Upper Captiva, FL Real Estate For Sale

Lee County | Updated
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Castaway Key, 621 Rum Rd, Upper Captiva, Florida 33924, image 1
$1,299,000$291K
  • 3 Beds
  • 31/2 Baths
  • 2,481 SqFt
  • $524/SqFt
Mid-Tier
House for sale in Castaway Key
621 Rum Rd, Upper Captiva, FL 33924
Upper captiva canal home. Room for two boats. Needs some updating. Beautiful private views across the state park to pine island from this gorgeous 3 bedroom plus a den & 3.5 bathroom home. It has everything you would want from an island home including protected docking for your boats on a navigable canal which leads out to the gulf of mexico and the intracoastal waterway, an elevator to bring groceries and supplies up to the kitchen, all windows are hurricane impact windows, cedar ship-lap exterior siding, wood burning fireplace, an upper mezzanine area above the living room which could be a studio or office, plenty of room for guests, a beautiful kitchen with big windows showing the view to the state park, wide decks wrap around the house on both floors, a large screened-in pool with a shower and bathroom, new electric system inside and out, new roof, newly painted decks, newly painted exterior. Also, recent maintenance check on the elevator. The beach is just down the sandy path to a parking area with access to the widest beach on the island. This island home could be an exceptional income producing property. Please make an appointment to see this wonderful home soon.
Safety Harbor Club, 370 Townhouse Lane 61, Upper Captiva, Florida 33924, image 1
$510,000$90K
  • 3 Beds
  • 2 Baths
  • 989 SqFt
  • $516/SqFt
Mid-Tier
Townhouse for sale in Safety Harbor Club
370 Townhouse Lane 61, Upper Captiva, FL 33924
Steps from the water! You can hear the bay waters gently sloshing against the shoreline from the front deck. Enjoy beautiful bay views from the front screened-in deck and watch the boats come and go from safety harbor. Relax to the sounds of the cheerful sea birds that soar over safety harbor and watch the dolphins swim in the bay. This meticulously maintained townhouse has gorgeous views of safety harbor. New roof in 2023. The master suite has an updated bathroom with walk-in shower, and there is a peaceful screened-in sitting area right off the master bedroom. Two adorable bedrooms are upstairs, with sweeping bay views from one of the upstairs bedrooms. The lower area has brand new flooring, a laundry area, and full golf cart garage to park your golf cart (included). The community dockage is just steps away from the front door, with additional slips available at the community wharf where you will find a fish cleaning station and plenty of docks to fish from. Also steps away from the front door is a lovely bay beach where you can launch your kayak (included) or go fishing. Membership with safety harbor club includes a community heated pool, tennis and pickle ball, private beach access, a restaurant on the water, clubhouse, and miles of pristine, uncrowded, white sugar-sand gulf beaches. North captiva is an island with no roads to it, so ride the bi-hourly island girl ferry from pineland marina to north captiva and get around the island on golf carts. This unique feature of the island makes it particularly peaceful and attractive.
Punta Robalo, 211 Kingfisher Dr, Upper Captiva, Florida 33924, image 1
$3,924,999$526K
  • 4 Beds
  • 5 Baths
  • 3,938 SqFt
  • $997/SqFt
High-End
House for sale in Punta Robalo
211 Kingfisher Dr, Upper Captiva, FL 33924
Not everyone can get here… and that’s exactly the point. Indiana jones adventure meets luxury island living | rare fly-in / boat-in captiva estate. Set along the waters of pine island sound with views to the gulf of america, this extraordinary upper captiva property offers one of the most unique lifestyles in southwest florida. Located on approximately 1.16 acres, this private island retreat is accessible by boat or private aircraft via salty approach airstrip (fl90), upper captiva’s private 1, 800-foot grass runway. The property also includes a hangar below the home, making it ideal for aviation enthusiasts. Fl90 is best suited for experienced pilots flying light aircraft designed for short-field and turf operations, including planes in the style of cessna 150, 152, 172, 182, 206, piper cub, super cub, aviat husky, maule, kitfox, and similar stol-capable aircraft. For seaplane owners, welcome home. The residence features 5 bedrooms, 5 bathrooms, and over 3, 900 square feet designed to capture panoramic water views and sunsets. A private elevator services all four levels. Inside, the home offers spacious living and entertaining areas with marble, tile, and wood flooring throughout. The chef’s kitchen includes premium appliances, wine and beverage refrigeration, ice maker, and an open layout ideal for hosting. Outdoor living is exceptional, with expansive terraces and gathering spaces overlooking the water. A new trex waterfront deck leads to a private composite dock with boat lift, ideal for a 40-foot viking for serious fishing adventures, plus a fast boat such as a nortech or midnight express for island-hopping and cruising. The dock may also accommodate a seaplane. Additional features include whole-house generator, hurricane impact windows and doors with shutters, outdoor kitchen, poolside cabana, exercise room, multiple entertaining spaces, and well water, septic, and propane gas service. A rare combination of privacy, adventure, and luxury waterfront living in one of southwest florida’s most exclusive island communities. Created for those who crave privacy, adventure, and a true sense of escape, this estate offers a lifestyle few properties can match. Spend your mornings heading out by viking for serious fishing, your afternoons cruising by fast boat to nearby islands, and your evenings enjoying panoramic sunsets over pine island sound. With a hangar below the home, private dockage, expansive terraces, and resort-style outdoor living, every detail supports an effortless fly-in, boat-in island lifestyle. This is more than a residence. It is a gateway to one of the most extraordinary waterfront experiences in southwest florida. With exceptional access to boca grande’s renowned deep-water fishing right from your back door, this remarkable estate is designed for the buyer who expects the extraordinary. Complete with a private sauna and every luxury appointment. The 29'5" x 36'7" hangar-style garage offers substantial space for aircraft.
