5 Bedroom Homes for Sale in 34108, Naples, FL

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Welcome to your dedicated resource for 5 bedroom homes for sale in 34108, Naples, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local 34108, Naples, FL agents, The Fortune Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the 5 bedroom properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All 5 Bedroom Homes for Sale in 34108, Naples, FL

$21,995,000

5 Beds ⋅ 6.5 Baths ⋅ 226035993 MLS

Discover an exceptional estate in the prestigious Gulf Shore Drive corridor of Vanderbilt Beach, one of Naples’ most coveted beachfront addresses. Set on an oversized 0.45-acre corner lot, this remarkable residence offers approximately 7,400 square feet under air, with rare panoramic views of both the Gulf and Vanderbilt Bay. With pristine white sands just across the street and a private boat in the backyard, this is the ultimate coastal lifestyle. Expertly crafted by Forge Construction, with architecture by Irwin Design Co. and interiors by Kira Krumm, the residence highlights refined finishes including natural stone, Legno Bastone french white oak flooring, Indonesian wall coverings, and a gourmet kitchen with Wolf and Sub-Zero appliances. Lutron lighting, Control4 automation, and Sonos audio complement the home’s sophisticated lifestyle amenities. Outdoor living takes center stage with a rooftop deck featuring a summer kitchen and fire pit, while a jet ski lift, natural gas, concrete block construction, and a four-car air-conditioned garage with custom lift add exceptional convenience. Moments from LaPlaya Beach & Golf Resort, this rare estate offers an unparalleled opportunity to experience Naples waterfront living at its finest.

10030 Gulf Shore DR, Naples

$6,995,000

5 Beds ⋅ 6 Baths ⋅ 226037394 MLS

SOME HOMES ARE BEAUTIFUL. OTHERS ARE UNFORGETTABLE. At 380 Trade Winds Ave, waterfront living becomes an art form. Here, contemporary architecture meets the ever-changing beauty of the water, creating a residence where exceptional design and an extraordinary coastal setting exist in perfect harmony. Located in the prestigious Connors waterfront community, with the Gulf just minutes from your private dock, this is a home that doesn't simply offer the Naples lifestyle, it gives it an entirely new expression. Originally constructed in 2018 and subsequently transformed through an extraordinary renovation, this remarkable residence blends the advantages of newer construction with the sophistication of a meticulously reimagined modern estate. Offering 4,350 square feet of air-conditioned living space, 5 bedrooms, 6 full bathrooms, a private elevator, and an impressive eight-car garage, every detail reflects a commitment to exceptional living. The luxurious primary suite and three additional en-suite bedrooms provide beautifully appointed retreats, while the fifth bedroom, currently designed as an elegant office, enjoys access to a separate full bathroom. At the heart of the home, a spectacular designer kitchen with TWO expansive islands creates a stunning centerpiece for culinary experiences and memorable gatherings. Beautiful sliding glass doors frame the waterfront scenery, effortlessly connecting the sophisticated interiors with the outdoors. Rich hardwood flooring, custom closets, dramatic architectural accents, and a striking fireplace feature wall create an atmosphere of refined elegance. On the first level, an exquisite custom dry bar and adjoining wine room offer a distinctive setting for showcasing treasured vintages and entertaining in style. A fully integrated Savant smart home system seamlessly controls lighting, climate, security, music, and entertainment, complemented by premium televisions and integrated speakers throughout the residence and outdoor living areas. The completely transformed pool and spa feature shimmering PebbleTec finishes, custom coping, integrated seating, and enchanting evening illumination. A professionally equipped Lynx outdoor kitchen, complemented by a second upper-level outdoor kitchen, create an exceptional atmosphere for entertaining and relaxation. Private dock access and a boat lift invite spontaneous Gulf adventures, while a whole-house generator, custom flood protection system, and sophisticated landscape lighting provide thoughtful convenience. Offered fully furnished with high-end interior and exterior furnishings, this residence delivers an effortless turnkey experience. Where Naples' celebrated coastline meets the privacy of waterfront living, 380 Trade Winds Ave holds a distinctive place in the luxury landscape. This is a rare convergence of architectural sophistication, waterfront privilege, and uncompromising design, created for those who appreciate the exceptional and settle for nothing less.

