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$624,900
2 Beds ⋅ 1.5 Baths ⋅ 2026039278 MLS ⋅ Castaway Key Unrecorded Subdivision BLDG.
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!

4561 Smugglers Dr, Upper Captiva
$170,000
2026035553 MLS ⋅ Castaway Key Unrecorded Subdivision BLDG.
Build Your Island Dream Home at 4471 Cutlass Dr on North Captiva Island, FL! Discover this opportunity to build your custom retreat on one of North Captiva's desirable streets. This high and dry lot offers the perfect canvas for your island vision, with a private well worth 25k-40k already in place to give you a head start on construction. The higher elevation offers a safe foundation for creating the home you've always imagined. Just a quick golf cart ride away are multiple beach access points, putting you within moments of the Gulf's sugar-sands or the preserve's hidden beaches and trails. Whether you're into shelling, hiking, kayaking, or simply soaking in the sunsets, you'll be surrounded by untouched natural beauty every day. The location also places you close to the resort area, with pools, tennis, shops, dining, and the ferry landing. That makes it ideal not only for an ultimate vacation retreat, but also for potential future rental income. With its beautiful location, existing well, and proximity to both the nature preserve and resort-style amenities, this lot is more than just a plot of land - it's your chance to design the island lifestyle most people only dream of.

4471 Cutlass Dr, Upper Captiva
$156,000
2026034990 MLS ⋅ Castaway Key Unrecorded Subdivision BLDG.
Build your North Captiva dream home on this oversized 100' x 120' homesite located in a desirable higher-elevation area just five rows back from the Gulf! With approximately 0.28 acres of land, this generous parcel provides all the extra space needed to create your ideal custom vacation retreat, pool, outdoor entertaining areas, and lush landscaping. The property is close enough to the Gulf to enjoy the sounds of the surf, with convenient beach access leading to miles of beautiful sandy shoreline just a short golf cart ride away. A properly designed island home may offer the opportunity to capture Gulf and Bay views from upper living levels or a lookout deck, adding another dimension to this already appealing location. Spend your days walking the beach, shelling, swimming, exploring nearby preserve lands, or simply enjoying the slower pace of North Captiva. Island dining, shopping, ferry service, and resort amenities are all easily reached by golf cart. North Captiva is a private, boat-access-only barrier island known for its uncrowded beaches, abundant wildlife, protected natural areas, and distinctive golf-cart lifestyle. If you are looking for a high-elevation, oversized property with a view, don't miss this lot!

4531 Conch Shell Dr, Upper Captiva
$595,000
2026023733 MLS ⋅ Castaway Key Unrecorded Subdivision BLDG.
An incredibly rare opportunity on North Captiva Island! This collection of 4 adjacent lots spans a generous 1.13 acres, offering unmatched potential for a private estate with tropical gardens, a multigenerational retreat, or a 4-residence sanctuary. Enjoy exceptional privacy and the potential for sweeping bay and preserve views from upper levels over and around just 1 row of homes. Ideally located near island dockage, the ferry landing, and club amenities, this property combines seclusion with convenience. Lots may be purchased individually or as a tailored collection that fits your vision.

4430 Conch Shell Dr, Upper Captiva
$1,299,000
3 Beds ⋅ 3.5 Baths ⋅ 2026023102 MLS ⋅ Castaway Key Unrecorded Subdivision BLDG.
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.

621 Rum Rd, Captiva
$1,425,000
4 Beds ⋅ 3 Baths ⋅ 2026021059 MLS ⋅ Castaway Key Unrecorded Subdivision BLDG.
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!

4460 Smugglers Dr, Upper Captiva
$1,395,000
3 Beds ⋅ 3.5 Baths ⋅ 2026011545 MLS ⋅ Castaway Key Unrecorded Subdivision BLDG.
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.

4541 Conch Shell Dr, Upper Captiva
$3,895,000
4 Beds ⋅ 4.5 Baths ⋅ 2026007775 MLS ⋅ Castaway Key Unrecorded Subdivision BLDG.
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 Ln, Upper Captiva
$78,000
2026005346 MLS ⋅ Castaway Key Unrecorded Subdivision BLDG.
Tropical interior lot on the private and serene North Captiva Island, with miles of pristine beaches and vacation amenities. This location is conveniently located within a short golf cart ride to the resort hub area with pools, dining, shopping, boat rentals, and the ferry landing. Just 1600 feet to the nearby state-owned beach access. It is time for you to start planning your new island beach retreat!

4490 Schooner Dr, Upper Captiva
$450,000
225033168 MLS ⋅ Castaway Key Unrecorded Subdivision BLDG.
Very rare opportunity to purchase a vacant land parcels on the southernmost North Captiva Island canal bordering the state preserve! A well-designed home's upper levels will offer unobstructed views across the state wildlife reserve to Pine Island Sound, plus vistas over the entire preserve and island to the Gulf for beautiful sunsets. It is located adjacent to a neighborhood HOA double-sized parcel at the end of the canal, which offers extra green space to the south. If you are looking for great views, private dockage for multiple boats, and privacy while close to the beach, this lot may be the one for you!

671 Rum Rd, Upper Captiva