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$950,000
3 Beds ⋅ 3 Baths ⋅ 2026032780 MLS ⋅ South Seas Island Resort BLDG.
SW FL has it all-- sunshine, culture, and endless recreation! From the Red Sox & Twins stadiums, beaches, boating, tours, and convenient access to an international airport, this is a perfect getaway destination. While you're enjoying everything SW FL has to offer, don't miss the chance to own a top floor, 3-bed/3-bath townhouse retreat in Bayside Villas, located within the gated South Seas Island Resort on Captiva Island. The private lanai showcases breathtaking, direct views of sunrise over the Bay, Pine Island Sound & beyond. Low green mangroves provide natural erosion protection and serve as a thriving habitat for local wildlife--beautiful, serene, and uniquely Florida. Watch boats glide in and out of the canal leading to the marina, adding a touch of coastal charm to your daily view. Take a short walk to the beach, feel the sand between your toes, and enjoy unforgettable sunsets. You're also just steps from the post office, bank, ATM, Captiva shops, and restaurants.

5321 Bayside Villas, Captiva
$735,000
2 Beds ⋅ 2 Baths ⋅ 2026030156 MLS ⋅ South Seas Island Resort BLDG.
Wake each morning to panoramic yacht harbor views and the gentle rhythm of island life from this updated waterfront retreat in Marina Villas, where Captiva's sugar-sand beaches and the sparkling Gulf of Mexico are just a short stroll away. Ideally positioned on the quiet north end of South Seas Island Resort, this furnished residence overlooks the yacht harbor and navigable channel, offering a front-row seat to passing boats, dolphins, manatees, pelicans, and unforgettable coastal sunsets. The light-filled interior features an open-concept floor plan with tile flooring throughout, a spacious kitchen with warm wood cabinetry and generous storage, plus comfortable living and dining areas that flow seamlessly to the screened lanai. The primary suite offers tranquil water views and an en-suite bath, while the guest bedroom and second full bath provide comfortable accommodations for family and friends. Surrounded by water on three sides, Marina Villas is one of Captiva's most desirable waterfront communities, offering a beautifully maintained setting, a community pool, and association boat docks available by reservation. Just a short stroll from Sunset Beach, the South Seas lagoon-style pool complex, restaurants, and the yacht harbor, this exceptional property is perfectly suited as a private island retreat, seasonal getaway, or investment opportunity where boating, beach days, and the natural beauty of Captiva are always within easy reach.

802 Marina Villas Unit 802, Captiva
$13,000,000
2026029362 MLS ⋅ Metes And Bounds BLDG.
Some places are discovered. Others are preserved. Only a select few become part of someone's legacy. Just beyond the shores of Captiva Island lies Buck Key—an extraordinary private island where untouched natural beauty, remarkable privacy, & limitless possibility converge. Opportunities of this magnitude have become exceedingly rare, making Buck Key one of the most compelling island offerings available anywhere in North America. Surrounded by the tranquil waters of Roosevelt Channel and Hurricane Hole, the island encompasses approximately 14 acres, highlighted by nearly 2,600 feet of shoreline, approximately 8.6 acres of uplands, a protected 10-acre lagoon, and a 13-foot construction-grade dock. Positioned within a remarkable 350-acre island sanctuary, Buck Key offers an unparalleled combination of seclusion and accessibility, just minutes from the restaurants, marinas, and world-renowned beaches of Captiva Island. This is not a property defined by what already exists—it is defined by what is possible. Imagine an architectural masterpiece rising above the mangroves. A private family compound passed from one generation to the next. A waterfront retreat designed entirely around your vision. Here, every sunrise arrives over protected coastal habitat, every evening concludes with Gulf sunsets, and every day offers boating, fishing, paddleboarding, kayaking, and the quiet luxury of complete privacy. In an era when waterfront land grows increasingly scarce and entitlement opportunities continue to diminish, Buck Key represents something that can no longer be replicated. It is a place where conservation and luxury coexist, where nature becomes the ultimate amenity, and where the opportunity to create something entirely bespoke remains remarkably intact. Legacy properties are seldom created. They are preserved, stewarded, and ultimately entrusted to those with the vision to recognize their significance. Buck Key is more than an island. It is an invitation to create something that will endure for generations.

