Olde Naples Real Estate

Welcome to Olde Naples, a charming and historic neighborhood nestled in the heart of Naples, Florida. Renowned for its stunning beaches, vibrant culture, and exquisite architecture, Olde Naples offers a unique blend of old-world charm and modern sophistication.

As you stroll through the tree-lined streets, you’ll be captivated by the picturesque pastel-colored buildings and lush tropical landscaping. Olde Naples is home to a delightful array of boutique shops, art galleries, and gourmet restaurants, all within walking distance. The renowned 5th Avenue South and 3rd Street South serve as the bustling heartbeat of the area, offering an eclectic mix of dining options and cultural experiences.

Nature enthusiasts will revel in the proximity to the pristine shores of the Gulf of Mexico, where soft sandy beaches meet the sparkling turquoise waters. The picturesque Naples Pier, a local landmark, is perfect for sunset strolls and fishing adventures. For those who enjoy outdoor activities, the nearby Naples Botanical Garden and Clam Pass Park offer breathtaking scenery and serene walking paths.

Olde Naples is also known for its strong sense of community, with numerous events and festivals throughout the year that foster connections among residents and visitors alike. Whether you’re looking for a cozy beach cottage or a luxurious estate, Olde Naples presents a diverse range of real estate options to suit every lifestyle.

Experience the enchanting allure of Olde Naples, where the charm of the past meets the vibrancy of the present, making it the perfect place to call home. Come discover the magic of this coastal gem!

Newest Listings in Olde Naples

$5,757,000

4 Beds ⋅ 3 Baths ⋅ 226036320 MLS

Welcome to The Palm House Old Naples | New Construction | Private Guest Casita Welcome to The Palm House, a stunning new-construction residence in the heart of Old Naples, where timeless coastal charm meets sophisticated luxury. Thoughtfully designed and crafted with the finest materials, this exceptional four-bedroom, three-bath residence showcases impeccable craftsmanship, elegant finishes, and beautifully curated living spaces designed for both refined everyday living and effortless entertaining. Luxurious marble tile and countertops throughout the kitchen and bathrooms add a timeless elegance, complementing the home's sophisticated coastal aesthetic. A private casita offers an inviting retreat for visiting family and friends, complete with a thoughtfully designed morning bar and evening cocktail area—the perfect setting for leisurely mornings and sunset gatherings. Designed for the ease and elegance of Old Naples living, the property features a welcoming circular driveway ideal for convenient arrivals and effortless golf cart living, along with an enclosed garage discreetly accessed from the alleyway, providing secure and convenient parking for your vehicle. Ideally situated in one of Naples’ most coveted neighborhoods, The Palm House is next door to the newly opened, prestigious Four Seasons Resort Naples Beach Club, placing world-class hospitality, pristine beaches, acclaimed dining, charming boutiques, art galleries, and the vibrant energy of downtown Naples just moments away. Seamless indoor-outdoor living, exceptional materials, and impeccable craftsmanship capture the very best of the quintessential Old Naples lifestyle. Located in an X500 flood zone, this remarkable property presents a rare opportunity to own a newly constructed, beautifully appointed residence with a private guest retreat in one of Naples’ most desirable locations. The Palm House—where timeless coastal elegance meets the extraordinary Old Naples lifestyle.

757 Broad CT S, Naples

$815,000

2 Beds ⋅ 2 Baths ⋅ 226035138 MLS ⋅ Buttonwood At Olde Naples BLDG.

COME EARLY AND QUICK to see this gem of a condo nestled in Olde Naples. Surrounded by multi-million-dollar homes on Second Street South in Downtown Naples, this bright, sunny end unit, 2Bedroom/ 2 Bath (0), 55+ and co-op condo is on the 2nd floor of “Buttonwood by the Beach” and has been totally renovated and boasts top design fixtures and state of the art full-size appliances (Bosch & Sharp), plus glass enclosed modern bathrooms! This unit is a “steal” with most same sized condos in the surrounding neighborhoods of Downtown, Naples Square, Venetian Village or the Moorings regularly priced in the $1.5 to $2.0 million and up and is not far from the luxury estate homes of Port Royal by the Gulf. In a low-density building (with only 6 units), this is a perfect “pied a terre” for the busy executive, newly or semi-retired couple who “want to get away from it all” and live in an exciting but peaceful area! No need to join a Fitness Spa here, the condo is located on a peaceful tree lined street, only two blocks from the white sandy beach or a walk up to our famous Fifth Avenue, noted for some great shopping and fabulous gourmet restaurants! Third Street is where our posh locals and tourists go out shopping, dining, or to their Saturday morning Farmers Market! Also, within walking distance or cycling is Cambier Park, the center of our Sunday concerts, or the Jazz Club at the Norris Center…and the city Tennis Club! The Contemporary Art Center is on Park, and up on 41 North near Waterside Shoppes is “Artis Naples” or the former Philharmonic Hall. For those addicted to pickleball, Naples boasts one of the largest Sports Centers, with National competitions all year long, out along US 41 East. So come see your new home, steps away from everything exciting. Drop off your bags, grab your beach towel and run to the beach to catch the setting sun…a quick change and meet your friends for dinner on 5th…then you’ll know you’re in PARADISE! Full details on this fantastic fully renovated condo are available for pickup when you come by to see the unit, which also has a small outside porch; sturdy carport space with tall ceilings; large secure storage lockers and ample space for residents to put their beach gear and bicycles. All Welcome…and at only $815,000!