380 Trade Winds AVE, Naples

$1,549,000

5 Beds ⋅ 5.5 Baths ⋅ 226037153 MLS

The rarest opportunity in Naples Park! A true multi-asset play positioned 0.8 miles from Vanderbilt Beach, delivering scale, flexibility, and immediate income in one of North Naples’ most active rental corridors. This offering centers on a well-composed triplex spread across an oversized parcel, thoughtfully configured with a 2BR + den, 2BA primary residence, a two-level 2BR, 2.5BA unit, and a separate 1BR, 1BA suite. Each residence benefits from recent interior improvements, updated mechanicals, and a new roof, all tied together by a shared pool environment that elevates short-term rental performance. A two-car garage and generous off-street parking solve one of the area’s most common constraints. The true advantage lies in optionality. The seller is prepared to package this asset with the adjacent duplex at 549 94th Ave N creating a five-door configuration with a stabilized long-term tenant already in place. Operate as a hybrid income model, transition fully to short-term rentals, or establish a primary residence while maintaining consistent cash flow from the remaining units. The layout, lot configuration, and shared access provide operational efficiency without sacrificing tenant privacy. Set within a walkable grid west of US-41, the location consistently outperforms due to its proximity to beach access, Mercato, and the broader North Naples lifestyle infrastructure. Demand remains durable across both seasonal and annual tenancy, supporting strong occupancy and rate resilience. Opportunities with this level of unit diversity, location quality, and expansion potential are seldom available in Naples Park. This is not just a property acquisition; it is a scalable income platform in a supply-constrained coastal submarket.

541 94th AVE N, Naples

$10,750,000

5 Beds ⋅ 6.5 Baths ⋅ 226037215 MLS

Grand architecture, a superior interior remodel and exceptional outdoor entertaining distinguish this five-bedroom plus den offering in the Estates at Bay Colony Golf Club. Featuring approximately 8,355 square feet under air, the residence welcomes guests with a sweeping staircase, soaring ceilings and beautifully appointed gathering spaces. A fireplace anchors the formal living room, where expansive windows frame the pool setting. A separate dining room, spacious kitchen, morning room, family room and wet bar accommodate both intimate evenings and larger celebrations. Dedicated media, game and wine rooms add to the home’s extensive entertaining options. The main-level primary suite occupies its own wing with a separate retreat, multiple walk-in closets and an expansive bath. A study and second bedroom complete the main-level accommodations, while three upstairs bedrooms, a loft and balconies provide privacy for guests. An elevator connects the two levels. Outdoor living unfolds across more than 2,000 square feet of covered lanais surrounding the pool, spa, sun shelf and sun deck. The outdoor kitchen features a wood-fired/gas pizza oven, wood-pellet smoker, Fire Magic gas grill, warming drawer and power burner, complemented by two outdoor-rated Sub-Zero refrigerators. The pool house offers a swim-up bar, gas fireplace, television, sink, two additional outdoor-rated Sub-Zero refrigerators and a cube ice maker. An outdoor-rated U-Line nugget ice maker adds convenience, while hurricane-rated shutters allow the pool house to close securely. Whole-house streaming audio and a recently installed outdoor sound system extend the experience throughout the property. Significant updates include a new roof installed in September 2024, exterior painting in 2024, updated exterior lighting, a redone driveway and new pool controls in 2026. A 125-kW generator, two 1,000-gallon propane tanks, mature tropical landscaping and two separate garages with four-car capacity complete this thoughtfully equipped Naples estate.

9880 Brassie BEND, Naples

$3,475,000

5 Beds ⋅ 4.5 Baths ⋅ 226037228 MLS

Paradise awaits beach lovers and boating enthusiasts in the highly sought after Conners at Vanderbilt Beach. This exceptional Gulf access residence offers coveted southern exposure, a private dock with new boat lift, and immediate access to the open waters of the Gulf. Just steps from the sand, the location delivers the ultimate Naples waterfront lifestyle. Designed with architectural intention and a clean coastal aesthetic, the home showcases smooth white walls, soaring ceilings, dramatic half circle arches, and refined designer finishes throughout. The layout flows effortlessly, creating a serene indoor outdoor experience ideal for both entertaining and everyday living. The main level features a spacious great room, an expansive dining area that connects seamlessly to the gourmet kitchen, and a first floor primary suite offering privacy and comfort. A guest bedroom with French doors opens directly to one of two oversized patios, while a full guest bath completes the level. Outdoor living is equally impressive with a resort style pool and spa, outdoor shower, and convenient powder bath designed for seamless entertaining. Upstairs, a flexible landing area serves as a bonus lounge or media space. Three additional bedrooms and two baths, including one ensuite, provide ample space for family or guests. A generous balcony captures coastal breezes, and additional storage enhances functionality. Conners offers the rare advantage of no HOA fees while placing you in the heart of North Naples. Fine dining, upscale shopping, and daily conveniences are moments away, making this property a true blend of luxury, location, and lifestyle.