Buck Key, Captiva
$1,295,000
3 Beds ⋅ 2.5 Baths ⋅ 2026029152 MLS ⋅ Captiva Shores Condo BLDG.
Opportunity is Knocking! If you are looking for a beautiful Gulf to Bay property to call home on Captiva's premier Tween Waters stretch you've found it! This ideal location offers miles of shell strewn beach, unparalleled sunsets, deep water direct access boating with dockage, pool and weekly rentals. This particular unit features beautiful bay views and an open floor plan with a large lanai. The guest rooms are located on the main level with the primary suite encompassing the top level. Available for the first time & owned by the same family for over 40 years. The complex is wrapping up construction and is near completion. The unit will be brought back to a white box with the drywall completed. This is a fabulous opportunity to select your finishes and reinvent this beauty with new interior finishes. A short stroll away is Captiva Village with its shopping and dining opportunities. Watch the sunrise from your balcony and brilliant sunsets from the beach. Projected Gross Revenue 2025 $143,718; 2026 $148,029.

15411 Captiva Dr Unit 3B, Captiva
$6,995,000
6 Beds ⋅ 4.5 Baths ⋅ 2026023434 MLS ⋅ Metes And Bounds BLDG.
At the southernmost tip of Captiva Island, where the turquoise waters of the Gulf meet the tranquil expanse of Pine Island Sound, lies one of Southwest Florida’s extraordinary residential offerings. Encompassing more than an acre stretching seamlessly from Gulf to Bay, this private estate commands an exceptionally rare setting immersed in water, light and natural beauty from every direction. Beyond the gated entrance, a dramatic composition of architecture and landscape unfolds. A resort-style pool and spa, lush tropical grounds, and a private dock with boat lift create a lifestyle defined by effortless access to the open Gulf and protected waters of the bay. Few properties can claim such a remarkable dual-waterfront existence. Designed to celebrate its surroundings, the residence is a masterful blend of warmth, craftsmanship and connection to nature. Stunning flooring, beamed ceilings, and thoughtfully curated finishes create an atmosphere that is sophisticated and inviting. Expansive walls of impact-rated glass frame panoramic vistas at every turn, transforming the ever-changing interplay of sea, sky and light into living works of art. The grand living room serves as the heart of the home, anchored by a striking fireplace and framed by breathtaking waterfront panoramas. To the west, endless views of sugar white beaches, the shimmering Gulf and Captiva’s legendary sunsets unfold. To the east, Pine Island Sound, mangrove islands and dramatic coastal skies create an equally captivating backdrop. The kitchen blends timeless charm with modern functionality, featuring exceptional millwork, premium appliances and a unique wood-burning fireplace that lends an unexpected touch of character. Flowing seamlessly to the bayfront lanai, it invites leisurely mornings overlooking the water and unforgettable evenings gathered around the firepit beneath the stars. The primary suite is a retreat unlike any other. A central fireplace separates intimate living spaces connected by rich wood flooring designed to embrace the estate’s dual-waterfront setting. One side opens to a private balcony overlooking the Gulf, while the other captures mesmerizing bay views through a tranquil window seat. The spa-inspired bath has been beautifully updated and offers the rare luxury of spectacular water views. Serviced by a private elevator connecting all levels, each guest suite enjoys its unique perspective of the surrounding coastal landscape. Outside, a private dock extends into the bay, providing immediate access to world-class boating, fishing and island exploration, while a private path leads directly to Captiva’s famed beaches. A rare offering, this estate represents the pinnacle of island living, a place where architecture and nature exist in harmony, and where every sunrise and sunset unfolds over water. Rarely does a property capture the essence of Captiva so completely.