536 2nd ST S Unit 536, Naples

$775,000

2 Beds ⋅ 2 Baths ⋅ 226035919 MLS ⋅ Cove Inn BLDG.

Rare opportunity to purchase adjoining units in Naples iconic Cove Inn!! Beautifully updated first floor units (these units sit substantially raised) overlooking expansive views of Naples bay! You have the option for personal use or put it in the rental program managed through the Cove Inn, making it completely hassle free. Unit 133 has never been rented, owner used exclusively for personal use. Pristine condition and furnished beautifully! The Cove Inn lobby area is also freshly remodeled/updated giving it a very light beachy feel. Highly desirable Old Naples location! New impact sliders scheduled for installation within the next couple months.

900 Broad AVE S Unit 133/134, Naples

$6,995,000

5 Beds ⋅ 5.5 Baths ⋅ 226019494 MLS

This exceptional Old Naples custom estate is was recently remodeled by Judith Liegeois Design. Showcasing sleek architectural elements, an open floor plan and enhanced through extensive upgrades, this residence epitomizes refined coastal living. Spanning 3,240 square feet under air and 4,872 total square feet, the residence offers five spacious bedrooms and five-and-a-half bathrooms. Every detail has been thoughtfully curated, from the striking modern staircase and pocketing sliders to the detailed crown moulding, oversized baseboards, and elegant wood coffered and tray ceilings. The gourmet kitchen features stainless steel appliances and custom triple-tier cabinetry with glass inserts. Custom wood and tile flooring, along with seamless indoor-outdoor transitions created by pocket sliding doors enhance the home's ambiance. The upper level includes a stylish wet bar and three ensuite guest bedrooms. The outdoor living area is a private tropical oasis, while the lanai features a resort-style pool and spa, an outdoor kitchen with BBQ, a generous seating area, and lush tropical landscaping. Just moments from Fifth Avenue South’s world-class dining, shopping, and white-sand beaches that make Naples one of Florida's most coveted destinations.

473 1st AVE S, Naples

$8,995,000

4 Beds ⋅ 5 Baths ⋅ 226034117 MLS

Perfectly positioned on one of Old Naples’ most sought after, mahogany-lined avenues, this coastal casual masterpiece delivers over 5,000 square feet of refined, effortless luxury living. Classic, timeless, and exquisitely finished, the light-filled open floor plan showcases a stunning great room designed for elevated entertaining. Built in 2015, this meticulously maintained residence lives better than new, featuring wide-plank wood flooring, plantation shutters, and a gourmet chef’s kitchen appointed with Wolf and Sub-Zero appliances. The indulgent, 1,000+ square foot primary suite offers a serene sitting area, an expansive walk-in closet, a morning kitchen, dual water closets, and a private covered balcony overlooking the manicured grounds. A spacious ground floor VIP suite provides flexibility for a main-level primary, and the home includes provisions for a future elevator. Thoughtfully designed with abundant storage, extensive built-ins, and two laundry rooms, the home blends practicality with sophistication. Lush tropical landscaping, palms, and curated flower and herb gardens create a tranquil backdrop for the sun-drenched pool and spa. Moments to the beach and the best of Old Naples, this exceptional residence embodies luxury living at its finest.

501 2nd AVE N, Naples

$3,250,000

2 Beds ⋅ 2 Baths ⋅ 226034990 MLS

LOCATION LOCATION LOCATION !! This charming shabby chic cottage-style residence on a spacious .22-acre lot is located 4 BLOCKS from the BEACH, 5 blocks to 5th Ave, 2 blocks to the library, 7 blocks to the new Gulfshore Playhouse and presents an exceptional opportunity for INVESTORS and BUILDERS seeking a site for a thoughtfully designed Luxury residence. The investment opportunity for 442 Central Avenue centers on the land and its redevelopment potential. Envision a custom home with spacious interiors, seamless indoor-outdoor living, and architectural details that capture the COASTAL LIFESTYLE located at the heart of the Naples renown Cultural Center and Art District. Whether developing for resale, creating a private retreat or creating seasonal income, this is your opportunity! NAPLES GIS FEMA MAP CONFIRMS this home is in the X500 Zone. NO FLOODING from hurricane Irma, Ian or Milton. Central Ave offers a Royal Palm lined street with ample street parking for overflow guests, short walk to boutiques, restaurants, and entertainment with a hospital conveniently located approximately a quarter mile away. Bring your Architect, Builder, or renovation vision to explore both paths: new construction or an income-producing Coastal Retreat. Schedule your private showing today!

