Olde Naples Real Estate

Welcome to Olde Naples, a charming and historic subdivision nestled in the heart of Naples, Florida. Renowned for its picturesque streets, Olde Naples offers a unique blend of coastal elegance and small-town charm, making it a coveted destination for both residents and visitors alike.

As you stroll through the tree-lined avenues, you’ll discover a delightful mix of architectural styles, from classic Florida cottages to luxurious Mediterranean-inspired homes. The vibrant community is characterized by its lush landscaping and meticulously maintained properties, creating an inviting atmosphere that feels like a serene retreat.

Olde Naples is perfectly situated just steps away from the stunning white sandy beaches along the Gulf of Mexico. Residents enjoy leisurely walks on the beach, breathtaking sunsets, and an array of water activities. The nearby Naples Pier is a beloved landmark, offering fishing opportunities and a perfect spot for dolphin watching.

The subdivision is also home to an array of upscale boutiques, art galleries, and gourmet dining options, particularly along the famous Third Street South and Fifth Avenue South. Here, you can indulge in fine dining experiences or explore local shops that showcase the best of Naples’ culture and creativity.

Families will appreciate the proximity to top-rated schools and parks, making Olde Naples an ideal place for raising children. With its rich history, vibrant community spirit, and unparalleled location, Olde Naples truly embodies the essence of coastal living in Southwest Florida. Whether you’re looking for a permanent residence or a seasonal getaway, Olde Naples offers a lifestyle that is both luxurious and relaxed. Come and experience the magic of Olde Naples today!

Newest Listings in Olde 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, 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

$5,990,000

4 Beds ⋅ 3 Baths ⋅ 226025317 MLS

Step into a rare piece of Naples history with this exquisitely renovated coastal cottage, once owned by legendary interior designer Albert Hadley. As co-founder of the iconic Parish-Hadley firm, Hadley designed interiors for luminaries including Jackie Kennedy and Brooke Astor—an artistic legacy that continues to resonate throughout this remarkable property. Blending historic charm with modern luxury, the thoughtfully updated main residence offers three bedrooms and two baths, with inviting spaces designed for both relaxed living and elegant entertaining. The chef’s kitchen features custom cabinetry, marble countertops, and premium finishes, while a newly designed wet bar in the dining room—complete with a Sub-Zero wine refrigerator and double beverage drawers—creates the perfect setting for hosting guests. The first-floor bath has been beautifully reimagined with Kohler fixtures, and the second-floor bath offers the same level of refined sophistication. Designed to embrace Naples’ indoor-outdoor lifestyle, the screened porch serves as an extension of the living space, complete with a SunBrite outdoor television and custom furnishings. Overlooking the sun-drenched pool and patio, the space is framed by lush tropical landscaping and desirable southern exposure. A private guest cottage provides exceptional flexibility for family and visitors, featuring a bespoke kitchenette, built-in queen bed with storage, separate bunk room, and a fully remodeled bath. Recent upgrades include a new roof, updated HVAC system, tankless water heater, outdoor shower, complete dormer replacement, extensive subfloor and tile renovations, and a whole-house water filtration system. Timeless architectural details abound, including custom wool rugs, plantation shutters, crown molding, and French doors. A charming white picket fence, alley access, garage, and covered carport enhance both curb appeal and convenience. Ideally located just three blocks from Naples' pristine beaches and a short stroll from the renowned dining, shopping, and entertainment of Third Street South and Fifth Avenue South, this property offers an unparalleled Old Naples lifestyle. Whether enjoyed as a full-time residence or a luxury retreat accommodating 14+ guests, this is a truly rare opportunity to own a distinctive piece of Naples history.