17201 Captiva Dr, Captiva
$199,000
2026004719 MLS ⋅ Upper Captiva Shores BLDG.
You are looking to build your new getaway, but how do you get away from it all? A true barrier island with no bridges. Separate yourself from the world and enjoy the peace and quiet. It’s just you, your companions and the beach on North Captiva Island. Only accessible by boat or plane, this bay to beach lot offers expansive views of the Gulf of Mexico. The closely neighboring barrier island Sanibel is a popular tourist destination known for its unique shelling and beaches (due to the east/west orientation) and wildlife refuges. There are only a handful of bay to beach lots that are buildable on North Captiva Island. Build your sanctuary on one of the best rated beaches in Florida. Owner financing may be available, call for terms!!

12541 South Banks Dr, Captiva
$875,000
3 Beds ⋅ 3 Baths ⋅ 2026017261 MLS ⋅ South Seas Island Resort BLDG.
Highly sought-after, updated 3 bed, 3 bath two-story villa stands apart with rare features not found in other Bayside units, overlooking the tranquil waters of Pine Island Sound, where unchanging estuary views and native wildlife create a peaceful, elevated backdrop—just moments from the best of Captiva Island. Rare features of this top-floor unit include a walk-in pantry—an uncommon luxury in Bayside 3-bedroom villas—all-new hurricane-impact windows and sliders, and a residence that has been gently used as a private second home and never enrolled in a rental program—an added advantage in condition and care. Whether enjoyed as a private island retreat or leveraged as a high-performing investment, this residence offers rare flexibility within a renter-friendly community and stands as one of the least expensive 3-bedroom opportunities on Captiva. The interior is anchored by an updated kitchen with quartz countertops, glass-front upper cabinetry, and matching appliances, flowing seamlessly into the main living area. Three generously sized bedrooms and three full baths include two primary suites—one on the main level and one upstairs—each with its own ensuite, offering ideal separation for guests or extended stays. A third guest bedroom also enjoys a private bath, while an in-unit washer and dryer adds everyday convenience. The screened lanai feels like your own private perch above Pine Island Sound, where it’s just you, the water, and the rhythm of nature. From both the kitchen and lanai, morning sunrises unfold over the Sound, setting the tone for slow mornings, passing wildlife, and uninterrupted calm. Set within South Seas Island Resort in the desirable Bayside Villas enclave, just a stone’s throw from the sugar-white Gulf beaches, the Village of Captiva, and Captiva Landing. Residents and guests enjoy a bayside pool and spa with generous lounging areas, along with under-building parking for added ease. Where time slows, views remain untouched, and every return feels like coming home—this is Captiva at its finest.

5323 Bayside Villas Unit 24, Captiva
$4,890,000
3 Beds ⋅ 3 Baths ⋅ 2026010812 MLS ⋅ Captiva BLDG.
Wake up to this every day... Captiva's Best Value for Buyers Seeking Walkability, Deep-Water Boating, and the Authentic Island Lifestyle. Imagine beginning each morning with coffee overlooking the sparkling waters of Pine Island Sound as dolphins glide past your private dock and pelicans soar overhead. This is more than a waterfront home, it's a lifestyle that few properties can offer. Perfectly positioned in the heart of Captiva Village, this exceptional bayfront residence combines expansive, unobstructed water views, direct Gulf boating access, and one of the island's most walkable locations. Leave the car behind and stroll to Captiva's renowned restaurants, charming boutiques, Captiva Chapel by the Sea, the library, local galleries, and the sugar-sand beaches of the Gulf of Mexico. Few waterfront homes offer the rare opportunity to enjoy both a premier boating lifestyle and the convenience of village living. Set on nearly one-half acre, the property features a private deep-water dock with no bridges to the Gulf, making it an ideal retreat for boating enthusiasts, anglers, and those who simply love life on the water. Designed to capture the timeless charm of Old Florida, the home offers warm, inviting living spaces where family and friends naturally gather. Spend the day boating to nearby islands, relaxing by the pool, fishing from your dock, or simply watching the ever-changing beauty of Pine Island Sound unfold before you. Evenings are reserved for spectacular sunsets, waterfront dining just a short walk away, and the relaxed pace that has made Captiva one of Florida's most treasured destinations. Adding to its appeal, the home has enjoyed a successful vacation rental history, providing an exceptional opportunity for buyers seeking both a luxury retreat and income-producing potential. Whether you're searching for a full-time residence, seasonal escape, or legacy waterfront property, 15153 Captiva Drive represents one of Captiva's most compelling values. Offering an irreplaceable combination of walkability, direct boating access, breathtaking bay views, and authentic island charm, this is the Captiva lifestyle you've been dreaming about!

