Upper Captiva Homes with Deck Exterior

Upper Captiva Homes with Deck Exterior

Welcome to Upper Captiva, a hidden gem nestled in the heart of Lee County, Florida. This idyllic island community, accessible only by boat or ferry, offers an unparalleled escape from the hustle and bustle of everyday life. With its pristine beaches, crystal-clear waters, and lush natural surroundings, Upper Captiva is the perfect destination for those seeking tranquility and adventure alike.

One of the standout features of homes in Upper Captiva is their charming deck exteriors. Imagine sipping your morning coffee or watching the sunset from your own private deck, surrounded by the soothing sounds of the ocean and the gentle rustle of palm trees. These outdoor spaces are not just an extension of your home; they are a sanctuary for relaxation and entertainment. Whether you're hosting a barbecue with friends or enjoying a quiet evening under the stars, the deck is the perfect place to create lasting memories.

The homes in Upper Captiva are designed to embrace the island lifestyle, with open floor plans, large windows, and outdoor living spaces that seamlessly blend indoor and outdoor environments. Many properties feature stunning views of the Gulf of Mexico, providing a picturesque backdrop for your everyday life.

Beyond the beautiful homes, Upper Captiva is a paradise for outdoor enthusiasts. With opportunities for fishing, kayaking, and exploring the island's natural beauty, residents can enjoy a lifestyle that is both active and serene. Come discover Upper Captiva, where your dream home awaits, complete with a deck that invites you to savor every moment in this tropical oasis.

Newest Upper Captiva Homes with Deck Exterior

4470 Seagrape Bend Drive, Upper Captiva
$995,350
3 Beds ⋅ 2 Baths ⋅ 2026040980 MLS
2022 CONSTRUCTION. PRIVATE INTERIOR ELEVATOR. NEVER RENTED. VERY LOW INSURANCE COSTS. SAFETY HARBOR CLUB. A different kind of North Captiva opportunity. Built in 2022 to the building codes in effect at the time of construction, never rented and exceptionally lightly used, this solidly built, 3-bedroom island home combines newer construction, a private interior elevator and meaningful ownership advantages—all offered under $1 million. Start with the practical differences. Current property insurance costs are very low and the home has seen very limited occupancy without the wear associated with vacation-rental use. The private interior elevator with vestibule, wide clearances, lever handles and front-control appliances make the home particularly well suited for multigenerational living and aging in place. Designer Kohler fixtures, designer lighting and a recessed electric fireplace complement the interior. Outside, enjoy a roof deck with Gulf and Sound view corridors, new hot tub, under-house entertaining deck with custom cedar bar, professionally planned landscaping and buried propane serving the on demand water heater and stove. Safety Harbor Club membership provides access to private community boat dockage, tennis/pickleball courts and beach access approximately 1,000 feet away. A direct walking path connects the home to the newly renovated private community pool, approximately 200 feet away. Current $575/month club dues include water, upgraded wastewater/sewer service, trash pickup, community amenities and access to full-time onsite staff. Nearly new. Never rented. Interior elevator. Low insurance and maintenance costs. Safety Harbor Club. Offered below $1 million. For buyers wanting newer construction under $1 million on North Captiva, this is one to see now. Schedule a private showing and compare what 4470 Seagrape Bend offers.

4470 Seagrape Bend Drive, Upper Captiva
370 Townhouse Lane Unit 65, Upper Captiva
$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
201 White Pelican Drive, Upper Captiva
$799,000
2 Beds ⋅ 3 Baths ⋅ 2026037638 MLS
Escape to the laid-back charm of Old Florida with this elevated island retreat on beautiful North Captiva, located less than 300 feet from the beach—just steps from the sand and Gulf waters. This unique property also includes an adjoining lot, providing exceptional flexibility for a future pool, expansion of the existing home, or construction of an additional residence. The main home features one bedroom, two bathrooms, and a versatile den that can easily serve as a second bedroom, while the ground-level apartment offers an additional bedroom and bathroom—perfect for guests, extended family, or rental use. Multiple outdoor decks provide plenty of space to relax and enjoy the island breeze and partial Gulf views, while several storage buildings offer convenient space for golf carts, beach gear, and island essentials. Accessible only by boat or small plane, North Captiva offers a truly unique car-free lifestyle where golf carts, bicycles, and walking are the preferred ways to get around. Surrounded by nature, pristine beaches, boating, fishing, and strong vacation-rental appeal, this property offers an incredible opportunity to own a versatile piece of island paradise. Schedule your private showing and experience the North Captiva lifestyle for yourself!

