Upper Captiva Homes with Gulf Waterfront

Upper Captiva Homes with Gulf Waterfront

Welcome to Upper Captiva, Florida – a hidden gem nestled in Lee County, where the pristine beauty of the Gulf of Mexico meets the charm of a close-knit island community. This enchanting destination offers a unique blend of natural beauty and tranquil living, making it an ideal choice for those seeking a serene escape or a permanent home.

Upper Captiva is known for its breathtaking Gulf waterfront properties, where residents can indulge in stunning sunsets and soothing ocean breezes right from their backyards. Imagine waking up to the sound of gentle waves lapping against the shore and the sight of dolphins dancing just beyond your door. Homes here are designed to maximize the beauty of their surroundings, with spacious decks and expansive windows that invite the outside in.

The island boasts a relaxed lifestyle, where golf carts replace cars, and sandy pathways lead to secluded beaches. Residents enjoy a plethora of outdoor activities, from kayaking and paddleboarding to fishing and beachcombing. The vibrant local community is filled with friendly faces, and the island's limited development ensures that the natural landscape remains untouched, providing a peaceful retreat from the hustle and bustle of everyday life.

Whether you're looking for a vacation getaway or a permanent residence, Upper Captiva's Gulf waterfront homes offer a unique opportunity to embrace island living at its finest. Experience the tranquility, beauty, and charm of this idyllic paradise – your dream home awaits!

Newest Upper Captiva Homes with Gulf Waterfront

$1,245,000
3 Beds ⋅ 2 Baths ⋅ 2026020806 MLS
541 Gulf Lane – Steps to the Sand with Sweeping Water Views & Resort-Style Outdoor Living.  This retreat offers the kind of beachside life that feels effortless from the moment you arrive. This beautifully positioned 3-bedroom, 2-bath half-duplex captures spectacular water views from every level, making the Gulf part of your everyday backdrop—from morning coffee to sunset unwinding. Designed for relaxed coastal living, this getaway features a bright, open gathering space filled with natural light and framed by views of the Gulf and sunsets. The living, kitchen, and dining zones are beautifully decorated and fully furnished. The primary suite offers a peaceful private escape, complete with a jetted soaking tub—perfect for relaxing after sun-filled beach days and evening walks along the shore. On the second level, the large guest room offers fantastic water views and a private sun deck facing the Gulf. A third guest bedroom is just around the corner, tucked into the eaves, sharing a large guest bath with a tub/shower combo. Outside is where property truly comes to life. A private pool and hot tub, expansive sun deck, and poolside bar create a resort-like setting designed for entertaining, relaxing, and making memories with family and friends. A convenient ground-level 1/2 bath and a dedicated laundry area make transitions from the beach to the pool effortless. Set along one of North Captiva's most desirable beachside lanes at a really high elevation, the home offers immediate access to the Gulf's sugar-sand shoreline, with its separate 1/2-interest in a deeded beach access lot. Whether you're seeking a personal island getaway, a vacation rental investment, or a place to gather for years to come, 541 Gulf Lane delivers the rare combination of location, views, and the laid-back luxury that defines North Captiva living. The adjacent 1/2 Duplex (543 Gulf Ln) is also available for purchase so that you can own the entire property!

541 Gulf Lane, 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
$1,245,000
3 Beds ⋅ 3 Baths ⋅ 2025026081 MLS
Island Paradise Found: Gulf-Side Retreat with Private Hot Tub/Pool & Tiki Bar! Wake up to your dream beach paradise on North Captiva Island! This exceptionally well-maintained 3-bedroom, 2.5-bath 1/2 duplex oasis offers unbeatable views and amenities designed for luxurious island life. Step inside to an open-concept living area featuring vaulted ceilings, bright coastal décor, a spacious kitchen with granite countertops & stainless steel appliances, plus a counter-height dining bar. This seamless space connects effortlessly to the front porch and sunset deck, providing the perfect venue for gazing at the shimmering Gulf. The primary suite on the main level offers a spa-style bath with a soaking tub and dual vessel sinks. The upper-level main bedroom enjoys panoramic Gulf views and its own private sun deck—a front-row seat to palm trees, pristine sandy beach, and glowing sunsets followed by moonlit water. A charming bunk room comfortably sleeps three, ideal for kids or grandkids. Your private outdoor oasis is an entertainer's dream, complete with a heated pool/spa combo, covered tiki bar, ground-level laundry, half bath, and a grilling station. Built for durability and peace of mind, the home boasts mostly Hardie board siding, a metal roof, and impact-rated doors and windows. A 1/2 interest in a membership to the deeded beach lot across the street ensures a direct connection to the sand and surf. If you are looking for the ultimate island beach retreat with excellent rental potential, 543 Gulf Lane offers unparalleled charm, comfort, and an unbeatable location at a price.

543 Gulf Lane, Upper Captiva
$3,499,000
225027495 MLS
HEAVEN ON EARTH! An exceptional and rare opportunity to own an almost full acre of beachfront property with bay to gulf access on North Captiva Island with access via boat, ferry, airplane or helicopter. One of a kind property located in pure paradise with white sandy beaches, endless million dollar sunset views and engineered plans for a gorgeous new home are also available to view. This is a golf cart only island with access to some of the best fishing, nature walks, water recreation activities on five miles of sandy beaches - you can walk or ride your beach bike all the way to Red Fish Pass with incredible shelling, beaches and waters. Lots of activities available - swim at Mangos and enjoy cocktails or relax - Barnacles offers great food, outdoor games and Over the Waterfront Restaurant is a quaint place to enjoy a great lunch or dinner. The North Captiva Island Club and Safety Harbor offers memberships for tennis/pickleball/swimming and more. Live your best life in a wonderful oasis - laid back lifestyle - located within minutes by water to Useppa Island, just south of Cayo Costa, Cabbage Key and a vibrant nature wonderland with daily sightings of dolphins, manatees, birds and more. Build the plans Seller has or create your own dream home. Only three hundred homes, more than half of the Island is a State Park. Minutes away is Pine Island which offers a ferry transport out to the island every two hours during the day! This is your time, your moment to grab a priceless piece of property and live your best life!

4281 Point House Trail, 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
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