Castaway Key Unrecorded Subdivision - Upper Captiva Florida Homes for Sale

2026035553 MLS

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 Drive, Upper Captiva

Listing Courtesy of Resort Properties Internationa

$156,000

2026034990 MLS

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 Drive, Upper Captiva

Listing Courtesy of Resort Properties Internationa

$595,000

2026023733 MLS

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 Drive, Upper Captiva

Listing Courtesy of Resort Properties Internationa

$1,425,000

4 Beds ⋅ 3 Baths ⋅ 2026021059 MLS

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 Drive, Upper Captiva

Listing Courtesy of Resort Properties Internationa

$974,000

3 Beds ⋅ 4 Baths ⋅ 2026014378 MLS

Exceptional Double-Lot Island Retreat! Ideally positioned on a rare double lot, this beautifully maintained North Captiva Island home offers enhanced privacy, extra space, and low-maintenance coastal living. This North Captiva retreat offers more than just a home; it presents a rare opportunity for the lucky buyer to own an exclusive separate membership in Captiva Castaway Beach. Just a short, scenic stroll from your front door, this membership grants you deeded access to arguably the finest 'sugar sand' private beach on the island. Enjoy this ultimate Gulf-front luxury beach with its pristine, secluded shoreline reserved for a select few, ensuring your piece of paradise remains private and protected for years to come. Designed with a reverse floorplan, the home is filled with natural light and opens to lush tropical surroundings. The main living area, with its full-length sliding glass wall, allows the inside to flow seamlessly onto a spacious screened lanai (with premium “no-see-um” screen comfort) for bug-free open-air entertaining, lounging on the double hammock, or just enjoying the soft gulf breezes, creating indoor-outdoor living ideal for any occasion. The galley-style kitchen features a generous dining bar and walk-in pantry, while two private primary suites with en-suite baths and walk-in showers offer comfort and privacy. A versatile bunk room serves as a fourth sleeping area for additional guests. Extensive exterior “maintenance-free” recent upgrades set this home apart: impact-resistant doors and sliders, PGT energy-efficient low-E impact windows, composite decking, powder-coated aluminum railings, and premium composite siding (rated for up to 150-mph winds) that you never need to paint! Additional improvements include a new roof with transferable warranty, energy-efficient HVAC systems with Wi-Fi thermostats, and updated appliances—delivering durability and low-maintenance ownership so you can spend more time on the beach and less time working on your house. Let your imagination wander! Create your personalized island paradise, as the adjacent surveyed lot, cleared free of Brazilian pepper, provides valuable flexibility—ideal for lush gardens, a swimming pool, a 2nd guest house or creating an even larger private compound. Conveniently located near the beach access, ferry landing, and island amenities, this property has a history of strong rental potential. A rare opportunity to own a double-lot island home with upgrades, privacy, and expansion potential—all offered well below reconstruction cost. Schedule your private showing today and experience the island lifestyle firsthand!

4511 & 4501 Schooner Drive, Upper Captiva

Listing Courtesy of Resort Properties Internationa

Selling Office: .

