Olde Naples, Naples, FL Real Estate Search

Olde Naples, Naples, FL 5 Bedroom Homes for Sale

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Newest Olde Naples, Naples, FL 5 Bedroom Homes for Sale

$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
$8,350,000
5 Beds ⋅ 5.5 Baths ⋅ 226017504 MLS
Perfectly positioned on a coveted corner of 2nd Street South and 7th Avenue South, this exceptional Olde Naples estate captures the essence of timeless coastal elegance paired with elevated modern design. Enveloped beneath a canopy of majestic oak trees and oriented for prized southern exposure, the residence is bathed in natural light, creating a luminous and inviting ambiance throughout. Masterfully designed by MHK Architecture, this five-bedroom plus den home is a refined interpretation of the classic Florida cottage, thoughtfully reimagined with sophisticated architectural detail and contemporary flair. Interiors are curated with an uncompromising eye—where bespoke finishes, clean lines, and warm textures come together to create a seamless balance of comfort and luxury. Indoor outdoor living is perfectly matched with a private lush landscaped backyard featuring a gas outdoor kitchen, fireplace & heated pool & spa. Just two blocks from the sugar-white sands of the Gulf and moments from the world-class boutiques and dining of Fifth Avenue South, the home offers an unparalleled walkable lifestyle in one of Naples’ most prestigious enclaves. This is a rare opportunity to own a signature property in the heart of Olde Naples—where iconic charm, thoughtful design, and modern sophistication converge in effortless harmony.

685 2nd ST S, 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 and walkable luxury. Just steps from Fifth Avenue South, Gulf beaches, and directly across from Cambier Park. The residence features a spacious open floor plan with vaulted ceilings, Miami-Dade pine floors, and timeless beadboard details. The living, dining, and kitchen areas flow seamlessly, creating an ideal setting for both relaxed coastal living and elegant entertaining with room for large family gatherings. Recent improvements include a new standing seam metal roof and a new main air conditioning system installed in 2025, offering enhanced durability, efficiency, and peace of mind. Outdoor living is highlighted by a heated swimming pool, multiple lounge and grassy lawn areas. This is a rare opportunity to own a classic coastal home in a premier walk-to-everything location in Olde Naples. Excellent rental history.

660 8th AVE S, Naples
$13,995,000
5 Beds ⋅ 6.5 Baths ⋅ 226013404 MLS
Steps from the shimmering Gulf waters, pristine white-sand beaches, and the vibrant charm of 5th Avenue South and 3rd Street South, 264 8th Avenue South offers the ultimate Olde Naples lifestyle—where prime location, refined luxury, and effortless living converge. Designed by Beck Architectural Group, this stunning home sits on a premium southern-exposure lot in the heart of Olde Naples. The thoughtfully designed floor plan prioritizes main-level living, featuring an expansive great room, a chef’s kitchen, a luxurious primary suite, and a versatile private flex bedroom—ideal for guests, a home office, or a wellness space. Seamless indoor-outdoor flow leads to a private backyard retreat designed for year-round enjoyment. The covered outdoor living area is outfitted with a gourmet kitchen featuring a Lynx grill, refrigerated drawers, and a prep sink, along with a living space anchored by a feature wall with a television and gas fireplace. Beyond, the sun-drenched, fenced backyard is maximized with a large saltwater pool with a sun shelf, water features, and an integrated spa, all surrounded by ample deck space for lounging, low-maintenance turf for pets, and an outdoor shower. The designer kitchen by Design West is a true showpiece, appointed with custom cabinetry and top-of-the-line appliances, including a Wolf induction cooktop and oven; Sub-Zero refrigeration with wine storage and auxiliary beverage drawers; a Cove dishwasher; and Cristallo quartzite countertops. The adjacent butler’s pantry enhances functionality with additional prep space, a Wolf six-burner gas range, Wolf microwave, Asko dishwasher, and a generous walk-in pantry—perfectly tucked away for effortless entertaining. The main-level primary suite is a private sanctuary, featuring a vaulted ceiling, tranquil backyard views, and a spa-inspired bath with dual vanities, separate water closets, a soaking tub, a walk-in shower, and an oversized custom closet. Upstairs, three spacious bedrooms each offer en suite baths, complemented by a shared media room with a breakfast bar and private deck—an ideal vantage point for breathtaking western sunsets and seasonal fireworks. Throughout the home, rich hardwood flooring, custom retractable privacy shades, and refined architectural details—including 11-inch baseboards—create a sophisticated and cohesive aesthetic. Additional features include dual laundry rooms; a three-car garage with rear alley access and sufficient height to accommodate lifts in two bays; natural gas; a whole-house generator; water filtration and humidification systems; a private elevator; Lutron lighting; surround sound; and full home automation. The property is also situated on the same power grid as a nearby fire station, offering added peace of mind. This exceptional residence perfectly blends Olde Naples elegance with modern luxury—ideal for those seeking the very best in coastal living, location, and sophisticated design.

