Refine Search
Map
Sort by
$1,450,000
4 Beds ⋅ 4 Baths ⋅ 2026030979 MLS
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.

4490 Oyster Shell Drive, Upper Captiva
$1,300,000
3 Beds ⋅ 3 Baths ⋅ 2026013122 MLS
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.

4510 Oyster Shell Drive, Upper Captiva
$3,895,000
4 Beds ⋅ 5 Baths ⋅ 2026007775 MLS
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!

660 Gulf Lane, Upper Captiva
$819,000
2 Beds ⋅ 3 Baths ⋅ 2025018406 MLS
With Fantastic Gulf Views and a Prime Location just 350 feet from the beach, this island-style vacation retreat stands out with its extra charm and character!  Located alongside North Captiva's private airstrip, which gives the home an excellent view corridor.  Great for pilots and beachgoers alike!  Imagine gazing at the water from your living room and sun deck, then relaxing after a day at the beach in your beautiful pool while listening to the sounds of the surf.  Step inside and discover a 2-bedroom, 2.5-bath layout designed for relaxed island living. Top-level painted wood cathedral ceilings give this beachy bungalow a feeling of a much larger home, and with island flair. Abundant natural light pours in through multiple Gulf-facing French doors along the sundeck, truly bringing the outside in for sunset time! The open-concept living and dining area also features a fireplace as a focal point, while the kitchen offers modern cabinetry, solid-surface countertops, and stainless steel appliances. The primary suite includes an en-suite bath with a combined tub & shower, plus direct access to a private balcony for enjoying Gulf breezes. The guest suite is equally inviting, with its own private bath and French doors opening onto the covered screen porch. This hidden gem is a rare combination of proximity to the sugar sand beaches, poolside relaxation, and real island character at an affordable price point!

210 White Pelican Drive, Upper Captiva
$3,250,000
4 Beds ⋅ 5 Baths ⋅ 225035699 MLS
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!

4620 Oro Pesos Lane, Upper Captiva