356 11th AVE S, 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

$22,995,000

6 Beds ⋅ 6.5 Baths ⋅ 226024712 MLS

This Gulf-front masterpiece offers an unparalleled blend of location, luxury, Gulf views, and resort-style living. Completely rebuilt in 2024 by Kukk Architecture and The Lykos Group with the exception of one exterior wall to utilized the grandfathered setbacks and maximize an oversized building envelope. The home has experienced no water intrusion in living areas during recent weather events. The residence combines historic charm with sophisticated elegance. Originally built in 1886, the home underwent an extensive three-year renovation and reconstruction. Now practically new, the residence preserves its heritage, grandfathered footprint, and distinctive character while offering modern luxury throughout. The 6,100-square-foot, fully air-conditioned living space maximizes its premier beachfront setting. The well-designed layout offers five spacious bedrooms, five full and two half baths, a private study, and a flexible sixth bedroom. Sweeping Gulf views provide a stunning backdrop. The gourmet kitchen boasts dual Cristallo quartzite islands, top-tier appliances, custom cabinetry, and a service kitchen. Additional features include a private gated entry, two fireplaces, elevator, whole-house generator, automated screens/shutters, water filtration, and ultra-efficient air conditioning. Perfectly positioned on the Gulf, just moments from the dining and boutique shopping of Third Street South and Fifth Avenue South. A rare opportunity in the heart of Old Naples.

55 13th AVE S, Naples

$1,999,999

2 Beds ⋅ 2.5 Baths ⋅ 226025234 MLS ⋅ Olde Naples BLDG.

Welcome to Residence #208 at The Mark on 8th, a luxury turnkey-furnished condominium ideally located in the heart of Olde Naples, just moments from the renowned 5th Avenue South, world-class dining, boutique shopping, art galleries, and the Gulf beaches. This beautifully appointed 2-bedroom, 2-bath residence offers approximately 1,756 square feet of thoughtfully designed living space with desirable southern exposure and a premier amenity-level location, providing convenient access to the community's exceptional resort-style amenities. The open-concept floor plan is filled with natural light from expansive windows and features designer finishes, premium lighting, a spacious private terrace, and a gourmet kitchen with high-end appliances, custom cabinetry, and an oversized island that is ideal for entertaining or everyday living. Developed by Naples Redevelopment, designed by MHK Architecture, and professionally curated by Marcus Jelley, The Mark on 8th is an exclusive 24-residence luxury community offering sophisticated downtown living in one of Naples' most desirable locations. Residence #208 is one of a limited number of condominium-hotel residences within the community, offering flexible weekly or monthly rental opportunities, subject to association rules and local regulations. The residence has an established rental history, offering an attractive opportunity for buyers seeking investment potential, seasonal enjoyment, or both. Being offered turnkey furnished allows for immediate occupancy or rental use. Residents enjoy an exceptional collection of amenities, including a heated resort-style pool and spa, an expansive sun deck, an outdoor kitchen, a fire pit, a clubhouse, a fitness center, a sauna, and an advanced golf simulator. The amenity-level location enhances convenience while creating a seamless indoor-outdoor lifestyle. The seller will consider flexible purchase terms, including potential seller financing or other mutually acceptable purchase arrangements. Whether you're searching for a luxury vacation residence, an investment property with rental flexibility, or a full-time home in the heart of Olde Naples, Residence #208 at The Mark on 8th offers an exceptional opportunity to enjoy the Naples lifestyle.

201 8th ST S Unit 208, Naples

$2,995,000

226024122 MLS

One or more photo(s) has been virtually staged, AI generated or rendered. An exceptional opportunity to create a custom luxury residence in one of Old Naples' most coveted locations. Perfectly positioned just three blocks from the Gulf (approximately a 3-minute walk) and only four blocks from world-renowned Fifth Avenue South (approximately a 2-minute walk), you'll enjoy effortless access to the very best of Old Naples. A standout feature is the property's location within the highly desirable X500 Flood Zone, a rare distinction in Old Naples that provides added peace of mind. Preliminary site and building plans illustrate the potential for an extraordinary 4,100+ square foot luxury residence. Approved building plans are available for separate purchase, presenting a rare opportunity to bypass the lengthy planning and permitting process and begin construction almost immediately.

