Upper Captiva Homes with Deck Exterior

Upper Captiva Homes with Deck Exterior

Welcome to Upper Captiva, Florida, a hidden gem nestled in Lee County that offers a unique blend of natural beauty and serene coastal living. This idyllic island, accessible only by boat or ferry, is a paradise for those seeking a tranquil escape from the hustle and bustle of everyday life. With its pristine beaches, lush mangroves, and breathtaking sunsets, Upper Captiva is the perfect backdrop for your dream home.

One of the standout features of homes in this charming community is the exquisite deck exteriors. Imagine sipping your morning coffee or enjoying a sunset cocktail on your spacious deck, surrounded by the soothing sounds of the ocean and the gentle rustle of palm trees. These outdoor spaces are designed for relaxation and entertainment, providing the perfect setting for family gatherings, barbecues, or simply unwinding after a long day.

Upper Captiva is not just about the homes; it’s about a lifestyle. The island boasts an array of outdoor activities, from kayaking through the mangroves to fishing in the crystal-clear waters. Explore the unspoiled beaches, take a leisurely stroll along the shoreline, or indulge in a day of sunbathing. With a strong sense of community and a laid-back atmosphere, Upper Captiva is truly a place where you can reconnect with nature and enjoy life at a slower pace.

Whether you’re looking for a vacation retreat or a permanent residence, homes with deck exteriors in Upper Captiva offer an unparalleled living experience. Discover your slice of paradise today and embrace the beauty of island life!

Newest Upper Captiva Homes with Deck Exterior

3 Beds ⋅ 2 Baths ⋅ 2026031138 MLS

Experience the best of coastal living in one of the premier townhomes in Safety Harbor Club! This beautifully updated end-unit offers 3 bedrooms, 2 full baths, and is filled with natural light thanks to additional impact windows, creating a bright and airy interior throughout. Exceptional outdoor living awaits with two screened lanais plus a third balcony. Thoughtfully renovated, recent improvements include impact-resistant windows, a newer roof, newer HVAC system, and an on-demand tankless water heater, providing years of worry-free ownership. The finished lower level offers versatile space for a home office, fitness area, laundry room or guest accommodations, along with garage storage and a golf cart for added convenience. Offered fully furnished and turnkey, this move-in-ready residence is an outstanding full-time home, seasonal retreat, or income-producing investment with excellent rental history and opportunity for Seller Financing. Safety Harbor Club residents enjoy resort-style amenities including a heated community pool, tennis and pickleball courts, clubhouse, convenient beach access, and dockage for boating enthusiasts. Enjoy the perfect combination of updated coastal elegance, abundant indoor-outdoor living, and an unbeatable waterfront lifestyle.

4491 Escondidio Lane Unit 73, Upper Captiva

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 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 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

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

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

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

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

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

3 Beds ⋅ 2 Baths ⋅ 2026000708 MLS

The perfect boater's retreat! This charming three-bedroom waterfront home on the harbor is fully remodeled. Excellent water views from both levels. Dock permits are in place to build a dock for your dream boat. Enjoy the custom-crafted kitchen with marble countertops and stainless steel appliances, with fantastic views across the living area to the harbor. Watch the wildlife and passing boats while relaxing on the deck or screened porch. Two large guest bedrooms share a fully upgraded hall bath with a custom tile walk-in shower. The east-facing bedroom enjoys views of the harbor and another screen porch access sliding glass door, perfect for catching the fresh seaside breezes. To the west is another guest bunk room. On the second level, the spacious primary suite with dual closets & a deluxe tiled bathroom offers a huge waterfront sun porch with composite decking. Just off the primary suite is a versatile sitting room that makes a great office, media room, or extra sleeping space. Impact windows & doors, as well as a newer aluminum standing seam roof, ensure durability and peace of mind. It is just steps from community dock slips with full membership to the Safety Harbor Club amenities, pool, tennis, pickleball, and gulf beach access. This rare waterfront gem won't last. Schedule your private showing today!

4490 Harbor Bend Drive, Upper Captiva

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 Beds ⋅ 2 Baths ⋅ 2025026060 MLS

Steps from the water! You can hear the bay waters gently sloshing against the shoreline from the front deck. Enjoy beautiful bay views from the front screened-in deck and watch the boats come and go from Safety Harbor. Relax to the sounds of the cheerful sea birds that soar over Safety Harbor and watch the dolphins swim in the bay. This meticulously maintained townhouse has gorgeous views of Safety Harbor. New roof in 2023. The master suite has an updated bathroom with walk-in shower, and there is a peaceful screened-in sitting area right off the master bedroom. Two adorable bedrooms are upstairs, with sweeping bay views from one of the upstairs bedrooms. The lower area has brand new flooring, a laundry area, and full golf cart garage to park your golf cart (included). The community dockage is just steps away from the front door, with additional slips available at the community wharf where you will find a fish cleaning station and plenty of docks to fish from. Also steps away from the front door is a lovely bay beach where you can launch your kayak (included) or go fishing. Membership with Safety Harbor Club includes a community heated pool, tennis and pickle ball, private beach access, a restaurant on the water, clubhouse, and miles of pristine, uncrowded, white sugar-sand Gulf beaches. North Captiva is an island with no roads to it, so ride the bi-hourly Island Girl ferry from Pineland Marina to North Captiva and get around the island on golf carts. This unique feature of the island makes it particularly peaceful and attractive.

370 Townhouse Lane 61, Upper Captiva

2 Beds ⋅ 3 Baths ⋅ 2025018406 MLS

With Fantastic Gulf Views and a Prime Location just 350 feet from the beach, this island-style vacation retreat stands out with its extra charm and character! Located alongside North Captiva's private airstrip, which gives the home an excellent view corridor. Great for pilots and beachgoers alike! Imagine gazing at the water from your living room and sun deck, then relaxing after a day at the beach in your beautiful pool while listening to the sounds of the surf. Step inside and discover a 2-bedroom, 2.5-bath layout designed for relaxed island living. Top-level painted wood cathedral ceilings give this beachy bungalow a feeling of a much larger home, and with island flair. Abundant natural light pours in through multiple Gulf-facing French doors along the sundeck, truly bringing the outside in for sunset time! The open-concept living and dining area also features a fireplace as a focal point, while the kitchen offers modern cabinetry, solid-surface countertops, and stainless steel appliances. The primary suite includes an en-suite bath with a combined tub & shower, plus direct access to a private balcony for enjoying Gulf breezes. The guest suite is equally inviting, with its own private bath and French doors opening onto the covered screen porch. This hidden gem is a rare combination of proximity to the sugar sand beaches, poolside relaxation, and real island character at an affordable price point!

210 White Pelican Drive, Upper Captiva

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