North Captiva Sands, 120 Swallow Dr, Upper Captiva, Florida 33924, image 1
$1,125,000$150K
  • 5 Beds
  • 31/2 Baths
  • 1,682 SqFt
  • $669/SqFt
High-End
House for sale in North Captiva Sands
120 Swallow Dr, Upper Captiva, FL 33924
Exceptional opportunity to own a beautifully renovated 5-bedroom, 3.5-bath island retreat just a short walk from the pristine gulf beaches of north captiva island. Offering 1, 682 square feet of living space, this coastal home combines modern updates with the relaxed island lifestyle that makes north captiva one of southwest florida's most unique destinations. Accessible only by boat or private aircraft, north captiva offers miles of uncrowded beaches, world-class fishing, breathtaking sunsets, and a peaceful atmosphere free from cars and traffic. Thoughtfully designed to accommodate large families and guests, the home offers plenty of space to spread out across multiple living areas and outdoor gathering spaces. The main level features a king primary suite with private ensuite bath, a queen guest bedroom, and a custom bunk room with four twin beds. The lower-level in-law suite provides exceptional flexibility with a king bedroom, a bedroom with two twin beds, a second living area, kitchenette with sink and microwave, and a full bath, making it ideal for extended family, guests, or vacation rental accommodations. Every level of the home features decks and outdoor living areas, including two screened porches with overhead fans for enjoying island breezes year-round. The crow's nest rooftop deck offers stunning 360-degree views of the island, gulf waters, and unforgettable sunrises and sunsets. Extensive recent improvements include a new roof, new siding, updated electrical, new water system, new hot water tank, fresh interior and exterior paint, new decking, a newly constructed crow's nest, rescreened porches, updated landscaping and driveway improvements, new poly outdoor furnishings, luxury vinyl plank flooring, tile flooring, and granite countertops in the bathrooms. Currently operating as a successful vacation rental, this property offers outstanding income-producing potential while also serving as the perfect private island getaway. Two golf carts are included for convenient transportation throughout the island. Whether you're seeking a personal retreat, full-time residence, or established investment property, this exceptional north captiva home is ready to be enjoyed.
Captiva Palma, 4511 Bartlett Pkwy, Upper Captiva, Florida 33924, image 1
$1,075,000$124K
  • 3 Beds
  • 2 Baths
  • 1,500 SqFt
  • $717/SqFt
High-End
House for sale in Captiva Palma
4511 Bartlett Pkwy, Upper Captiva, FL 33924
A must see! Priced to move! North captiva island fabulous young island pool home! Beautiful coastal turnkey furnished three bedroom, two full baths, single family stilt, 2021 year built on a private and oversized half acre - corner lot! Fantastic on island location! Close to the beach and seconds to the island club at north captiva its’ marina, mangos restaurant and bar, mangos convenience store, and the boats and fun island store. Bright, open, great room floor plan. Split bedroom floor plan. Lovely kitchen with large center island with breakfast bar. Great sized bedrooms and upgraded full baths. Wonderful front screened balcony and large back open balcony overlooking the inground pool and grounds. Other features and upgrades include: ideal newer construction, impact resistant windows and doors, hardie board siding, new whirlpool appliances, granite countertops, dual sinks in both baths, upgraded tile bath walls, convenient laundry room with washer and dryer, luxury tile plank flooring throughout, vaulted ceilings, metal roof, two covered carport area(s), large, heated, salt water pool, outdoor summer kitchen, entry gate plus a gorgeous, fenced yard - a lush tropical oasis with mature assorted palms and including five coconut palms. Turnkey furnished and ready for rentals should you wish for rental income too with professional licensed mgmt. Special note: a boat slip with covered boat lift is also offered for sale in addition to this home sale at $235k. It accommodates up to 26’boat and 10klbs. Please inquire with agents! Paradise awaits! Now is the time to make “hidden garden” your island dream home and/or investment opportunity! Schedule your showing today! Newest home at this price point!
Safety Harbor Club, 370 Townhouse Ln #66, Upper Captiva, Florida 33924, image 1
$490,000$39K
  • 3 Beds
  • 2 Baths
  • 953 SqFt
  • $514/SqFt
Mid-Tier
Townhouse for sale in Safety Harbor Club
370 Townhouse Ln #66, Upper Captiva, FL 33924
Priced to sell! Positioned directly on the harbor in safety harbor club, this waterfront townhome offers one of the most convenient dockside locations on north captiva island. With the boat docks less than 50 feet from your door, this home is ideal for those who want immediate access to boating and waterfront living. The layout is designed to capture excellent harbor views while providing comfortable island living. Light-filled interior spaces flow naturally to the outdoor covered screen porch, where you can watch boats come and go and enjoy the serene waterfront setting. As part of safety harbor club, owners enjoy a full suite of amenities including a community pool, tennis & pickleball courts, clubhouse, on-site dining, & gulf beach access. The nearby ferry landing makes travel simple while maintaining the peaceful, car-free charm of north captiva. Whether used as a personal retreat or investment property, this harborfront townhome offers an exceptional combination of location, lifestyle, and boating convenience on one of florida’s most unique barrier islands. There is a tenant currently in place until july 31, 2026.