61 4th ST S, Naples

$2,295,000

3 Beds ⋅ 2.5 Baths ⋅ 226021276 MLS ⋅ Olde Naples BLDG.

Welcome to 625 5th Avenue South in the heart of vibrant downtown Naples. Enter this elegant penthouse residence into a welcoming entry foyer of this thoughtfully redesigned three bedroom, two and one half bath penthouse residence. Soaring ceilings, gorgeous hardwood floors, solid core interior doors, exquisite millwork, and refined architectural details throughout. Master suite oasis serves as a private sanctuary, complete with a custom-designed walk-in closet and a spa-inspired bath featuring a deep soaking tub, oversized walk-in shower, dual vanities, and separate water closet. A true chef’s eat-in kitchen replete with stainless steel appliances, carrara marble countertops, white shaker cabinetry plus breakfast area. Spacious living area with gorgeous fireplace and wall of glass opening out to lanai seamlessly blending indoor/outdoor living. 2 spacious guest bedrooms, hall bathroom plus spacious laundry room. Large home office/media room with double glass doors is ideal for today’s work from home lifestyle. Offering the exclusivity of only 2 residences within the building and no adjoining walls, the home provides an extraordinary level of privacy. Several outdoor living spaces invite you to enjoy the Naples lifestyle, including a generous screened terrace with desirable southern exposure and captivating views. Recent upgrades include impact-resistant windows and doors, storm protection, additional storage, a secure private elevator with coded access, and an assigned garage space. Residents also enjoy access to a community pool. Surrounded by Naples' finest restaurants, boutique shopping, galleries, and entertainment venues, and within walking distance of the white-sand beaches of the Gulf, this remarkable penthouse embodies the very best of luxury downtown living. Easy access to both Naples and Fort Myers airports. A truly exceptional residence.

625 5TH AVE S Unit 302, Naples

$4,995,000

3 Beds ⋅ 3.5 Baths ⋅ 226022088 MLS

On a desired, tree-lined street in the heart of Old Naples, this exceptional residence offers refined coastal luxury just moments from the pristine Gulf beaches and the acclaimed dining, shopping and entertainment of Fifth Avenue South. Situated within The Gables on Sixth Street, an exclusive enclave of only seven residences designed by Harrell & Associates, the home combines privacy, sophistication and an unrivaled location. A gated rear entrance leads to an air-conditioned three-car garage complete with a vehicle lift and custom built-in storage. Spanning more than 4,300 square feet of beautifully designed living space, the light-filled interior showcases rich hardwood and stone flooring, elegant architectural details and a seamless open-concept floor plan. The redesigned chef’s kitchen serves as the heart of the home, featuring premium appliances, custom cabinetry, an oversized island ideal for entertaining and a climate-controlled wine room with capacity for more than 450 bottles. Designed to embrace the Naples lifestyle, expansive walls of glass connect the great room to a stunning outdoor living area. The covered lanai, highlighted by striking glass floor panels suspended above the pool and spa, creates a dramatic architectural focal point. A fully equipped summer kitchen, gas fireplace and retractable screens provide the perfect setting for year-round entertaining and relaxation. The second floor offers three generously sized en-suite guest bedrooms, while the luxurious primary suite serves as a private retreat complete with a serene balcony and spa-inspired bath featuring exceptional finishes and thoughtful design. Blending timeless elegance, modern comfort and an extraordinary convenient location, this residence represents a rare opportunity to enjoy a luxurious coastal lifestyle and the best of Old Naples living.

32 6th ST S, Naples

$2,250,000

2 Beds ⋅ 2 Baths ⋅ 226018464 MLS ⋅ Olde Naples BLDG.

RARELY AVAILABLE! A spectacular corner penthouse residence in the heart of prestigious 5th Avenue S. This light-filled home features 2 bedrooms, 2 full baths, and 3 private balconies, offering the perfect blend of luxury, privacy, and vibrant downtown living. French doors open to a charming balcony overlooking iconic 5th Avenue, where you’ll enjoy warm beach breezes and front-row access to Naples’ renowned parades, art shows, fine dining, boutique shopping, the famous car show, and endless entertainment — all just steps from your door. The spacious primary suite offers a walk-in closet, dual vanities, a large walk-in shower, and a private balcony retreat with black-out drapes. While the second bedroom features ample closet space, a beautiful desk for your convience, balcony access, and an adjacent full bath. Additional highlights include "two assigned parking spaces (one covered), secure building entry, and private penthouse-floor access. "Pets are welcome! Take morning walks along the beach and enjoy breathtaking Gulf sunsets at night, with the sugar-sand shoreline just a short stroll away. An exceptional residence for entertaining with family and friends while enjoying the best of Naples living. Experience the ultimate in Naples luxury living — because Life begins in Naples, come see for yourself