442 Central AVE, Naples

$39,000,000

226032729 MLS

Discover the exceptional opportunity to design and build a custom beachfront residence on this expansive Gulf-front property featuring approximately 190 feet of beach frontage—one of the most significant parcels in the heart of Old Naples. Perfectly positioned along the sugar-sand shores of the Gulf, this oversized lot offers the ideal canvas for designing a world-class estate that embodies the best of Naples’ coastal lifestyle. The exceptional lot depth and width provide ample space for a grand architectural statement—complete with lush tropical landscaping, an impressive pool, and generous outdoor living and entertaining areas to capture the essence of indoor-outdoor living. Residents will relish the tranquil sound of waves, spectacular sunsets, and the gentle Gulf breezes that define this rare seaside setting. Situated on Gulf Shore Boulevard, this address represents the pinnacle of Naples exclusivity—just moments from the renowned Third Street South and Fifth Avenue South districts, offering fine dining, boutique shopping, and vibrant cultural experiences. The property is also located within close proximity to the new Four Seasons Naples Beach Club, further enhancing its prestige and desirability. Whether envisioned as a modern architectural masterpiece or a timeless coastal retreat, this unparalleled site presents an opportunity to craft a true legacy home in one of Naples’ most coveted beachfront locations.

275 Gulf Shore BLVD N, Naples

$2,100,000

3 Beds ⋅ 3 Baths ⋅ 226034859 MLS ⋅ Windward Cay BLDG.

LOCATION, LIFESTYLE & INVESTMENT OPPORTUNITY! This fabulous 3-bedroom, 3-bath condo is located within walking distance to 5th Avenue South, 3rd Street South, and the Naples Pier, placing the best of downtown Naples right outside your door. You simply must see this property in person to truly appreciate its amazing location! Expansive windows fill the home with natural light, creating a bright and welcoming atmosphere throughout. The upper level features two bedrooms, two baths, a functional kitchen, and spacious living and dining areas perfect for entertaining. The first level offers a private bedroom and bath, comfortable sitting area, laundry, and an attached garage. Enjoy the ultimate Naples lifestyle with world-class dining, shopping, entertainment, and the beautiful Gulf beaches just a short stroll away. For investors, the property also offers an excellent opportunity with a renter already in place for the 2027 season. Whether you’re looking for a Naples getaway, full-time residence, or investment property, this exceptional location puts you in the heart of it all. Come see for yourself!

640 2nd ST S Unit 2, Naples

$1,900,000

3 Beds ⋅ 2 Baths ⋅ 226034845 MLS ⋅ Terraces Of Olde Naples BLDG.

One or more photo(s) has been virtually staged, AI generated or rendered. "Live Life Beautifully in Southwest Florida" in this beautifully maintained three-bedroom, two-bath turnkey-furnished condo located in the Terraces of Olde Naples. This one-owner residence has been lovingly cared for and lightly used as a guest home for family and friends. Built in 1997 and thoughtfully remodeled, the condo features a bright, elegant kitchen with quartzite countertops, custom cabinetry with glass inserts for displaying, and Thermador appliances, including an induction cooktop & hood above for ventilation, plus built in counter height microwave. The main living areas showcase Bella Cera Oak hardwood flooring, while two bedrooms are carpeted for comfort. The third bedroom is versatile, offering a pullout sofa for additional guests. Enjoy a southern-exposure balcony overlooking Olde Naples, filling the home with natural light from the east, west, and south. Being on the top floor, the residence is exceptionally light and bright. Additional highlights include a custom-designed laundry room with cabinetry, sink, and quartz countertops; extra storage conveniently located on the first-floor foyer; and one private garage space. The primary suite offers a spa-like bathroom with white marble countertops, a beautiful contemporary shower, and a custom-built walk in closet. Just off main living area is a extra large lanai with view of the pool area & access to primary bedroom bringing once again all the natural light we want from SW FL living. Ideally located just blocks from Fifth Avenue South, 3rd Street Shopping/Restaurants & and six blocks from Naples’ pristine beaches, this exceptional property truly has it all.