North Captiva Dunes, 4481 Butterfly Shell Dr, Upper Captiva, Florida 33924, image 1
$999,500$80K
  • 2 Beds
  • 11/2 Baths
  • 1,232 SqFt
  • $811/SqFt
High-End
House for sale in North Captiva Dunes
4481 Butterfly Shell Dr, Upper Captiva, FL 33924
A must see! Wow opportunity. North captiva, private heated saltwater pool, gulf-side location, turnkey furnished, rental history and 150+ five-star guest reviews. 64k in rentals in 2026 alone to date! Welcome to “the perfect shell, ” a fabulous turnkey island beach home offering an exceptional south gulf-side location, private heated saltwater pool, easy beach access and impressive vacation-rental history with 150+ five-star reviews! Situated on a desirable high-and-dry lot in captiva dunes, this charming stilt home is just a short walk or golf-cart ride to the wide sugar-sand shoreline of sunset beach, known for spectacular sunsets, shelling, fishing, swimming and sandbars. Additional prime surrounding lots may be available for purchase by the buyer, offering a unique opportunity for added privacy or expansion. Strap: 05-45-21-08-00000.0350 & 05-45-21-08-00000.0090 inside, a bright, open great-room floor plan captures beautiful tropical views and opens to an expansive screened front balcony with sliders, ceiling fan and recessed lighting. The home offers 2 bedrooms and 1.5 baths and is sold turnkey furnished with lovely furnishings, fixtures and window coverings. The kitchen features a long breakfast bar, corian countertops, recessed lighting, appliances and gas range. The primary bedroom includes a large closet. The main bath offers a large tiled shower and corian-topped vanity. The half bath includes a sink, extensive built-in cabinetry, countertops and full-size stacked washer/dryer, with potential for a second full bath if desired. Outside, the large heated saltwater pool features built-in seating shelves, aluminum fencing and expansive brick-paver decking with wonderful sun exposure. A generous side yard provides additional outdoor space and room to expand. The spacious under-house area offers even more possibilities for entertaining—add an outdoor shower, changing area, bath, bar or outdoor kitchen. Enjoy the best of island living with exceptional outdoor space, tropical surroundings and easy access to one of north captiva’s most beautiful beaches. Great property layout with a large side yard, pool area and room to expand—an increasingly special combination on the island. Simply a must-see! Recent improvements and features include a 2024 white standing-seam metal roof, 2023 hvac, 2025 exterior paint, 2023 whole-house reverse-osmosis system, hurricane-impact windows and doors, hardie-board siding, tile throughout and attached ground-level garage. For buyers interested in vacation-rental income, the perfect shell has an established rental history with many repeat annual guests. The property is professionally managed, with continued management available. Best of all, this is a private pool home with no hoa fees or club membership to assume! Whether you're looking for your own north captiva getaway, an established vacation-rental property, or a combo of personal enjoyment & income potential. Exceptional location
Jose's Hideaway, 4620 Oro Pesos Ln, Upper Captiva, Florida 33924, image 1
$3,250,000$250K
  • 4 Beds
  • 41/2 Baths
  • 2,115 SqFt
  • $1,537/SqFt
Mid-Tier
House for sale in Jose's Hideaway
4620 Oro Pesos Ln, Upper Captiva, FL 33924
Gulf-front luxury living on the pristine beaches of north captiva island, offering a rare two-lot homesite with sweeping panoramic views of the gulf of america, captiva pass, and cayo costa island, where unforgettable sunsets unfold nightly. Thoughtfully designed for comfort, resilience, and effortless island living, this exceptional residence features a whole-house reverse osmosis system, private well and septic (not shared), a 1, 000-gallon propane tank powering a full-house kohler generator, propane gas range, and tankless water heater to ensure uninterrupted comfort. The gourmet kitchen is equipped with high-end appliances and expansive west-facing sliders that frame breathtaking water views and open seamlessly to indoor-outdoor entertaining. Outdoor living is elevated with expansive deck space, a shaded area beneath the home, outdoor refrigerator and icemaker, heated saltwater pool, six-person spa, full outdoor entertainment system, and outdoor shower—ideal for hosting or relaxing after a day on the water. The spacious climate-controlled garage includes air conditioning, room for golf carts, bicycles, beach gear, a workbench, and a convenient service elevator with a 300-lb capacity for groceries and luggage. The fully fenced yard offers manicured green grass and a sprinkler system, a rarity on the island. Zoned for weekly rentals, this property presents outstanding investment potential while remaining a serene private retreat. Ownership includes a one-year membership to the island club at north captiva. Access is by private boat or ferry; overnight dockage is not included unless purchased separately, with two memberships available at safety harbor offering dockage and amenities—contact safety harbor for details. The private airstrip is available to members only through the salty approach association. A truly rare opportunity to own a gulf-front estate with scale, privacy, and flexibility—this two-lot offering delivers endless possibilities and will not last. Schedule your private showing today!
Beach Villas Of Upper Captiva, 640 Gulf Ln #4, Upper Captiva, Florida 33924, image 1
$1,349,000$101K
  • 2 Beds
  • 2 Baths
  • 1,124 SqFt
  • $1,200/SqFt
Ultra Luxury
Villa for sale in Beach Villas Of Upper Captiva
640 Gulf Ln #4, Upper Captiva, FL 33924
Motivated seller bring your offers! Prime island offering! Exquisite prime island beach front remodeled townhome “ocean waves”! Boat slip with covered lift for sale additional with this home purchase. 26ft maximum boat size and 10, 000 lb covered boat lift please inquire! Fantastic vacation rental or gulf front home! This high end, newly remodeled, gulf front and beach front townhouse makes up one half of this duplex property. This turnkey villa offers two main owner suites and two full baths. It has undergone gorgeous and extensive renovations and offers breath taking views of the gulf of mexico from its deck, porches, and balcony! Aside from the elegant brand open new kitchen with huge breakfast bar, upscale baths, appliances, flooring, electrical, fixtures, fans, finish carpentry, paint, electric fireplace, and turnkey furnishings, this amazing property has a brand new metal roof, hardie board siding, impact windows and doors, new whole house reverse osmosis water system, railings, stairs, and more. This turnkey furnished villa has fantastic rental history and potential gearing up for a busy florida winter season. Located directly on the wide butterfly beach on the barrier island of north captiva with private beach access. The property's shoreline provides an abundance of the finest and most beautiful shells and its' gulf waters offers world class fishing! The islands state nature preserve is also only steps away. The islands sea and wildlife are magnificent to enjoy! An island club at north captiva memberships is available please inquire to enjoy their pools, spa, kayaks, fat tire bikes, basketball, activities and island services etc. Professional licensed property mgmt with upcoming rentals is already in place should you choose to enjoy your townhomes and/or value its’ rental income! This is a must see property located directly on the beach. Tropical and lush, this duplex sits in a spectacular location on island. *the entire duplex is also currently for available for sale. Ask agents about unit 3! Rare is this unparalleled opportunity to own an entire gulf front and beach front luxury duplex in a spectacular location on butterfly beach!
