making it the perfect in-law or au pair suite for extended stays. With over 5,000 square feet of thoughtfully designed living space, this home represents the pinnacle of indoor-outdoor living in Naples. The blend of European white oak wood flooring, elegant architectural details, and a sophisticated color palette sets the tone for a residence that is both timeless and contemporary. This custom-built masterpiece is more than just a home—it’s a testament to the finest in Naples living, where every detail has been carefully designed for those with discerning taste.

349 2nd Avenue N, Naples
Start Your Search