$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

Listing Courtesy of Resort Properties Internationa

$78,000

2026005346 MLS

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 Drive, Upper Captiva

Listing Courtesy of Resort Properties Internationa

$1,595,000

4 Beds ⋅ 4 Baths ⋅ 2025019622 MLS

Elegant Gulf View Estate with Pool on Oversized Lot! Located just one roof line from the Gulf, this impressive North Captiva Island home is spacious & luxurious. Its 4 bedrooms & 3.5 baths provide plenty of room for family & friends. This island getaway is situated on an extra-large corner lot, offering enhanced privacy and excellent view corridors. The upper level offers the ultimate open-concept floor plan, anchored by a designer chef's kitchen featuring a large storage-and-prep island, a full dining bar, expansive custom cabinetry, quartz countertops, and stainless steel appliances. The great room is wrapped in bright, crisply painted shiplap, evoking the breezy elegance of a true island-style beach home. The large, covered connecting porch with Gulf-facing views is perfect for watching sunsets and sipping margaritas. This thoughtfully designed home offers two private master suites, each with its own walk-in shower, double vanities, and spacious layout for peaceful retreats. On the first level, two additional bedrooms and a shared bath provide ample space for guests; one could be considered a mini-primary bedroom with access to a large covered porch facing the pool, and the other a spacious bunk room that sleeps 5+, perfect for large families or rental groups. Other highlights include a package lift/elevator for effortless luggage and grocery transport to the upper floors, unique wood-grain tile floors, beautifully appointed bathrooms, and charming coastal décor throughout. This home is exceptionally well-designed and ready to be tailored to your style and rental needs. Outside, the lower-level lounge, dining, entertaining, and sundeck areas cover most of the home's footprint, offering fantastic opportunities for shady spots and sunny perches. The private heated pool resides amongst mature tropical trees with plenty of room for all to lounge the day away in the sun! Updated in 2021 with new impact windows/doors & hardie board siding. The ferry landing, club pool, tennis courts, dining, and shops are all just a quick golf cart ride away. With its prime location, Gulf views, high-end finishes, extra-large lot size, and character, this home offers a rare opportunity to own an estate home on the south side of the island near the sparkling Gulf waters, where you can watch the stunning sunsets every night from your dream home!

4560 Conch Shell Drive, Upper Captiva

Listing Courtesy of Resort Properties Internationa

$1,381,500

3 Beds ⋅ 4 Baths ⋅ 2025005189 MLS

Your Private Island Waterfront Escape — Where Every Sunrise Feels Like It’s Just for You! Imagine waking up to the first blush of sunrise spilling over Pine Island Sound, the sky glowing pink and gold, while you sip coffee on your upper deck with panoramic views over a protected nature preserve. Just the soft rustle of palm fronds, the call of shorebirds, and the quiet lapping of water against your private dock. This isn’t just a house — it’s a 4-sleeping room, 4-bath sanctuary built in 2020 to the highest storm and structural codes, so you can relax knowing your island retreat is as strong as it is beautiful. Inside, light pours in through vaulted ceilings onto airy, coastal-inspired living spaces. The designer kitchen — quartz countertops, stainless appliances, and custom cabinetry — was made for both sunset dinner parties and barefoot brunches after a morning swim. Built with impact windows, Hardie board siding, and a metal roof, this home is built to withstand the elements. Step outside, and your world opens to a screened, heated pool surrounded by lush native landscaping that melts into the untouched preserve. When the day calls for adventure, your dock on a peaceful canal is ready for your boat, with quick access to some of the best fishing waters in Florida. Whether you’re searching for a top-performing vacation rental or a personal hideaway that earns its keep when you’re away, this home is already a proven income generator — and it comes turnkey, so you can start living (or renting) the dream on day one. Opportunities for move-in waterfront properties don’t pop up on North Captiva Island very often — especially ones that offer this level of privacy, views, and modern construction. The only question is: will you let someone else watch your sunrise? Call today before this one disappears over the horizon.

631 Rum Road, Upper Captiva

Listing Courtesy of Resort Properties Internationa

Selling Office: .

$95,000

2025005806 MLS

Oversized corner lot bordering Rum Rd. Just steps from club amenities, shopping, dining, and the ferry landing. Prime view corridor offering Bay and Harbor Views from the highest levels!

4431 Schooner Drive, Upper Captiva

Listing Courtesy of Resort Properties Internationa

Selling Office: .

$1,350,000

4 Beds ⋅ 3 Baths ⋅ 225023035 MLS

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. 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 Drive, Upper Captiva

Listing Courtesy of Resort Properties Internationa

Selling Office: .

$85,000

224064979 MLS

Oversized corner lot bordering Rum Rd. Just steps from club amenities, shopping, dining, and the ferry landing. Bay and Harbor Views from the highest levels! 2 adjacent lots on Schooner Dr. also available. Make an offer today!

4430 Smugglers Drive, Upper Captiva

Listing Courtesy of Resort Properties Internationa

Selling Office: .