Castaway Key, 4541 Conch Shell Dr, Upper Captiva, Florida 33924, image 1
$1,395,000$100K
  • 3 Beds
  • 31/2 Baths
  • 1,646 SqFt
  • $848/SqFt
Mid-Tier
House for sale in Castaway Key
4541 Conch Shell Dr, Upper Captiva, FL 33924
An island masterpiece! This elegant, custom-designed island estate blends traditional island-style charm with contemporary sophistication. The home's exquisite detailing and bold roof lines create a unique and timeless design. Sited on an oversized lot close to gulf beaches on a quiet sandy lane. Hardie board siding, pella impact windows, and electric storm shutters provide peace of mind. The private heated pool and screened outdoor entertainment area offer relaxation and island fun. Perfectly designed for high-volume vacation rentals. A grand two-story foyer welcomes you inside with an elegant winding wood staircase. Two spacious primary suites on the first level offer en suite baths with custom tile walk-in showers. The third guest bedroom enjoys its adjacent upgraded bath with a tub/shower. On the next level, the luxurious custom kitchen sparkles with granite countertops & stainless steel appliances. Deep dark wood cabinetry throughout the kitchen space offers elegantly curved corner cupboards for a sleek and functional appeal. Built-in yacht-style dining that seats 12+ in a three-side banquette uses the space ideally for entertaining. The living area meanders from the cozy tv/media area to covered screen porches and three levels of outdoor sundecks. Upstairs, the vaulted natural wood ceiling loft is a stunning focal point and versatile fourth sleeping space, offering gorgeous gulf views through expansive sliding glass doors. Step up to the top lookout deck, where panoramic vistas of the gulf and the island's natural beauty unfold. A rare blend of refined elegance and island serenity, this exceptional home is a magical seaside spot to enjoy your new island beach lifestyle.
Beach Villas Of Upper Captiva, 640 Gulf Ln #3, Upper Captiva, Florida 33924, image 1
$1,299,000$91K
  • 2 Beds
  • 2 Baths
  • 1,124 SqFt
  • $1,156/SqFt
Ultra Luxury
Townhouse for sale in Beach Villas Of Upper Captiva
640 Gulf Ln #3, Upper Captiva, FL 33924
Motivated seller bring your offers! Prime island offering! Desired vacation rental! Boat slip with covered lift for sale additional with this home purchase. 26ft maximum boat size and 10, 000 lb covered boat lift please inquire! Rare is this unapparelled opportunity to own a gulf front and beach front luxury townhome in a spectacular location on butterfly beach! Attached, high end, brand new remodeled, gulf front and beach front! This turnkey villa called "beach dayz" offers two main owner suites and two full baths. This beach villa has undergone gorgeous and extensive renovations and both offer breath taking views of the gulf of mexico from its decks, porches, and balconies! Aside from the elegant brand new open kitchen & upscale baths, appliances, flooring, electrical, fixtures, fans, finish carpentry, paint, electric fireplaces, and turnkey furnishings, this amazing property has a brand new metal roof, hardie board siding, impact windows and doors, new whole house reverse osmosis water system, railings, stairs, and more. This turnkey furnished villa has fantastic rental history and potential! Located directly on the wide butterfly beach on the barrier island of north captiva with private beach access. The property's shoreline provides an abundance of the finest and most beautiful shells and its' gulf waters offers world class fishing! The islands state nature preserve is also only steps away. The islands sea and wildlife are magnificent to behold. An island club at north captiva memberships is available please inquire to enjoy their pools, spa, kayaks, fat tire bikes, basketball, activities and island services etc. Professional licensed property mgmt with upcoming rentals is already in place should you choose to enjoy your townhomes and/or value its’ rental income! This is a must see property located directly on the beach. Tropical and lush, this duplex sits in a spectacular location on island. *the entire duplex is also currently for available for sale please see 640 gulf ln #4* rare is this unparalleled opportunity to own an entire gulf front and beach front luxury duplex in a spectacular location on butterfly beach! Hurry to schedule your showings today!
Jose's Hideaway, 4500 Seair Ln, Upper Captiva, Florida 33924, image 1
$1,499,000$96K
  • 3 Beds
  • 3 Baths
  • 1,808 SqFt
  • $829/SqFt
Mid-Tier
House for sale in Jose's Hideaway
4500 Seair Ln, Upper Captiva, FL 33924
One of the newest homes recently built on north captiva! Just completed in 2022, this home still feels pristine and like brand new! Built to the latest wind codes and with upgraded interior fixtures, decor, and finish. This 3 bedroom and 3 bath home is located directly on north captiva's private airstrip, offering excellent access for pilots as well as scenic views of the gulf and bay. The reverse floorplan of this home even offers views from the lower bedroom level as you gaze across the green space of the airstrip to the beaches at either end. The master suite offers a full en suite bath with a walk-in shower, private commode room, double sinks, and a large dressing room/closet. A large laundry space is conveniently located between the bedrooms. Two more exquisitely decorated guest bedrooms share a hallway bath with a deep soaking tub/shower combo. The upper level will impress with its large open-concept kitchen, dining, and living space open to the large covered and screened outdoor porch. The kitchen's central island will become the heart of your home, with dining spots on each side of the island. This kitchen offers a full pantry, quartz countertops, stainless steel appliances, large amounts of storage space, seating, and more. You have views of the bay right from a cozy coffee corner table, while the sparkling waters of the gulf are just outside your sliding glass doors. Enjoy the sunsets from your top-level lookout tower just off the living area. The private elevator rises from your ground-level entrance space and storage garage to the first and second levels of the home for your convenience and comfort. If you have been looking for a newer, move-in home on north captiva, this is the one! Don't miss it!
Safety Harbor Club, 370 Townhouse Ln #60, Upper Captiva, Florida 33924, image 1
$470,000$29K
  • 3 Beds
  • 2 Baths
  • 954 SqFt
  • $493/SqFt
Mid-Tier
Townhouse for sale in Safety Harbor Club
370 Townhouse Ln #60, Upper Captiva, FL 33924
End unit with harbor views & dock access! Experience the tropical island waterfront lifestyle! This value-priced townhome offers shared dockage for your boat, and an unbeatable location just steps from the dockage, ferry landing, and club restaurant… because sometimes the outside is doing all the heavy lifting. Let’s be clear: the interior is authentically, unapologetically vintage. We’re talking original finishes, original fixtures, and décor. The kitchen and baths? Classic. The vibe? Beach retro. The opportunity? Endless. But here’s the thing—this townhome is livable, functional, and ready for its next chapter. Whether you’re dreaming of a full renovation, a creative reimagining, or simply embracing the throwback charm (we won’t judge), this is your chance to start with a light-and-airy plan in an even better location. And what a location it is—end unit, harbor views, steps to dockage and kayak beach... And just a short distance to everything safety harbor club has to offer. Enjoy access to a heated pool, tennis and pickleball courts, clubhouse dining, and private gulf beach access where the sunsets are always in style (no renovation required). Bring your vision. Bring your contractor. Or bring your love for 1985. Either way, this is your chance to secure a waterfront foothold in an end unit at a price that leaves room for transformation. Don’t miss this unique before-and-after opportunity.