15153 Captiva Dr, Captiva
$549,000
1 Beds ⋅ 2 Baths ⋅ 2026002394 MLS ⋅ South Seas Island Resort BLDG.
Just renovated Bayside Villa located in the gated private South Seas Resort. New kitchen and bathrooms to include granite countertops, shaker cabinets, new flooring, gorgeous walk-in shower all set in a soothing sea salt palette. Wake up to sunrise over Pine Island Sound. The Bayside amenities include an oversized sun-drenched pool and spa, under building parking, on site laundry, pool baths, marina side grills and picnic areas. No rental commitments so all options open. Move in and enjoy or place your property in a rental program. Just footsteps to the beach for a dip in the Gulf of Mexico. Easy access to village of Captiva's shops, restaurants, boating and water sports. Enjoy South Seas world class amenities with membership. Immerse yourself in the luxury of this stunning property. This exclusive opportunity enhances your living experience, offering a range of premium amenities and services tailored for members and guests. With this exceptional membership, enjoy unparalleled access to facilities that elevate your lifestyle.

5122 Bayside Villas, Captiva
$489,000
1 Beds ⋅ 2 Baths ⋅ 2025024926 MLS ⋅ South Seas Island Resort BLDG.
This beautifully appointed one-bedroom, two-bathroom villa at Bayside Villas is not only a stunning coastal retreat but also a fantastic investment property with daily rental capabilities. Offering breathtaking views of the marina and bay, leading to open waters, this villa features luxurious wood-like tile flooring, granite countertops, and coastal-inspired decor throughout. Nestled in the heart of the Bayside Villas community, residents enjoy convenient access to Captiva's pristine beaches, vibrant village, and unforgettable sunsets. Community amenities include a pool, spa, under-building parking, and an assigned storage locker. Whether for personal enjoyment or investment purposes, this property is sure to delight. Your slice of paradise awaits!

4216 Bayside Villas, Captiva
$494,900
1 Beds ⋅ 2 Baths ⋅ 2025017415 MLS ⋅ South Seas Island Resort BLDG.
Start each day surrounded by the sights and sounds of island life from this second-floor, one-bedroom, two-bath furnished condo overlooking Pine Island Sound. Sunlight pours through wide sliders that open to a private lanai, where gentle breezes carry the scent of salt air and the call of seabirds. Watch dolphins play and boats drift by—a constant reminder you’re living on island time. Located within the southern enclave of South Seas Resort blends comfort and convenience with an easygoing Captiva lifestyle. Tile flooring throughout creates a cool, carefree atmosphere, while the kitchen features stainless-steel appliances and open sightlines to the bay. The guest bath provides added flexibility for visitors, and the bedroom offers a peaceful retreat after a day in the sun. Owners participating in the Resort Rental Program and Club Captiva enjoy access to full resort amenities, including Sunset Beach, pools, lounges, umbrellas, and chairs for relaxed days along the Gulf—all just a short stroll away. A ground-level storage locker in the 5000 building is perfect for keeping beach gear, SUP, or fishing gear! From this ideal location, it’s easy to enjoy all that Captiva has to offer—bike along palm-lined roads, kayaking through mangroves, or watching the sunset over the Gulf. Explore the island by golf cart, or unwind with cocktails as the sun dips below the horizon. The Bayside Villas community also features a waterfront pool, spa, and under-building parking. 5232 Bayside Villas offers a front-row seat to Captiva’s natural beauty and a laid-back rhythm that makes every day feel like vacation.

