Olde Naples Real Estate

Welcome to Olde Naples, a charming and historic subdivision nestled in the heart of Naples, Florida. This coveted neighborhood is located in Collier County, just a stone's throw away from the pristine beaches of the Gulf of Mexico. Olde Naples is renowned for its tree-lined streets, picturesque architecture, and vibrant atmosphere, making it a sought-after destination for both residents and visitors alike.

In Olde Naples, you'll find a unique blend of old-world charm and modern conveniences. Stroll along the iconic 5th Avenue South, where you can explore upscale boutiques, art galleries, and gourmet restaurants. Take a leisurely bike ride to Cambier Park, a lush oasis in the midst of the bustling city, or unwind on the white sandy beaches that are just minutes away.

Real estate in Olde Naples is as diverse as it is desirable, with a mix of historic homes, luxurious estates, and upscale condominiums. Whether you're looking for a quaint cottage or a waterfront mansion, Olde Naples has something to offer for every taste and lifestyle.

Experience the best that Naples has to offer in the charming enclave of Olde Naples. With its prime location, rich history, and vibrant community, this subdivision is the perfect place to call home. Come and discover the magic of Olde Naples – where timeless elegance meets modern sophistication.

Newest Listings in Olde Naples

$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

$4,599,000

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

$6,490,000

5 Beds ⋅ 5 Baths ⋅ 226030692 MLS

Enjoy the southern end of Old Naples in the perfect spot between two of the most prized streets; Gulf Shore Blvd and Gordon Drive. Just a block from the beach and a minute distance from Third Street shopping/dining, this home is an ideal location for beach lovers and metropolitans who value their privacy. Unwind on the spacious, covered outdoor living area, or in the pool and spa at the end of a long day. The spacious master bedroom with dual walk-in closets is located next to the office. With a layout that lends itself to convenient living and spacious suites for guests, this home is perfect for any type of entertaining. Converted to Natural Gas in 2021 and re-roofed in 2024, this home has the convenience and peace of mind actions taken that one looks for in an Old Naples home. A rare opportunity to enjoy one of the most coveted locations in the nation.

155 20th AVE S, Naples

$6,795,000

5 Beds ⋅ 5.5 Baths ⋅ 226029571 MLS

This exemplary home in a walk-to-beach-and-town location lives like brand new and is beautifully maintained. Built by Provident Beach Houses, this elegant home was featured in HGTV's Ultimate House Hunt as a 2023 Finalist for Amazing Kitchens. The gourmet kitchen features a Bertazzoni gas range, a huge center island, hidden pantry space, glass display cabinets and ample storage. The thoughtfully curated details throughout draw inspiration from tropical Dutch West Indies architecture, including wide smoked white oak hardwood flooring and 11 ft ceilings with whitewashed beams. The spacious primary suite opens directly to the pool and lanai and boasts a 15 ft beamed ceiling, motorized blinds and shades, enormous bath with double sinks, separate tub, multiple shower heads and a generous custom closet. The family room with built-ins opens seamlessly to the kitchen and lanai and a private office/5th bedroom wing offers a quiet retreat of its own. Upstairs, three additional en suite bedrooms surround an expansive game/living room with an exposed high-beam hip ceiling and built-in cabinetry complemented by a full second-floor laundry room and two balconies overlooking the pool and lanai. Outside, the tropical landscaping and full western exposure combine to capture those coveted Naples sunsets and a feeling of being on a perpetual vacation. The lanai is a true entertainer’s oasis with a summer kitchen featuring outdoor grill and sink, covered seating with retractable screens, a shell stone paver pool deck with glass railings, gas-heated pool, large party spa with LED accent lighting, sunny seating areas plus an outdoor shower. Additional features include plantation shutters and motorized shades new in 2024, wired for security and exterior cameras, Lutron lighting system, tankless hot water heater, whole house generator plus attached garage designed with room for car lifts.