611 10th AVE S Unit B2, Naples

$4,995,000

3 Beds ⋅ 3 Baths ⋅ 226032348 MLS

Experience rare coastal charm and modern sophistication at the iconic Captain Parker House, ideally located within walking distance of 5th Ave S, 3rd St S, Cambier Park, and the beach. Meticulously restored throughout, the residence showcases old-growth heart pine flooring, shiplap detailing, whimsical designer tile, a freestanding soaking tub, and a bespoke fireplace surfaced in hand-picked oyster shells. The gourmet kitchen is appointed with a French Lacanche gas range, Sub-Zero refrigerator, and built-in wine cooler. Structural and mechanical updates include impact-resistant glass, a standing seam metal roof, Hardie board siding, and a whole-house backup generator. Outside, lush grounds host a grotto pool nestled amid a mature canopy of a 50-foot Royal Poinciana, coconut palms, banana trees, coffee plants, and flowering gardenias.

680 8th AVE S, Naples

$16,990,000

6 Beds ⋅ 7.5 Baths ⋅ 226034183 MLS

Quietly situated at the southernmost end of Gulf Shore Boulevard South, directly across from beach access, this exceptional Olde Naples estate is a true crown jewel, spanning more than one-half acre. Designed by John Cooney of Stofft Cooney Architects and meticulously refurbished throughout, the residence reflects uncompromising craftsmanship and timeless sophistication and can be acquired turnkey furnished for immediate occupancy. From the moment of arrival, the home makes a lasting impression. Flickering gas lanterns, a gracious front porch, and classic symmetrical architecture accented by exquisite millwork create an inviting sense of elegance. Inside, refined finishes abound, including mahogany front doors, rift-sawn white oak flooring, and a striking vaulted ceiling detail upon entry. The living room’s balanced symmetry and detailed millwork flow seamlessly into the gourmet kitchen and dining area, anchored by a 60" Wolf dual-fuel range featuring six burners, an infrared charbroiler, and an infrared griddle. Additional highlights include a Sub-Zero side-by-side refrigerator and freezer, integrated refrigerator drawer systems, and two Miele dishwashers—perfectly suited for both everyday living and entertaining. Thoughtfully curated spaces throughout the home include a bespoke media room with soundproofed walls and a Savant sound system, a handsome study with custom built-in display cabinetry overlooking the pool, a fully reimagined bar and library, and a dedicated fitness studio complete with a steam shower—each space designed for both function and refined living. The estate is comprised of five well-appointed bedrooms, four of which feature en-suite baths, offering refined accommodations for both residents and guests alike. The Master Suite and Bath offer a true private retreat, enveloping you in comfort from head to toe. A tranquil sitting area overlooks the spa and pool, providing a serene backdrop for rest and reflection. Crown moldings and elegant casings throughout enhance the sense of refined craftsmanship, creating a space that feels like a peaceful escape—while remaining unmistakably at home. Following a complete renovation inside and out, the outdoor living spaces are equally compelling. An expansive, oversized porch is designed for rest and relaxation, offering an exceptional poolside setting framed by a preserved Wild Oak tree—an enchanting natural centerpiece that enhances the estate’s sense of serenity and timeless charm. Additional elevated improvements include two side-mounted car lifts, whole-house generator, dual dehumidification systems, a steam shower within the fitness studio underscoring the home’s exceptional level of care, resilience, and thoughtful investment.

1963 Gulf Shore BLVD S, Naples

$10,395,000

5 Beds ⋅ 6.5 Baths ⋅ 226032954 MLS

An extraordinary expression of luxury living in Olde Naples steps from the brand new Four Seasons Resort. This exceptional estate offers an enviable lifestyle just a short stroll from the beach and moments from the celebrated dining, shopping and entertainment of downtown. Sophisticated yet effortlessly livable, the residence blends refined interiors with a spectacular private outdoor retreat. Beyond the interiors, a lush tropical oasis unfolds around a stunning resort-style pool and spa accented by dramatic water features. An impressive cabana-style bar and fully equipped outdoor kitchen anchor expansive covered living and dining areas, creating an exceptional setting for intimate evenings or grand-scale entertaining. A private guest cabana completes the resort experience, offering visitors their own secluded retreat. Inside, beautiful wood flooring, gracious proportions and sophisticated finishes establish an atmosphere of understated elegance. The main-level primary suite is a serene sanctuary, while the beautifully appointed chef’s kitchen combines high-end finishes and exceptional functionality for both everyday living and entertaining. Upstairs, additional bedroom suites are complemented by a generous loft providing a private secondary living space ideal for family and guests. Rarely does a residence so seamlessly combine the privacy and indulgence of a luxury resort with the quintessential Olde Naples lifestyle. With the Gulf beaches within walking distance and the boutiques, galleries and acclaimed restaurants of Fifth Avenue South and Third Street South just moments away, this exceptional estate offers an extraordinary opportunity to experience Naples living at its finest.

241 7TH AVE N, 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.