Safety Harbor Club, 484 Gulf Bend Dr, Upper Captiva, Florida 33924, image 1
$1,750,000$100K
  • 3 Beds
  • 3 Baths
  • 2,435 SqFt
  • $719/SqFt
Mid-Tier
House for sale in Safety Harbor Club
484 Gulf Bend Dr, Upper Captiva, FL 33924
Great opportunity! This is your chance for a large prime gulf front beach home! This amazing home is right on the beach with private beach access just steps out the door. Simply spectacular oceans views from the entire beach side of this property! This large beach home is located in the fantastic safety harbor club offering the availability of shared boat dockage for it’s members – a commodity that boaters will love! Safety harbor also features a community pool, clubhouse, tennis/pickleball courts etc. Located on an oversized lot on the wide sugar sand of butterfly beach - this 2400 sq ft+ beach house with a great room floor plan offers three bedrooms, three full baths, over 2400 plus square interior footage, plus a loft and interior storage room. With its' bright huge main living area with soaring ceilings, beautiful recess lighting, coffered ceilings, large kitchen and breath-taking oceans views you can envision the full potential of this beach front beauty right upon your entry! Two brs have ensuite full baths. There is also a fantastic screened balcony with access off of the primary br and living room, a large open balcony off of the loft offering superb gulf views and unforgettable sunsets and a nice side deck! Great under house area offers plenty of enclosed storage and covered carport areas. All new recent upgrades include: new roof and gutters. Three new ac units. New water heater. New hurricane shutters with hand cranks and motors. New hurricane door(s) loft, both sets of sliders in the living room, sliders in the primary bedroom and refrigerator. Windows are all hurricane impact rated per seller. New hunter fans in the main living area - sitting area, dining and kitchen plus new fans in the loft, guest and primary br. New lighting primary br. The home’s interior is freshly painted and there is new exterior paint. Two baths are remodeled with all new showers, vanities, faucets, mirrors etc. New kitchen faucet, fan, microwave. New dehumidifiers with custom drains to exterior. Etc. Schedule your showing today to see all that this beach home has to offer! It is a must see!
North Captiva Dunes, 4580 OYSTER SHELL DR & 370th Townhouse Ln #60, Upper Captiva, Florida 33924, image 1
$865,000$25K
  • 3 Beds
  • 2 Baths
  • 954 SqFt
  • $907/SqFt
High-End
Townhouse for sale in North Captiva Dunes
4580 OYSTER SHELL DR & 370th Townhouse Ln #60, Upper Captiva, FL 33924
Dock your boat and enjoy water views from an end-unit townhome, while you build your dream home on an incredible lot with direct views toward the beach and gulf! Introducing a unique island ownership combination: townhome #60 at 370 townhouse ln (parcel id: 05-45-21-03-00000.0600) in safety harbor club, paired with a separate buildable homesite at 4580 oyster shell dr, offered together as an exceptional package. The townhome offers immediate enjoyment with beautiful harbor views, shared community dockage steps away, and full access to all safety harbor club amenities, including a heated pool, tennis courts, pickleball, clubhouse, dining, convenient ferry landing, and private gulf beach access. Perfectly positioned within safety harbor club, the townhome provides an ideal home base for boating, beach days, and island living, with rental or personal-use flexibility. Included in this package is 4580 oyster shell dr, a valuable homesite with incredible views!  You will be stunned by the amazing view corridor looking down onto the sugar-sand beach and sparkling gulf waters beyond.  Imagine watching the sun set every night right from your living room. This lot plus townhome combination is a must-see!
Castaway Key, 660 Gulf Ln, Upper Captiva, Florida 33924, image 1
$3,895,000$100K
  • 4 Beds
  • 41/2 Baths
  • 3,340 SqFt
  • $1,166/SqFt
Mid-Tier
House for sale in Castaway Key
660 Gulf Ln, Upper Captiva, FL 33924
Beauty & the beach is one of the most extraordinary gulf-front estate homes ever offered for sale on north captiva island! This custom-crafted contemporary residence sits on the central portion of the island's widest stretch of beach, providing greater long-term shoreline security and uninterrupted panoramic gulf views. A proven luxury vacation rental leader, this home generated over $360k in gross rentals in 2021.  The property booked over $250k in gross rentals in 2025, even with downtime for repairs and upgrades.  This is a rare opportunity to acquire both a premier vacation retreat and a top-tier rental asset. Designed with a striking stucco exterior, impact-resistant glass throughout, and a private interior elevator serving all three levels, the home delivers refined coastal architecture paired with modern convenience. The ground-level area provides a bonus room & bunk area, plus an extensive outdoor entertainment space with a pool, patio, outdoor kitchen & poolside bar, all connected by a private walkway to the island's most pristine sugar-sand beach. Inside, every space is meticulously planned & designed for elevated entertaining & relaxed luxury. Highlights include a gourmet chef's kitchen, a dramatic dining room crowned by soaring barrel-vaulted ceilings, and a formal living area wrapped in panoramic glass. A built-in fireplace with television above the hearth anchors the living space with warmth and elegance.  The two primary living levels were designed to capture the spectacular gulf and sunset views.   The 4 elegant bedroom suites provide marvelous spaces for you and your guests to experience five-star resort-style luxury sleeping accommodations. The top-level primary suite boasts panoramic beach views, an en suite bath with a walk-in shower, a dual-sink vanity, and a lockable owners' closet.  Imagine relaxing in the extra-deep soaking tub while you stare at the shimmering waters lapping the shoreline. The second primary suite, located just off the entertainment den/media room, offers excellent beach views & a luxury en suite bath with a walk-in shower. Two more north-facing guest suites create "family-suite-style" guest zones with a gulf-facing king bed suite & en suite bath, plus an adjacent bedroom & bath.  Opportunities to acquire a gulf-front estate of this caliber, location, and proven income performance are exceedingly rare on north captiva island. Beauty & the beach represents the very best of luxury island living!