1140 8th ST S, Naples

$2,695,000

3 Beds ⋅ 2.5 Baths ⋅ 226028107 MLS ⋅ Olde Naples BLDG.

Fantastic opportunity on 5th Avenue! Experience luxury downtown Naples living in this exceptional residence at 780 Fifth. This open and spacious floor plan features beautiful travertine flooring, elegant crown molding, and a stunning recently updated kitchen with quartz countertops and a large island perfect for entertaining. Offering two private suites plus a generous den with closet that easily converts to a third bedroom (with shared bath), the primary ensuite boasts wide-plank hardwood floors and spa-like comfort. Step outside to your spacious private balcony overlooking iconic 5th Avenue South— your front-row seat to the St. Patrick’s Day Parade, art shows, and spectacular nightly sunsets. Cambier Park is located just behind the building for added green space and events. Residents enjoy a rooftop pool with park and city views, under-building parking, and the ultimate walkable lifestyle. Restaurants, boutiques, galleries, and the beach are all right here. Live where every day feels like a vacation in the heart of Olde Naples.

780 5th AVE S Unit 203, 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

$5,950,000

4 Beds ⋅ 5.5 Baths ⋅ 226026258 MLS

Olde Naples corner-lot estate pairs ultra-luxury design with elite walkability. Dramatic 20ft great room features floor-to-ceiling glass & crystal sphere chandelier. Light-washed oak floors flow into a culinary kitchen with professional gas range & artisan blue beaded statement chandelier. Main-floor primary sanctuary offers direct courtyard access, glass sitting lounge & spa bath with freestanding soaking tub. Upstairs, a sunlit mezzanine loft study overlooks the great room, plus 2 en-suite guest suites and a covered veranda. Detached private guest house with separate entry provides an exclusive retreat or studio. Private tropical courtyard rivals elite resorts, showcasing a pool with cobalt-blue tile spa, triple waterfall wall & loggia with summer kitchen & gas fireplace. Unrivaled walkable lifestyle: 6 blocks to pristine white-sand Gulf beaches, 5 blocks to elite dining/boutiques on 3rd St S & 5 blocks to world-class 5th Ave S shopping.

1011 6th ST S, Naples

$4,750,000

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

$6,300,000

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

$2,500,000

226007021 MLS

One or more photo(s) has been virtually staged, AI generated or rendered. This prime lot (0.22 Acres) features a private ALLEY ACCESS, allowing for a discreet rear-entry garage—perfect for ADDITIONAL GARAGE BAYS, a collector’s showcase, golf cart storage, or space for watercraft and toys. This thoughtful feature enhances both privacy and architectural flexibility, ensuring your vision can flourish. This BUILD-READY homesite presents a rare chance to create a custom coastal retreat tailored to your vision. Positioned north of Central Avenue in one of Olde Naples most distinguished and highly sought-after residential settings. Surrounded by elegant estates and lush tropical landscapes, the property offers both prestige and limitless potential in an iconic Olde Naples locale. Just blocks from the vibrant pulse of Fifth Avenue South, this location offers effortless access to the city’s finest dining, designer boutiques, art galleries, and curated cultural experiences. Old Naples’ charm is unparalleled: a harmonious blend of high energy and relaxed coastal elegance. Beyond the downtown vibrancy, this homesite is just moments from Naples’ iconic white-sand beaches, where morning strolls, ocean breezes, and unparalleled sunsets await. Build your dream! Live in the Naples lifestyle. Embrace the extraordinary! A Property video is attached to the listing to enhance your vision. Keep Living The Dream

760 1st AVE N, Naples

$2,775,000

3 Beds ⋅ 3.5 Baths ⋅ 226025430 MLS ⋅ Olde Naples BLDG.

This is your opportunity to live within the heart of Olde Naples and reside within one of Southwest Florida's most sought after newer construction luxury downtown condominiums. 875 Sixth Avenue consists of only eight exclusive condominiums within walking distance to all of the great amenities offered within the charming Downtown Olde Naples. Enjoy delicious hors d'oeuvres and cocktails with your friends and family atop your private rooftop before walking to one of the many fabulous restaurants along the coveted 5th Avenue. Take a swim in your private 60ft rooftop infinity edge pool and unwind in your spacious hot tub overlooking incredible sunsets. Soak up some sun along Naples' coveted white sandy beaches. Immerse yourself in luxury living with features such as imported Legno Bastone hardwood flooring, arctic white quartz countertops, Hansgrohe fixtures, and a neutral contemporary pallet which has been professionally designed with custom finishes and built-ins. Unit 304 offers an air conditioned spacious storage unit in addition to a secondary garage level storage unit and two underground parking spaces. Do not miss your chance to experience this incredibly rare opportunity in person. Schedule your private tour today!

875 6th AVE S Unit 304, 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.