375 5th AVE S Unit 302, Naples

$6,495,000

5 Beds ⋅ 4.5 Baths ⋅ 226020603 MLS

Ideally situated in the heart of downtown Naples, this completely remastered single-family residence embodies the essence of refined Florida living. Thoughtfully designed with elevated finishes throughout, the home welcomes you through a dramatic two-story foyer highlighted by soaring ceilings, architectural millwork, and a striking staircase that sets the tone for the interiors beyond. The flowing floor plan is both spacious and inviting, centered around a beautifully appointed kitchen featuring an oversized island and seamless connection to the dining and living areas — ideal for both everyday living and effortless entertaining. Pocketing impact glass doors open to the covered lanai with a summer kitchen, extending the living space outdoors to a generous lawn perfectly suited for gatherings, pets, and family enjoyment. The first-floor primary suite offers a private retreat, accompanied by a dedicated office, while guests are comfortably accommodated with their own upstairs living area and three ensuite bedrooms. Just moments from the charm of Olde Naples, residents can spend evenings strolling to renowned dining, shopping, and the nearby beaches, enjoying the convenience of downtown living right outside their door.

950 8th ST S, Naples

$12,000,000

4 Beds ⋅ 5.5 Baths ⋅ 226019430 MLS

One or more photo(s) has been virtually staged, AI generated or rendered. Set just steps from the Gulf and the celebrated boutiques and restaurants of Third Street South and Fifth Avenue South, this extraordinary newly built estate embodies the pinnacle of refined Old Naples living. Crafted in 2017, this gorgeously furnished four-bedroom + den residence offers an exceptional blend of timeless coastal elegance and modern luxury across an impeccably curated floor plan. From the moment you enter, the home captivates with soaring ceilings, wide-plank French oak flooring, bespoke millwork and designer lighting that create an atmosphere of understated sophistication. Walls of glass fill the interior with natural light, while seamless indoor-outdoor transitions invite effortless entertaining and relaxed resort-style living. At the heart of the home, the spectacular chef’s kitchen is a true statement of luxury and design, featuring an oversized island, a commanding 48-inch Wolf gas range, dual Sub-Zero refrigeration, Miele built in wine refrigerator, Miele built-in coffee system, premium fixtures and custom cabinetry tailored for both grand-scale entertaining and everyday comfort. Adjacent living and dining spaces are anchored by a beautiful private tropical retreat where every detail has been thoughtfully considered. The outdoor Oasis features a stunning custom pool and spa with oversized sun shelf, towering private bamboo hedge, and outdoor kitchen, creating an atmosphere reminiscent of an exclusive luxury resort. The first-floor primary suite is a serene sanctuary, offering spa-like amenities, a luxurious bath retreat and a custom walk-in wardrobe. A private detached cabana guest suite on the main level provides exceptional comfort and privacy for visitors. Accessible by both a private spacious elevator and staircase, the second level is designed for elevated entertaining and relaxed living alike. A comfortable loft serves as a central gathering space surrounded by 3 beautifully appointed en-suite guest bedrooms. Additional features include impact-resistant doors and windows, whole-house 20- kilowatt generator and the highest level of craftsmanship and finishes throughout. An exceptionally rare offering in one of Naples’ most prestigious locations, this remarkable estate delivers unparalleled luxury, timeless architecture and the ultimate Olde Naples lifestyle just steps from the beach and world-class dining and shopping. This home offers you the convenience of living a life of walking to the beach every day, dining on Third Street, and enjoying the newly opened Olde Naples Hotel which offers a bar for an evening beverage after you enjoy the beautiful Naples sunsets.

160 Broad AVE S, 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.