Safety Harbor Club, 406 Gulf Bend Dr, Upper Captiva, Florida 33924, image 1
$1,970,000$30K
  • 3 Beds
  • 3 Baths
  • 2,454 SqFt
  • $803/SqFt
Mid-Tier
House for sale in Safety Harbor Club
406 Gulf Bend Dr, Upper Captiva, FL 33924
Rare opportunity to purchase luxurious gulf front estate on north captiva island a rare opportunity has arisen to purchase a luxurious gulf front estate located within the prestigious community of safety harbor club on north captiva island. This stunning coastal property boasts beach frontage with breathtaking sunsets and panoramic views of the gulf. Recently renovated and remodeled with the highest quality craftsmanship and attention to detail, this estate is truly one-of-a-kind. The interior of the property features a striking custom staircase, quartz countertops, and custom solid wood cabinetry in the kitchen. Beautiful oak and porcelain floors run throughout the home, creating a sense of elegance and luxury. The estate includes two guest bedrooms. One ensuite. The highlight of the property is the exquisite master bedroom, located on the second floor with private decks offering stunning views of the gulf. The master bedroom also features a fireplace and a large bathroom with a jet tub and separate shower. The spacious kitchen is equipped with an island cooktop, downdraft ventilation, subzero refrigerator/freezer, microwave with convection, wall oven, and dishwasher. The property offers gorgeous views of the beach from the master bedroom, kitchen, dining area, and great room. This custom home is truly a gem and must be seen to be fully appreciated. Schedule an appointment today to view this beautiful estate and make it your own.
North Captiva Dunes, 4440 Oyster Shell Dr, Upper Captiva, Florida 33924, image 1
$150,000
  • 0.2 Acres
  • $750,000/Acre
High-End
Land for sale in North Captiva Dunes
4440 Oyster Shell Dr, Upper Captiva, FL 33924
Amazing opportunity to build your dream vacation paradise. Arrive by sea or by air to your private home in upper captiva island. Just steps away to multiple beach access areas and an abundance of preserve land to explore. This piece of paradise will afford a perfect setting for nature enthusiasts.
North Captiva Dunes, 4490 Oyster Shell Dr, Upper Captiva, Florida 33924, image 1
$1,450,000
  • 4 Beds
  • 31/2 Baths
  • 2,262 SqFt
  • $641/SqFt
High-End
House for sale in North Captiva Dunes
4490 Oyster Shell Dr, Upper Captiva, FL 33924
High-performing, income-producing vacation rental on one of north captiva island's premier streets. Privately nestled among mature tropical landscaping, this beautifully maintained 4-bedroom, 3.5-bath island retreat offers over 2, 300 sq ft of thoughtfully designed living space and a proven history of strong rental performance. Guests are drawn to the resort-style outdoor living, featuring an exceptionally large private pool, hot tub and outdoor shower, multiple entertaining areas, and a spectacular southwest-facing third-floor lanai that fully opens to the living room, creating a seamless indoor/outdoor living experience. Two en-suite bedrooms, a bunk room with a third bath, and a fourth queen suite provide ideal accommodations for owners and guests alike. Recent upgrades include hardie plank siding, two hvac systems, trex decking, a brazilian hardwood pool deck, a cargo/luggage lift, and a paver driveway. A rare opportunity to own a turnkey island property that combines exceptional rental income, lush tropical privacy, premium outdoor amenities, and one of north captiva's most desirable locations.
North Captiva Dunes, 4510 Oyster Shell Dr, Upper Captiva, Florida 33924, image 1
$1,300,000
  • 3 Beds
  • 21/2 Baths
  • 1,656 SqFt
  • $785/SqFt
High-End
House for sale in North Captiva Dunes
4510 Oyster Shell Dr, Upper Captiva, FL 33924
Elevated living, gulf views & rooftop sunsets imagine pulling up in your golf cart, the breeze already shifting as you arrive at a home set high and dry in one of north captiva's most sought-after neighborhoods. 4510 oyster shell dr is a 3-bedroom, 2.5-bath retreat with an additional 4th sleeping room, designed to make the most of island life. The reverse floorplan captures gulf views and coastal light from the moment you step into the main living level. Upstairs, the open-concept living, dining, and kitchen area feels bright, easy, and inviting—perfect for gathering after a day at the beach or hosting friends for a laid-back island evening. Large windows and elevated positioning bring the outdoors in, while the surrounding landscape and water views remind you exactly why you're here. And just down the sandy lane lies one of the island's true treasures—a premier beach access point leading to north captiva's widest stretch of powder-soft, sugar-white sand. This is the kind of beach people travel across the world to find—expansive, uncrowded, and endlessly walkable—where mornings begin with quiet shoreline strolls and evenings end with unforgettable gulf sunsets. Then there's the rooftop lookout—one of those features that quietly becomes your favorite place. Morning coffee surrounded by water views as the island wakes up… sunset cocktails as the sky turns gold… and quiet nights under a blanket of stars with the preserve stretching out below. Recent upgrades, including a new metal roof, hardie board siding, and aluminum railings, add both durability and a clean coastal finish. Positioned along one of the island's highest ridgelines—with elevated construction and storm shutters—the home offers an added sense of confidence and comfort. This isn't just a vacation home—it's a place where beach days feel effortless, sunsets feel personal, and every visit makes it harder to leave. Come see it for yourself—and picture where your mornings, beach walks, and next chapter could begin.
