Upper Captiva Real Estate

Upper Captiva Real Estate

Upper Captiva is a charming island city located in Lee County, Florida. Situated along the southwestern coast of the state, Upper Captiva offers a tranquil and picturesque setting for residents and visitors alike.

Known for its stunning beaches and natural beauty, Upper Captiva is a haven for outdoor enthusiasts. The island is surrounded by the sparkling waters of the Gulf of Mexico, providing ample opportunities for swimming, boating, and fishing. With its pristine white sand beaches and breathtaking sunsets, Upper Captiva is a paradise for beach lovers.

In addition to its natural attractions, Upper Captiva also boasts a close-knit community and a relaxed, laid-back atmosphere. The island is home to a small but vibrant population, making it an ideal place for those seeking a peaceful and tight-knit community.

Despite its secluded feel, Upper Captiva is conveniently located near the amenities and attractions of Lee County. Just a short boat ride away, residents can access the mainland, where they will find shopping centers, restaurants, and entertainment options.

Whether you are looking for a vacation home or a permanent residence, Upper Captiva offers a unique and idyllic lifestyle. With its pristine beaches, natural beauty, and close-knit community, this city is truly a hidden gem in the heart of Florida.

Newest Listings in 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
$170,000
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
$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
$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
$89,000
2026031238 MLS
Build your island dream home steps from the Gulf beaches on beautiful North Captiva Island! Located on a quiet circle in a higher elevation area, this desirable homesite offers an exceptional opportunity to enjoy coastal living in one of Florida's most peaceful barrier island communities. Just a short walk to beach access, you'll enjoy miles of white sand shoreline, world-class shelling, spectacular sunsets, and the relaxed island lifestyle North Captiva is known for. Resort amenities, shopping, dining, the ferry landing, and preserve trails are all just a short golf cart ride away. Imagine watching gulf views and great sunsets from your lookout, and maybe even some from your highest living floor. Whether you're planning a vacation retreat, an investment property, or your forever island home, this ideally located parcel, with potential views, provides the perfect setting to bring your vision to life.

552 Coral Circle, 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
$389,000
2026025092 MLS
Incredible Views of the Gulf from this perfectly located lot just steps to the beach! 4601 Oro Pesos Ln offers an exceptional opportunity to build your custom island dream home. Imagine sitting in your living room, looking out at the Gulf and sunsets, then walking approx. 120 feet to the beach. This generously sized 100' x 105' parcel is partially cleared and ideally positioned only two parcels back from the beach. Enjoy convenient access to beaches, preserve trails, island amenities, and the peaceful lifestyle that makes the island one of Florida's hidden coastal treasures. Opportunities to build new with this combination of proximity to the beach and water views this good are becoming increasingly rare on North Captiva, particularly at this price point!

4601 Oro Pesos Lane, Upper Captiva
$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
$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
$148,000
2026020794 MLS
A rare opportunity to own an extraordinary piece of North Captiva Island’s untouched South End coastline. This oversized parcel stretches along the island’s serene mangrove shoreline on the bay, offering a setting defined by privacy, natural beauty, and peaceful seclusion...  with incredible views of a breathtaking beach in both directions. Nestled among some of the most pristine and preserved areas of North Captiva with good water depth for a dock, this property is just steps from one of the nicest beaches in all of SW Florida, where shelling, fishing, and breathtaking sunsets become part of everyday life. This is your chance to own a meaningful piece of one of Florida’s most unique barrier islands. A place to preserve, enjoy, and hold as part of your island legacy. Whether your vision is immediate or simply for the future, properties in this naturally protected and peaceful setting are becoming increasingly rare. North Captiva Island remains one of Florida’s hidden coastal treasures—boat-access only, surrounded by preserve lands, and defined by a slower pace where nature still leads the way. Secure your piece of paradise on the South End of North Captiva, where you will be able to park your boat on one side, and enjoy the beach and sunsets on the other!

11657 Redfish Shores 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
$1,245,000
3 Beds ⋅ 2 Baths ⋅ 2026020806 MLS
541 Gulf Lane – Steps to the Sand with Sweeping Water Views & Resort-Style Outdoor Living.  This retreat offers the kind of beachside life that feels effortless from the moment you arrive. This beautifully positioned 3-bedroom, 2-bath half-duplex captures spectacular water views from every level, making the Gulf part of your everyday backdrop—from morning coffee to sunset unwinding. Designed for relaxed coastal living, this getaway features a bright, open gathering space filled with natural light and framed by views of the Gulf and sunsets. The living, kitchen, and dining zones are beautifully decorated and fully furnished. The primary suite offers a peaceful private escape, complete with a jetted soaking tub—perfect for relaxing after sun-filled beach days and evening walks along the shore. On the second level, the large guest room offers fantastic water views and a private sun deck facing the Gulf. A third guest bedroom is just around the corner, tucked into the eaves, sharing a large guest bath with a tub/shower combo. Outside is where property truly comes to life. A private pool and hot tub, expansive sun deck, and poolside bar create a resort-like setting designed for entertaining, relaxing, and making memories with family and friends. A convenient ground-level 1/2 bath and a dedicated laundry area make transitions from the beach to the pool effortless. Set along one of North Captiva's most desirable beachside lanes at a really high elevation, the home offers immediate access to the Gulf's sugar-sand shoreline, with its separate 1/2-interest in a deeded beach access lot. Whether you're seeking a personal island getaway, a vacation rental investment, or a place to gather for years to come, 541 Gulf Lane delivers the rare combination of location, views, and the laid-back luxury that defines North Captiva living. The adjacent 1/2 Duplex (543 Gulf Ln) is also available for purchase so that you can own the entire property!

541 Gulf Lane, Upper Captiva
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