201 White Pelican Drive, Upper Captiva
140 Mourning Dove Drive, Upper Captiva
$705,000
2 Beds ⋅ 2 Baths ⋅ 2026034184 MLS
Authentic Old Florida Island Charm and timeless appeal combine in this beautiful 2-bedroom cottage, offering classic character with thoughtful updates, including a new metal roof installed in 2023. Inside, soaring cathedral tongue-and-groove ceilings, oak floors, and rich pecky cypress walls create a warm and inviting atmosphere. The open-concept layout was ahead of its time, featuring a spacious kitchen with a wraparound dining bar that flows into the living and dining areas. All living spaces open to an oversized covered front porch, perfect for relaxed outdoor living. The primary suite features glowing wood finishes and an en-suite bathroom with a tub/shower combination. The second bedroom offers dual closets and a cozy nook for more storage or decor, making it ideal for accommodating guests with comfort and style. Below the house, a shady wood deck offers a great space for grilling and entertaining. An adjacent enclosed room houses a full laundry area and extra storage. The landscaped front yard features native plantings and a curving paver driveway. This home enjoys a prime location close to the ferry landing, just a short golf cart ride to both the Gulf's sandy shoreline and the bayside beaches along Pine Island Sound. Boating, fishing, shelling, and island exploration are all easily accessible from this quiet, scenic spot. This charming cottage offers the best of island living—historic style, modern comforts, and one of the best floor plans of a house this size on the island... all in a setting that captures the magic of North Captiva. Whether you're seeking a peaceful getaway, a year-round retreat, or a vacation rental to offset costs while you enjoy the island lifestyle, this is a rare opportunity to own a genuine piece of North Captiva's heritage.

140 Mourning Dove Drive, Upper Captiva
4490 Oyster Shell Drive, 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
4580 OYSTER SHELL DR & 370 TOWNHOUSE Lane Unit 60, Upper Captiva
$865,000
3 Beds ⋅ 2 Baths ⋅ 2026020831 MLS
Dock your boat and enjoy water views from an end-unit townhome, while you build your dream home on an incredible lot with direct views toward the beach and Gulf! Introducing a unique island ownership combination: Townhome #60 at 370 Townhouse Ln (Parcel ID: 05-45-21-03-00000.0600) in Safety Harbor Club, paired with a separate buildable homesite at 4580 Oyster Shell Dr, offered together as an exceptional package. The townhome offers immediate enjoyment with beautiful harbor views, shared community dockage steps away, and full access to all Safety Harbor Club amenities, including a heated pool, tennis courts, pickleball, clubhouse, dining, convenient ferry landing, and private Gulf beach access. Perfectly positioned within Safety Harbor Club, the townhome provides an ideal home base for boating, beach days, and island living, with rental or personal-use flexibility. Included in this package is 4580 Oyster Shell Dr, a valuable homesite with incredible views!  You will be stunned by the amazing view corridor looking down onto the sugar-sand beach and sparkling Gulf waters beyond.  Imagine watching the sun set every night right from your living room. This lot plus townhome combination is a must-see!