264 8th AVE S, Naples
$7,500,000
5 Beds ⋅ 8.5 Baths ⋅ 226005784 MLS
This 2022 custom-built home in Old Naples offers the perfect blend of luxury and resilience in an unbeatable location—just steps from NCH Baker Hospital, 5th Avenue South, and the beach. Transitional cottage-style residence with nearly 5,000 sq. ft. of air-conditioned living space, featuring 5 en-suite bedrooms (including a private guest cabana), a dedicated study, gourmet kitchen, wide-plank wood floors, and a spacious fenced backyard. Enjoy the saltwater pool and spa, covered outdoor kitchen, and fireplace—all elevated by concrete construction, natural gas, and impact glass. A rare opportunity to own an elegant, storm-ready coastal retreat in the heart of Old Naples.

739 5th AVE N, Naples
$12,995,000
5 Beds ⋅ 7.5 Baths ⋅ 226002046 MLS
A landmark, custom built, Old Naples estate just four homes from the Gulf. Elevated and recently renovated, this exceptional residence offers over 7,500 square feet of refined AC-living with timeless architecture and exquisite craftsmanship. Features include a grand two-story foyer, coffered ceilings, rich millwork, library, formal dining, and expansive living spaces filled with natural light. The chef’s kitchen boasts Wolf and Sub-Zero appliances, dual islands, marble prep areas, butler’s pantry, and wine cellar. The luxurious master suite offers a sitting area, dual walk-in closets, spa bath, and private balcony. Outdoor living includes a heated, salt system pool and spa, outdoor kitchen, fireplace, lush landscaping, and shaded entertaining areas. Rare, air-conditioned garage for 10+ vehicles, impact windows and doors, private elevator, and generator. High and dry, moments to beaches, dining, and shopping—this is Old Naples luxury at its finest.

140 3rd AVE S, Naples
$11,495,000
5 Beds ⋅ 6.5 Baths ⋅ 225081393 MLS
Introducing 544 13th Avenue South — a newly completed Coastal Contemporary estate that sets a new standard for modern Old Naples living. The striking white façade, elevated entry, and meticulously curated landscaping create an immediate sense of presence and sophistication. Designed by Falcon Design, crafted by Waterside Builders, and finished by Dianna Horsley Design, this residence offers 6,760 sq. ft. under roof and 5,436 sq. ft. under air, delivering a flawless blend of architectural excellence and refined livability. The thoughtful layout provides two main-level bedrooms, including a serene primary suite with spa-quality finishes, and a second bedroom that functions beautifully as a guest suite or dedicated office. Inside, clean lines, designer lighting, and expansive windows fill the home with natural light. The gourmet kitchen is equipped with custom cabinetry, a large center island, top-tier appliances, and a discreet service kitchen ideal for hosting and catered events. The great room opens seamlessly to the outdoors through full-height sliders, creating effortless indoor–outdoor living. The outdoor environment is truly resort-caliber, featuring a stunning pool with sun shelf, expansive decking, integrated seating areas, and a fully equipped summer kitchen — all framed by lush tropical landscaping for beauty and privacy. Upstairs, a private guest suite with a balcony and kitchenette offers exceptional comfort for visitors. A spacious bonus room provides endless flexibility — perfect for a media lounge, gym, bunkroom, or additional bedroom. The second-floor serving bar opens to a large covered balcony overlooking the pool, creating an elevated entertaining space ideal for sunset gatherings. Additional features include a three-car garage, full smart-home integration, a whole-house generator, custom millwork, and a 10-foot elevated front elevation for enhanced peace of mind. Positioned just steps from Historic 3rd Street South, Fifth Avenue South, and the Gulf of America, this residence delivers the ultimate blend of craftsmanship, convenience, and the signature lifestyle that makes Old Naples so sought-after. A brand-new, move-in-ready masterpiece — now complete and ready to be enjoyed!