North Captiva Sands, 201 White Pelican Dr, Upper Captiva, Florida 33924, image 1
$799,000
  • 2 Beds
  • 3 Baths
  • 1,472 SqFt
  • $543/SqFt
High-End
House for sale in North Captiva Sands
201 White Pelican Dr, Upper Captiva, FL 33924
Escape to the laid-back charm of old florida with this elevated island retreat on beautiful north captiva, located less than 300 feet from the beach—just steps from the sand and gulf waters. This unique property also includes an adjoining lot, providing exceptional flexibility for a future pool, expansion of the existing home, or construction of an additional residence. The main home features one bedroom, two bathrooms, and a versatile den that can easily serve as a second bedroom, while the ground-level apartment offers an additional bedroom and bathroom—perfect for guests, extended family, or rental use. Multiple outdoor decks provide plenty of space to relax and enjoy the island breeze and partial gulf views, while several storage buildings offer convenient space for golf carts, beach gear, and island essentials. Accessible only by boat or small plane, north captiva offers a truly unique car-free lifestyle where golf carts, bicycles, and walking are the preferred ways to get around. Surrounded by nature, pristine beaches, boating, fishing, and strong vacation-rental appeal, this property offers an incredible opportunity to own a versatile piece of island paradise. Schedule your private showing and experience the north captiva lifestyle for yourself!
North Captiva Sands, 210 Nighthawk Dr, Upper Captiva, Florida 33924, image 1
$779,000
  • 2 Beds
  • 1 Baths
  • 974 SqFt
  • $800/SqFt
High-End
House for sale in North Captiva Sands
210 Nighthawk Dr, Upper Captiva, FL 33924
Almost beachfront!  Don't miss this cute beach cottage just steps to the beach with incredible views from the front porch.  Sit back, relax, and enjoy the gulf  & sunset, surrounded by the sounds of the surf, with the expansive grass airfield as a wonderful buffer from other homes. A perfect spot for your dream retreat this close to the beach. Start your mornings with a walk along the shoreline, spend the afternoon swimming and shelling, and return home to enjoy it all from the shady front porch. Upstairs features panoramic gulf & airstrip views, plus two bedrooms & one bath, with a cozy living space. On the ground level, another bonus sleeping room and bath are great for extra guests. For aviation enthusiasts, the setting is especially unique: the property directly borders north captiva's private grass airstrip, creating the possibility of turning the journey to your island home into part of the adventure. North captiva is a boat-access-only barrier island known for miles of beautiful beaches, protected preserve lands, abundant wildlife, and its relaxed golf-cart lifestyle. Whether you're looking for a personal beach escape, vacation property, or a special north captiva home with an aviation connection, this property offers a combination of beach proximity, gulf views, privacy, and location that's difficult to duplicate at this price point.
Castaway Key, 4561 Smugglers Dr, Upper Captiva, Florida 33924, image 1
$624,900
  • 2 Beds
  • 11/2 Baths
  • 891 SqFt
  • $701/SqFt
Mid-Tier
House for sale in Castaway Key
4561 Smugglers Dr, Upper Captiva, FL 33924
Adorable island cottage on beautiful north captiva island with classic beach style. This bungalow offers three sleeping rooms, making great use of the space. The living room and kitchen area are full of charm with tongue-and-groove wood walls, an authentic coastal retreat style. The two levels of decking are great for watching sunsets and gathering with the family. The home is located on a valuable oversized lot, just a short stroll or golf cart ride to the nearest beach access. Plenty of room to add on or install a large pool and outdoor entertainment area. Impact windows and sliders throughout, plus new hardie-board siding. Don't miss out on the chance to affordably obtain your beach house dream goal on this one-of-a-kind island!
Captiva Palma, 4551 Bartlett Pkwy, Upper Captiva, Florida 33924, image 1
$799,000
  • 3 Beds
  • 21/2 Baths
  • 1,722 SqFt
  • $464/SqFt
High-End
House for sale in Captiva Palma
4551 Bartlett Pkwy, Upper Captiva, FL 33924
Recently reduce price makes this one of the best homes available on the island. Just steps from the beach, nestled in sea grape trees and cabbage palms, surrounded by nature. The upside-down floor plan makes for cooler sleeping at night and more breezes during the day. There are screened porches off the master bedroom and the second bedroom which provides for a greater sense of spaciousness. The open deck off the third bedroom can be used as a private entry for guests. The second level has an open floor plan comprised of the living room, dining area, kitchen and half bath, great for a comfortable lifestyle and entertaining. Second floor also has a screened porch off the living area and an open deck off the kitchen; one can follow the sun or hide from the sun. The tower has a spectacular view of the island and gulf. Seller is the original owner, and the home has not been in a rental program. For more privacy the lots east and south of the home are available for additional consideration. There is also a safety harbor club membership available with major benefits including dockage, pool, club house, tennis, trash collection. The club can also provide maintenance staff including yard service home repairs and pest control. Please ask for further information concerning membership cost, application, transfer fees and dues.
North Captiva Sands, 140 Mourning Dove Dr, Upper Captiva, Florida 33924, image 1
$705,000
  • 2 Beds
  • 2 Baths
  • 1,051 SqFt
  • $671/SqFt
High-End
House for sale in North Captiva Sands
140 Mourning Dove Dr, Upper Captiva, FL 33924
Authentic old florida island charm and timeless appeal combine in this beautiful 2-bedroom cottage, offering classic character with thoughtful updates, including a new metal roof installed in 2023. Inside, soaring cathedral tongue-and-groove ceilings, oak floors, and rich pecky cypress walls create a warm and inviting atmosphere. The open-concept layout was ahead of its time, featuring a spacious kitchen with a wraparound dining bar that flows into the living and dining areas. All living spaces open to an oversized covered front porch, perfect for relaxed outdoor living. The primary suite features glowing wood finishes and an en-suite bathroom with a tub/shower combination. The second bedroom offers dual closets and a cozy nook for more storage or decor, making it ideal for accommodating guests with comfort and style. Below the house, a shady wood deck offers a great space for grilling and entertaining. An adjacent enclosed room houses a full laundry area and extra storage. The landscaped front yard features native plantings and a curving paver driveway. This home enjoys a prime location close to the ferry landing, just a short golf cart ride to both the gulf's sandy shoreline and the bayside beaches along pine island sound. Boating, fishing, shelling, and island exploration are all easily accessible from this quiet, scenic spot. This charming cottage offers the best of island living—historic style, modern comforts, and one of the best floor plans of a house this size on the island... All in a setting that captures the magic of north captiva. Whether you're seeking a peaceful getaway, a year-round retreat, or a vacation rental to offset costs while you enjoy the island lifestyle, this is a rare opportunity to own a genuine piece of north captiva's heritage.
