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$589,900
3 Beds ⋅ 2 Baths ⋅ 2026040242 MLS
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*

370 Townhouse Lane Unit 65, Upper Captiva

$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

$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