Olde Naples Homes with Resale Property Status Type

Welcome to Olde Naples, a picturesque gem nestled in the heart of Naples, Florida, within Collier County. This enchanting neighborhood is renowned for its charming streets lined with swaying palm trees, vibrant bougainvillea, and an inviting coastal atmosphere that perfectly captures the essence of Florida living. With its rich history and a blend of old-world charm and modern amenities, Olde Naples offers a unique lifestyle that appeals to both families and retirees alike.

Olde Naples boasts a variety of homes, each with its own character and charm. From stunning beachfront estates to quaint bungalows, the real estate market here is diverse, catering to a range of tastes and preferences. Many homes in this area are available for resale, providing an excellent opportunity for buyers seeking to invest in a community that values both heritage and contemporary living. With properties often featuring lush gardens, spacious patios, and proximity to the beach, Olde Naples is perfect for those who appreciate outdoor living and the beauty of nature.

The neighborhood is also home to a vibrant dining and shopping scene, with a plethora of upscale boutiques, art galleries, and gourmet restaurants just a short stroll away. Residents can enjoy leisurely walks along the iconic Naples Pier, where breathtaking sunsets paint the sky in hues of orange and pink, creating a perfect backdrop for evening strolls.

In Olde Naples, you’re not just buying a home; you’re investing in a lifestyle characterized by relaxation, community, and the unparalleled charm of coastal living. Come and discover the magic of Olde Naples – where every day feels like a vacation!

Newest Olde Naples Homes with Resale Property Status Type

$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 5TH Avenue for 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. Redevelopment and rental use are subject to applicable zoning, permitting, and rental requirements. Schedule your private showing today!

442 Central AVE, 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

$1,225,000

2 Beds ⋅ 2 Baths ⋅ 226035097 MLS ⋅ Cardinal Court BLDG.

One or more photo(s) has been virtually staged, AI generated or rendered. One or more photo(s) has been virtually staged, AI generated or rendered. Beautifully renovated in 2026, this sophisticated end-unit residence offers exceptional privacy, abundant natural light and an enviable location in the heart of Olde Naples. Thoughtfully redesigned with a bright, open-concept floor plan, the home features wide-plank tile flooring and refined finishes throughout. The stunning kitchen takes center stage with an oversized island, sleek custom cabinetry, designer stone countertops and full-height backsplash, complemented by premium Thermador appliances. The spacious living area flows seamlessly into an extended glass-enclosed lanai with impact-rated sliders, creating additional year-round living space surrounded by tranquil tropical views. The generous primary suite features a custom-designed closet and beautifully renovated bath with a walk-in shower and contemporary finishes. A comfortable guest bedroom and updated bath provide an inviting retreat for visitors. Additional features include impact windows and doors, in-unit laundry, private garage, additional storage and extra parking. Set within an intimate six-residence building, this desirable end unit combines privacy and lush garden views with an exceptional Olde Naples location. **The residence has never flooded**, offering an additional point of distinction in this highly desirable downtown setting. Just steps from Cambier Park and a short stroll to the renowned shopping, dining and entertainment of Fifth Avenue South, this beautifully renovated residence offers an effortless downtown Naples lifestyle.

990 8TH ST S Unit 1C, Naples

$5,300,000

3 Beds ⋅ 4 Baths ⋅ 226033993 MLS

One or more photo(s) has been virtually staged, AI generated or rendered. A rare Old Naples opportunity offering 0.35 acres and 96 feet of frontage, just a short walk to the beach and the newly completed Four Seasons Resort. Adding to its appeal, the property fronts the Four Seasons golf course, providing an open outlook and no residence directly across the street. MHK Architecture has prepared a report identifying an 8,427-square-foot buildable area and 5,422-square-foot allowable footprint, presenting an exceptional opportunity to create a substantial custom estate in one of Naples’ most coveted locations. The existing 3,016-square-foot residence offers 3 bedrooms plus a den/office, 4 baths, a private pool and spa, and a well-appointed kitchen. Significant improvements completed in 2023 include a new roof, pool heater, HVAC system, water heater, refrigerator and dishwasher, new carpet throughout, kitchen and guest bathroom countertops, and a new guest bathroom off the den. Whether envisioned as a sophisticated renovation or replaced with a new custom residence, this exceptional homesite offers possibilities rarely found in Old Naples. The Gulf beaches and Four Seasons are a short walk away, while 5th Avenue South and 3rd Street South are approximately five minutes by car, placing Naples’ finest dining, boutique shopping, galleries, and downtown amenities within easy reach. Rare land. Exceptional frontage. An open outlook across the Four Seasons golf course. And one of the most coveted locations in Old Naples.

250 S Golf DR, Naples

Start Your Search

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.