Castaway Key, 4460 Smugglers Dr, Upper Captiva, Florida 33924, image 1
$1,425,000
  • 4 Beds
  • 3 Baths
  • 2,358 SqFt
  • $604/SqFt
Mid-Tier
House for sale in Castaway Key
4460 Smugglers Dr, Upper Captiva, FL 33924
Just move right in to this fully remodeled, turn-key, luxury north captiva estate home with pool! This four-bedroom, three-bath island gem offers elegance, space, comfort, and modern design. The great room features an expansive tv area, dining area, luxury kitchen, and a large sundeck with grilling/dining areas overlooking the huge private heated pool. Reminding you of every shade of blue shimmering in the waters along the beach and sunny captiva skies, this chef's kitchen will impress you with all new stainless steel appliances, custom-designed cabinetry, glistening white solid surface countertops, and an island layout with a built-in dining bar. The kitchen might become your favorite place! Just off the living space is a convenient guest bedroom surrounded by windows and beautiful views of the swaying palm trees. A full bath with a custom tile shower and glass door enclosure is just around the corner for convenient access from the living room and upstairs guests. The primary suite is a true retreat with a private sun deck, spa-like en suite bath, a stunning freestanding oval soaking tub set in a bay window alcove, a custom mosaic-tiled walk-in shower, and dual vanities. The other two guest bedrooms and guest bath on that level offer plenty of sleeping spaces for large families or groups. The outdoor entertainment area is a true oasis, boasting a giant pool, poolside tv area, pool bar, and outdoor shower. Perfect for entertaining or just unwinding in paradise. Clad with hardie board and upgraded with new impact-resistant windows, sliding glass doors, and a standing seam aluminum roof, this home is built for beauty and resilience. It is just a short walk or golf cart ride from pristine beaches, the ferry, and the resort area. This home feels like a new home and is priced far below construction value. Fantastic potential to generate high rental revenue. This house is a must-see if you have been looking for a newer, larger pool home. An excellent opportunity to combine family vacation fun with high rental revenue while you are away!
Safety Harbor Club, 370 Townhouse Ln #65, Upper Captiva, Florida 33924, image 1
$589,900
  • 3 Beds
  • 2 Baths
  • 979 SqFt
  • $603/SqFt
Mid-Tier
Townhouse for sale in Safety Harbor Club
370 Townhouse Ln #65, Upper Captiva, FL 33924
Welcome to sandy toes villa, where owning a piece of southwest florida paradise means trading traffic and busy streets for sandy paths, golf-cart rides, pristine beaches and true island living. Located on the exclusive, boat-access-only north captiva island, this beautifully updated 3-bedroom, 2-bath townhome offers the perfect combination of island getaway and proven vacation rental investment. Offered fully furnished and turnkey, sandy toes features impact windows and doors, tile flooring throughout, granite countertops, stainless steel appliances and tasteful updates throughout. Enjoy beautiful water views from the private lanai and easy access to the island’s beaches, with a golf cart available for purchase separately. Owners and guests enjoy access to the safety harbor club and island club, with pools, tennis, pickleball, private beach access, kayaks, paddleboards, bikes and marina access. North captiva also offers its own laid-back dining scene, including mango’s bar & grill, over the waterfront and mainstay/barnacles, along with a private landing strip serving small aircraft—adding to the island’s truly unique accessibility and charm. Already established in a successful vacation rental program with $60, 000+ in annual rental income, sandy toes offers the opportunity to own a piece of north captiva while generating income when you're away. Barefoot beach days, boating, fishing, golf-cart adventures, waterfront dining and spectacular sunsets—this is southwest florida island living at its best! *check out the virtual tour*
Safety Harbor Club, 4470 Seagrape Bend Dr, Upper Captiva, Florida 33924, image 1
$995,350
  • 3 Beds
  • 2 Baths
  • 1,500 SqFt
  • $664/SqFt
Mid-Tier
House for sale in Safety Harbor Club
4470 Seagrape Bend Dr, Upper Captiva, FL 33924
2022 construction. Private interior elevator. Never rented. Very low insurance costs. Safety harbor club. A different kind of north captiva opportunity. Built in 2022, never rented and exceptionally lightly used, this thoughtfully designed 3-bedroom island home combines newer construction, a private interior elevator, and meaningful ownership advantages-all offered under $1 million. Start with the practical differences. Current property insurance costs are very low, and the home has seen very limited occupancy without the wear associated with vacation-rental use. The private interior elevator with vestibule, wide clearances, lever handles, and front-control appliances make the home particularly well suited for multigenerational living and/or aging in place. Designer kohler fixtures, a stylish upgraded kitchen, designer lighting, and a recessed electric fireplace complement the interior. Outside, enjoy a roof deck with gulf and sound view corridors, a new hot tub, an under-house entertaining deck with a custom cedar bar, professionally planned landscaping, and buried propane serving the on-demand water heater and gas range. Safety harbor club membership provides a newly renovated private community pool about 200 feet from the house, plus private community dockage and beach access about 1, 000 feet away. Current dues include water, upgraded wastewater/sewer service, trash pickup, community amenities, and access to full-time on-site staff. Nearly new. Never rented. Interior elevator. Low insurance and maintenance costs. Safety harbor club services & amenities. Offered below $1 million. For buyers wanting newer construction under $1 million on north captiva, this is one to see now. Schedule a private showing and compare what 4470 seagrape bend offers.
North Captiva Dunes, Upper Captiva, Florida 33924, image 1
$150,000
  • 0.2 Acres
  • $750,000/Acre
High-End
Land for sale in North Captiva Dunes
Undisclosed Address, Upper Captiva, FL 33924
Amazing opportunity to build your dream vacation paradise. Arrive by sea or air to your private home in upper captiva island. Just steps away to multiple beach access areas and an abundance of preserve land to explore. This piece of paradise will afford a perfect setting for nature enthusiasts.
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