4580 OYSTER SHELL DR & 370 TOWNHOUSE Lane Unit 60, Upper Captiva
4460 Smugglers Drive, Upper Captiva
$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
4481 Escondidio Lane Unit 80, Upper Captiva
$565,000
3 Beds ⋅ 2 Baths ⋅ 2026020799 MLS
Wake Up in Paradise at Sunrise Bay on North Captiva Island! Picture this: the first light of dawn glistens across Pine Island Sound as you sip coffee on your screened porch, watching the world wake up in perfect peace. A gentle sea breeze slips through palm fronds, and within minutes, you can be out the door and onto your docked boat, sandy Gulf shoreline, or quiet nature trail. Sunrise Bay isn't just a townhome - it's your front-row seat to island life. This 3-bedroom, 2-bath townhome has been stylishly updated to deliver modern coastal comfort with a dose of Old Florida charm. Inside, sunlit living spaces, tasteful furnishings, and thoughtful upgrades create a warm, effortless retreat. The townhouse is entirely turnkey, with thoughtfully updated décor and furnishings so you can settle in and start enjoying your new island retreat immediately. Outside, you're just a short hop to the ferry landing, Dock Slips, Over the Waterfront Dining, and endless opportunities to fish, shell, kayak, or relax in total tranquility. For boaters, this property is a dream come true, with community docks that provide easy access to the Gulf for fishing trips, sunset cruises, or island-hopping adventures. If you prefer to keep your toes in the sand, pristine Gulf-side beaches are just a short golf cart ride away, making spontaneous beach visits part of your everyday life. Safety Harbor Club's included resort-style amenities, including the recently updated sparkling heated community pool, tennis & pickleball courts, a clubhouse, and waterfront dining, give you the best of vacation living right at home. Perfect for a personal island hideaway or an income-generating rental, Sunrise Bay blends laid-back luxury with unbeatable convenience. Properties with this level of charm, boat dockage, & water views don't usually last long at this price. Schedule a showing today and claim your place in paradise!

4481 Escondidio Lane Unit 80, Upper Captiva
370 Townhouse Lane Unit 60, Upper Captiva
$470,000
3 Beds ⋅ 2 Baths ⋅ 2026017061 MLS
End Unit With Harbor Views & Dock Access! Experience the tropical island waterfront lifestyle! This value-priced townhome offers shared dockage for your boat, and an unbeatable location just steps from the dockage, ferry landing, and club restaurant… because sometimes the outside is doing all the heavy lifting. Let’s be clear: the interior is authentically, unapologetically vintage. We’re talking original finishes, original fixtures, and décor. The kitchen and baths? Classic. The vibe? Beach Retro. The opportunity? Endless. But here’s the thing—this townhome is livable, functional, and ready for its next chapter. Whether you’re dreaming of a full renovation, a creative reimagining, or simply embracing the throwback charm (we won’t judge), this is your chance to start with a light-and-airy plan in an even better location. And what a location it is—end unit, harbor views, steps to dockage and kayak beach... and just a short distance to everything Safety Harbor Club has to offer. Enjoy access to a heated pool, tennis and pickleball courts, clubhouse dining, and private Gulf beach access where the sunsets are always in style (no renovation required). Bring your vision. Bring your contractor. Or bring your love for 1985. Either way, this is your chance to secure a waterfront foothold in an end unit at a price that leaves room for transformation. Don’t miss this unique before-and-after opportunity.

370 Townhouse Lane Unit 60, Upper Captiva
4510 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
4541 Conch Shell Drive, Upper Captiva
$1,395,000
3 Beds ⋅ 4 Baths ⋅ 2026011545 MLS
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 Drive, Upper Captiva
370 Townhouse Lane Unit 66, Upper Captiva
$490,000
3 Beds ⋅ 2 Baths ⋅ 2026010833 MLS
Priced to Sell! Positioned directly on the harbor in Safety Harbor Club, this waterfront townhome offers one of the most convenient dockside locations on North Captiva Island. With the boat docks less than 50 feet from your door, this home is ideal for those who want immediate access to boating and waterfront living. The layout is designed to capture excellent harbor views while providing comfortable island living. Light-filled interior spaces flow naturally to the outdoor covered screen porch, where you can watch boats come and go and enjoy the serene waterfront setting. As part of Safety Harbor Club, owners enjoy a full suite of amenities including a community pool, tennis & pickleball courts, clubhouse, on-site dining, & Gulf beach access. The nearby ferry landing makes travel simple while maintaining the peaceful, car-free charm of North Captiva. Whether used as a personal retreat or investment property, this harborfront townhome offers an exceptional combination of location, lifestyle, and boating convenience on one of Florida’s most unique barrier islands. There is a tenant currently in place until July 31, 2026.

370 Townhouse Lane Unit 66, Upper Captiva
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