544 13th AVE S, Naples
$17,950,000
5 Beds ⋅ 7.5 Baths ⋅ 225073939 MLS
Step into refined coastal living with this exceptional new construction home located just two blocks from the beach in the heart of Olde Naples. Designed by Stofft Cooney Architects, built by Equinox Construction Group, and styled by Freestyle Interior Design, this residence blends timeless elegance with modern functionality. The spacious great room floor plan invites seamless indoor-outdoor living, ideal for both relaxed family life and sophisticated entertaining. A chef’s kitchen equipped with premium appliances and a separate prep kitchen offers versatility for everyday meals or catered gatherings. The home features five bedrooms, five full baths, and three half baths, including two luxurious master suites, one on each level, providing privacy and flexibility for family and guests. Additional spaces include a club room, two laundry rooms, and thoughtfully designed living areas throughout. A three-car garage with alley access preserves the classic charm of the front facade while adding convenience. With white oak wood flooring, high-end finishes, a whole-house generator, and an unbeatable location in one of Naples’ most coveted neighborhoods, this property presents a rare opportunity to enjoy brand-new luxury living just moments from the Gulf of Mexico.

285 Central AVE, Naples
$11,995,000
5 Beds ⋅ 6.5 Baths ⋅ 225068377 MLS
Just minutes from the world class shopping and dining on 3rd Street South & Fifth Avenue South, this brand new, never lived in residence embodies refined living in the heart of the highly sought after Olde Naples neighborhood. Blending natural textures with contemporary elegance, the home offers five bedrooms + study, light-filled interiors, and a seamless connection to the outdoors. Walls of sliders open the flexible outdoor living area & kitchen to the pool, creating a harmonious flow between inside and out. Unwind as the sun sets, a glass in hand, embraced by the privacy of your own retreat. At the heart of the gourmet kitchen, a dramatic Calacatta Lasa quartzite island anchors the space, complemented by custom SOHO cabinetry and Wolf appliances, while a striking counter to ceiling window bathes the room in natural light. Multiple stone and wood selections throughout create a warm yet modern atmosphere, while the open design makes everyday living and special occasions effortless. The main level wet bar with chilled wine storage is detailed with a romantic blue Quartzite setting the scene for evenings of gathering, while the upstairs morning bar invites guests to begin each day with ease and elegance. Additional details of note include a built-in generator, motorized screens, Control 4 automation, three car garage and quality of construction to last a lifetime. This Olde Naples gem is the perfect balance of luxury, comfort, and location—steps from the Gulf and curated for the ultimate Naples lifestyle.

273 10th AVE S, Naples
$10,895,000
5 Beds ⋅ 7.5 Baths ⋅ 224028308 MLS
Newly constructed Olde Naples cottage w 4,998 sf of living, southern exposure, built by award winning Calusa Construction. Interiors by award winning deClare Interiors. Open-floor plan w hardwood floors, Wolf/Subzero gourmet kitchen, 2 Cove dishwashers, refrigerator drawers, & wine trough in oversized island. Glass wine display, Solar Innovations folding doors to outdoor entertaining w covered fireplace & outside firepit. Built in grill, pool bath, sun shelf, & large pool. First-floor primary suite w Euro shower/tub, 3 additional en-suite guest bedrooms, separate guest suite, full bath off study. Electric screens & hurricane shutters, whole house generator. Features include built in benches, extensive custom milled wall & ceiling details, 2 laundry rooms, loft/game room, 3 car garage, elevator, Lutron lighting, landscape lighting, walking distance to beaches and upcoming Four Seasons Resort.

690 7th AVE N, Naples
$12,900,000
5 Beds ⋅ 6.5 Baths ⋅ 224012251 MLS
Recently completed! Experience luxury living at its finest in this new construction home nestled in the heart of sought-after Olde Naples. This Southern exposure two-story residence boasts 5 bedrooms + den (optional 6th Bedroom), 5 (2 Half) bathrooms, and multiple living areas including an upstairs loft complete with its own kitchen. The Butler's pantry complements the chef's kitchen featuring high-end appliances, including a gas cooktop and large island. With an open floor plan and a spa-like master suite, this home is designed for comfort and elegance. The outdoor kitchen, expansive outdoor living area, and resort-style pool with a spa offer an ideal setting for lavish entertaining. Waterside Builders, Falcon Design and DLY Design have come together to construct a showstopping masterpiece. Ideally located in the 100 Block of Olde Naples within walking and biking distance of downtown, 5th Avenue South's, and 3rd Street South's, fine dining, world-class, shopping entertainment, and white sand beaches.

128 1ST 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.