$450,000

225033168 MLS

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 Road, Upper Captiva

Listing Courtesy of Resort Properties Internationa

$712,000

2 Beds ⋅ 2 Baths ⋅ 223085813 MLS

Discover the allure of this captivating Island Getaway boasting two bedrooms, two baths, and a secluded Private Pool—all within a short walk from the nearby beach access. Great outdoor space with an expansive screen porch spanning the entirety of the house. Recently outfitted with a new roof. Enjoy proximity to the Island Club's resort-style amenities, the convenient ferry landing, shopping conveniences, and an array of additional attractions. Everything you need to start island-style living now!

4521 Schooner Drive, Upper Captiva

Listing Courtesy of Resort Properties Internationa

Selling Office: .

$1,002,000

4 Beds ⋅ 3 Baths ⋅ 223070254 MLS

Escape to paradise with this fantastic 4-bedroom, 3-bathroom home conveniently between beach access and island club amenities! This stunning property boasts a spacious and open great room, dining, and kitchen area. Perfect for entertaining. Relax in the screen-caged pool area with its convenient wet bar, or enjoy a peaceful evening on the screened porch off the living room. The rooftop lookout deck offers picturesque views of the island's surroundings. Included in the list price is a 1/4 ownership interest of the lot adjacent to the property, offering an excellent protected privacy buffer. Just a short walk to pools, pool bar, store, restaurant, and ferry landing. This home is the perfect blend of relaxation and convenience. Great rental potential. Offset your costs while you enjoy all the island has to offer!

4510 Schooner Drive, Upper Captiva

Listing Courtesy of Resort Properties Internationa

Selling Office: .

$130,000

223043518 MLS

Oversized corner lot on gorgeous North Captiva Island with bay views from the lookout level! Fully cleared and ready to build. New home plans are also available for a 3-bedroom home. Just a short walk to resort areas, ferry landing, and restaurants. Take a quick golf cart ride to miles of gulf beaches or a 1000ft walk down the street to scenic hiking/biking trails throughout the wildlife preserve lands to Gulf beaches.

4430 Cutlass Drive, Upper Captiva

Listing Courtesy of Resort Properties Internationa

Selling Office: .

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Castaway Key Unrecorded Subdivision - Upper Captiva, FL Homes for Sale

Are you looking to buy or sell a home in Castaway Key Unrecorded Subdivision Upper Captiva Florida? Call or Text (239) 880-8850 to schedule a showing on any Castaway Key Unrecorded Subdivision Upper Captiva, FL home for sale or to sell your Castaway Key Unrecorded Subdivision Upper Captiva Florida home! As Realtors specializing in the Castaway Key Unrecorded Subdivision Upper Captiva area, we can take care of all of your Castaway Key Unrecorded Subdivision Upper Captiva FL real estate needs including buying pre-existing homes, new construction homes, condominiums, land, commercial and multi-family homes in Castaway Key Unrecorded Subdivision Upper Captiva Florida. We can also help you find distressed properties in Castaway Key Unrecorded Subdivision Upper Captiva including HUD Homes, Short Sales and REO Bank Foreclosures. If you need help financing a home in Castaway Key Unrecorded Subdivision Upper Captiva, we have access to some of the best lenders that service the Castaway Key Unrecorded Subdivision Upper Captiva Florida area, including lenders that offer credit repair to buy a home and work with home builders in and near the Castaway Key Unrecorded Subdivision Upper Captiva area to help you build your home while building up your credit. If you are going to buy or sell a home in Castaway Key Unrecorded Subdivision Upper Captiva Ohio, then be sure to Call or Text (239) 880-8850 Today! We are a real estate team specializing in the Castaway Key Unrecorded Subdivision Upper Captiva, FL area! Displayed are homes for sale in Castaway Key Unrecorded Subdivision Upper Captiva, FL, a Subdivision located in Upper Captiva Florida. These Castaway Key Unrecorded Subdivision Upper Captiva Listings are updated every 15 minutes from the Upper Captiva MLS.