494 Seagull AVE, Naples

$4,250,000

5 Beds ⋅ 4.5 Baths ⋅ 226035757 MLS

Pine Ridge Estates is sought after for its proximity to all best Naples has to offer, the beach, 5th Avenue, outstanding schools, fine dining, shopping, entertainment. Many of the homes are in the most desirable FEMA flood zone X as is this classic beauty. The streets are friendly for walking and bicycle riding, lots are expansive, and there are no homeowners associations. This timeless home is constructed with quality; an architectural landmark on 1.22 acres was designed by David Corban Design, and custom built by Lundstrom Development. Featured in Gulfshore Life, this home features two primary bedrooms including one on the main floor. Other well-designed features include all ensuite bedrooms, spacious wraparound front porch, movie room with double wall construction, deep saltwater pool, saltwater spa, expansive covered outdoor deck, outdoor kitchen, cabana bath, mud room, large parking pad for boat and other recreational vehicles, storage everywhere, impact windows, completely fenced yard, electric vehicle charging, and so much more! Set in a private and peaceful oasis accentuated by native plant landscaping to enhance natural beauty while reducing maintenance. Fruit trees provide tropical appeal. The spacious, finished third floor offers endless potential for a playroom, hobby room, exercise room, game room. ALL MECHANICALS ARE NEW WITHIN THE PAST 3 YEARS. Ideal location is close to sugar sand beaches, the sparkling allure of fabulous 5th Avenue, the enduring charm of Venetian Village, and the ubiquitous appeal of Mercato center. All this with a history of remaining safe from storms. You are going to love it here.

65 Mahogany DR, Naples

$33,500,000

5 Beds ⋅ 5.5 Baths ⋅ 226035504 MLS

A stunning new home in The Strand at Bay Colony - one of Naples’ most exclusive beachfront communities. Designed by Stofft Cooney Architects and built by BCB Homes, this 5-bedroom, 5.5-bath custom residence blends contemporary coastal design with timeless craftsmanship. Light-filled open spaces feature wide-plank Legno Bastone floors, a 3-sided fireplace, and incredible natural finishes throughout. The gourmet kitchen includes high end appliances, Blue Roma quartzite counters, a full butler’s pantry, and a 400-bottle wine room. The top-floor primary suite offers sweeping Gulf views, dual closets, a spa bath, morning bar, and fitness studio. Outdoor living is a priority here with a resort-style pool, water feature wall, EVO grill, and reclaimed pecky cypress ceilings. It’s built to the highest standards with hurricane-rated windows & doors, generator, Control4 home automation, and private elevator. Wake up to the sound of the surf and walk straight onto the private sands of Bay Colony, or spend the day at the Beach and Tennis Club enjoying oceanfront dining and poolside relaxation. Behind you is 570 acres of untouched conservation land which offers a rare balance of nature and total privacy along Naples’ most coveted coastline.

7409 Bay Colony DR, Naples

$3,999,999

5 Beds ⋅ 5.5 Baths ⋅ 226030192 MLS

One or more photo(s) has been virtually staged, AI generated or rendered. Set along the water in the Conners area of Vanderbilt Beach, 342 Germain Avenue presents a rare Gulf-access waterfront setting on an approximately 0.37-acre tip lot at the end of a cul-de-sac. With approximately 175 feet of waterfront and western exposure, the property is oriented toward expansive water views and sunsets, while its Gulf access creates a direct connection to the boating lifestyle associated with coastal Naples. The two-story residence features five bedrooms, five full baths and one-half bath, with two bedrooms and two full baths on the first floor, plus a pool bath. Iron entry doors open to high ceilings and dual curved marble staircases that frame views toward the water. Throughout the main living areas, the kitchen, dining room and living spaces are positioned to engage with the waterfront setting, creating a foundation for renovation and personalization. Upstairs, the primary suite includes a private study and two terraces, with one overlooking the water and another oriented toward easterly views. Two additional guest bedrooms are en suite, each offering generous closet space and a waterfront balcony. The outdoor spaces extend the residence's connection to the water. An outdoor kitchen and covered dining area are positioned alongside a saltwater pool and spa, gazebo, waterfront deck, boat lift and personal watercraft lift. The extensive waterfront frontage and tip-lot configuration provide multiple vantage points for enjoying the property's coastal setting and accessing the water. The location places Vanderbilt Beach, The Ritz-Carlton, Naples, and the shops and restaurants of Mercato nearby. For buyers seeking a Gulf-access waterfront home in Naples with substantial water frontage, boating infrastructure, and renovation or redevelopment potential, 342 Germain Avenue offers an established property with an opportunity to create a residence tailored to individual preferences. Buyers interested in renovation or redevelopment should independently verify applicable building, zoning and permitting requirements.

342 Germain AVE, Naples

$1,474,900

5 Beds ⋅ 3 Baths ⋅ 226034131 MLS

One or more photo(s) has been virtually staged, AI generated or rendered. LUXURY NEW CONSTRUCTION IN NAPLES PARK — POOL & SPA — PROFESSIONALLY FURNISHED — UPGRADED LANDSCAPING PACKAGE AVAILABLE — NO RENTAL RESTRICTIONS — MINUTES TO VANDERBILT BEACH! Experience elevated coastal living in this exceptional 5-bedroom, 3-bath new-construction residence, where sophisticated design, resort-style amenities, and the coveted Naples Park lifestyle come together beautifully. Professionally decorated and FURNISHED BY AN INTERIOR DESIGNER, this home is equally suited as a luxurious primary residence, an unforgettable seasonal retreat, or a premier short-term rental investment. With NO HOA and no HOA-imposed rental restrictions, the possibilities are exceptional. Step inside to soaring ceilings, an expansive OPEN-CONCEPT layout, and extensive HIGH-END UPGRADES throughout. Wood-look plank PORCELAIN TILE FLOORING flows throughout the home, while custom FLUTED WOOD SLAT ACCENTS introduce warmth, texture, and designer appeal. The living room is anchored by a sleek ELECTRIC FIREPLACE, creating an inviting focal point for both intimate evenings and effortless entertaining. At the heart of the home, the showstopping kitchen pairs striking design with exceptional functionality. Highlights include abundant cabinetry, premium stainless steel appliances, a decorative vent hood, an INDUCTION COOKTOP, and an oversized dine-at island finished with dramatic WATERFALL QUARTZ COUNTERTOPS. The luxurious primary suite offers a private sanctuary with direct access to the outdoor living area, DUAL WALK-IN CLOSETS featuring CUSTOM BUILT-IN ORGANIZERS, and a spa-inspired bathroom appointed with a GLASS-ENCLOSED WALK-IN SHOWER, freestanding SOAKING TUB, and dual vanities. Four additional bedrooms provide impressive flexibility for family, guests, a home office, or a fitness space. Step outside and discover your own private resort. The FULLY FENCED backyard features a sparkling POOL AND SPA, CUSTOM BUILT-IN SUMMER KITCHEN, outdoor shower, and lush landscaping, creating an exceptional setting for relaxing, entertaining, and enjoying the Southwest Florida lifestyle year-round. An UPGRADED BACKYARD LANDSCAPING package is also available, with the seller willing to complete the improvements before closing or provide a buyer credit. Additional features include IMPACT-RESISTANT WINDOWS AND DOORS, a paved driveway, an attached 2-car garage, and NO FLOOD INSURANCE REQUIRED. Every detail has been thoughtfully selected to deliver comfort, style, and peace of mind. Ideally located just minutes from Vanderbilt Beach, Delnor-Wiggins Pass State Park, The Ritz-Carlton, Mercato, Waterside Shops, and some of Naples’ finest dining and entertainment, this remarkable property places the best of Naples at your fingertips. Modern, polished, and completely turnkey, this is Naples Park living at its finest. Schedule your private showing today!

653 107th AVE N, Naples

$6,995,000

5 Beds ⋅ 3.5 Baths ⋅ 226033404 MLS

Nestled within Pine Ridge Estates, this exceptional Naples residence has been completely reimagined with extraordinary attention to architecture, craftsmanship and design. Thoughtfully expanded and comprehensively renovated, the property offers exceptional indoor-outdoor living and an impressive collection of newly created spaces. Just off the foyer, the living room is defined by graceful curved walls and a custom curved herringbone wood floor inlay that follows the architecture of the room. Expansive sliders create a beautiful connection to the pool and grounds. The redesigned kitchen features quartz countertops, professional-grade appliances, generous entertaining areas and an effortless connection to the surrounding living spaces. A thoughtfully designed new addition expanded the residence with a spacious family room directly off the kitchen and a private VIP suite, both featuring 11-foot tray ceilings. The family room offers herringbone wood flooring and extensive glass overlooking the pool and landscaped grounds. The VIP suite continues the home’s refined design with herringbone flooring and a beautifully appointed private bath. The primary suite is a serene and sophisticated retreat, featuring a spacious bedroom with a dramatic vaulted ceiling, dedicated workout room and convenient access to the pool and spa. The luxurious spa-like bath offers large-format surfaces, dual vanities, a freestanding soaking tub, oversized glass-enclosed shower and beautifully designed custom closet. The property has been completely transformed with all-new landscaping, a custom pool and stone hardscape, and a beautifully appointed outdoor kitchen featuring a 42-inch Alfresco grill, a custom hood, True refrigeration, porcelain slab countertops and backsplash. An extraordinary addition to the property is the completely new eight-car garage with an additional dedicated golf cart garage space, providing exceptional capacity for an automobile collection, recreational equipment and storage. The completely renovated, self-contained two-bedroom guest house offers its own living room, kitchen, custom bar, laundry room and full bath. Dramatically veined porcelain slab countertops and backsplashes, custom cabinetry, illuminated floating shelving and a floor-to-ceiling custom wood feature wall with an integrated barn door elevate the interiors. A front porch and spacious rear screened-in porch provide additional private outdoor living. All of this is set within Pine Ridge Estates, known for its generous properties, privacy and distinctive residential character while remaining convenient to Naples Gulf beaches, premier shopping and dining. A rare opportunity to enjoy a thoughtfully expanded and comprehensively redesigned Naples estate with exceptional guest accommodations, remarkable garage capacity and beautifully conceived indoor-outdoor living.

620 Carica RD, Naples

$6,995,000

5 Beds ⋅ 4.5 Baths ⋅ 226033972 MLS

Set on a private, coveted 1.5-acre lakefront homesite in desirable Pine Ridge Estates, this single-story residence offers uninterrupted lake views and sophisticated contemporary design throughout. The floor plan includes 5 bedrooms plus a den, 4 full, 1 half bathrooms, and approximately 4,525 square feet of air conditioned space, with an expansive 4-car garage and impact-resistant windows and doors throughout. Outside, an infinity edge pool and spa anchor the expansive outdoor living area, creating a resort-style retreat overlooking the beautiful lake. The back of the home faces east, providing stunning sunrise views in the morning and a cool outdoor living space in the afternoon. Located in one of North Naples' most desirable non-gated enclaves with no HOA restrictions, minutes from Vanderbilt Beach, Mercato, and Waterside Shops. A rare opportunity to own a like-new lakefront property in Pine Ridge.

6590 Trail BLVD, Naples

$14,995,000

5 Beds ⋅ 6.5 Baths ⋅ 226030849 MLS

**Villa Luminara** is an extraordinary architectural residence where modern luxury, natural light, and resort-style living come together. Situated on 1.18 private acres in prestigious Pine Ridge Estates, this impressive single-story home offers 10,553 total square feet, including 7,890 square feet of air-conditioned living space. Soaring 22-foot ceilings, expansive walls of glass, and warm organic finishes create bright, inviting interiors with a seamless connection to the outdoors. Designed for exceptional entertaining and everyday enjoyment, the outdoor living area is a true private retreat, highlighted by a spectacular 90-foot saltwater pool featuring cascading water elements, four fire bowls, and a dramatic rain waterfall at the bar. An outdoor firewood grill and pizza oven complete this incredible resort-inspired setting. The custom chef’s kitchen features professional-grade Wolf and Sub-Zero appliances, a Pavoni coffee machine, additional refrigeration, and multiple cooking options including gas, induction, and electric. A separate display kitchen, sophisticated bar, and walk-in wine room further elevate the entertaining experience. The residence offers five spacious bedrooms along with beautifully designed living areas featuring custom finishes, imported lighting, and carefully selected details throughout. Additional amenities include a four-car garage with EV charging and lift capability, impact-resistant windows and doors, a 60KW whole-house generator, two tankless water heaters, and a 1,000-gallon propane tank. Offering privacy without sacrificing convenience, Villa Luminara is ideally located just minutes from Naples’ beautiful beaches, Waterside Shops, Mercato, downtown Naples, fine dining, shopping, and entertainment. A truly distinctive property combining architectural design, luxury, and the ultimate Southwest Florida lifestyle.

6616 Trail BLVD, 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.

5 Bedroom Homes for Sale in 34108, Naples, FL

All 5 Bedroom Homes for Sale in 34108, Naples, FL

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