5232 Bayside Villas, Captiva
$445,000
1 Beds ⋅ 2 Baths ⋅ 2025012075 MLS ⋅ South Seas Island Resort BLDG.
At 5132 Bayside Villas, each day is written in light, water, and breeze. Dawn begins on the lanai, where Pine Island Sound awakens with color—sunrise glows across the horizon, pelicans skim the waves, and fishing boats slip toward open water. The bay becomes your backdrop, alive with sails, seabirds, and the shifting palette of the sky. The villa itself balances coastal charm with modern ease. A 1BD/2BA first-floor retreat, it offers granite counters, stainless appliances, crisp cabinetry, wide-plank tile flooring, and crown molding. The living spaces flow naturally to the lanai, where the outdoors remains the centerpiece. The primary suite offers a calm retreat, while a second bath mirrors the same fresh finishes. Yet what makes this villa extraordinary is not just the design—it’s the rhythm of Captiva life outside its doors. Within minutes, you can sink your feet into the Gulf sands, celebrated for their shells and sunlit shallows. Island pathways invite golf cart rides and bike cruises into Captiva Village, where the hum of music, dining, and laughter sets a different tempo. Afternoons bring choices: a swim in the bayside pool, a paddle through calm waters where dolphins are frequent companions, or a wander through palm-lined trails. As the day winds down, the stage shifts once more. Perhaps you’ll gather with neighbors for cocktails while the boats return across the channel or cross the island to witness sunset blaze into the Gulf. And when evening deepens, stars scatter above the mangroves, promising another sunrise to come. With amenities like under-building parking, private storage, and a bayside pool and spa, 5132 Bayside Villas offers not just a home but an island way of life—measured in sunrises, sails, and timeless Captiva moments.

5132 Bayside Villas, Captiva
$4,800,000
3 Beds ⋅ 3 Baths ⋅ 225029219 MLS ⋅ Metes And Bounds BLDG.
Nestled along the most coveted stretch of Captiva Island’s Gold Coast, This charming Old Florida-style main house boasts a private pool area and expansive deck space, creating a perfect retreat. Inside, high vaulted ceilings and an open kitchen enhance the spacious feel. Situated in the Estate Zone District, this property offers deeded beach access just steps away. Perfectly positioned in the heart of this prestigious area, the dune-wide beachfront setting offers breathtaking views and unparalleled serenity.Whether you choose to enjoy it as is or expand with additional square footage or a separate living structure, the possibilities for creating a private family compound are endless. A cherished part of a family estate for over 40 years, this property is surrounded by lush tropical landscaping, enhancing its secluded and tranquil ambiance. For those seeking the ultimate private retreat, two adjacent properties—16530 Captiva Drive and 16548 Captiva Drive—are also available, presenting a rare opportunity to create a 300-foot beachfront and 100-foot bayfront compound spanning over 5.25 acres. Whether enjoyed as a standalone sanctuary or as part of a grand waterfront estate, this is truly a once-in-a-lifetime chance to own an iconic piece of Captiva Island.

16543 Captiva Dr, Captiva
$5,250,000
4 Beds ⋅ 3 Baths ⋅ 225013345 MLS ⋅ Dickeys John R Subd BLDG.
Nestled between the Gulf and Bay, this stunning beachfront home offers unparalleled 180-degree views of both pristine waters, coupled with direct deep-water boating access and a private dock space with lift. Perfect for those who enjoy both the beach and boating lifestyle, this residence seamlessly blends luxurious indoor spaces with expansive outdoor living areas. The thoughtfully designed split floor plan provides ultimate privacy for owners and guests, while the open-concept gathering areas flow effortlessly from room to room. Sunlight pours through large windows, highlighting the voluminous interiors and enhancing the beauty of the home. The light-filled spaces lead to multiple outdoor areas ideal for entertaining or relaxing, all while taking in the spectacular views. Enjoy easy maintenance witha galvalume roof, composite decking, aluminum railings, durable stucco finish, impact windows and doors and more. The beautifully landscaped property boasts a large fenced backyard with pavers, perfect for hosting or enjoying the outdoors, plus a spacious pool and spa for ultimate relaxation. The gourmet kitchen offers fantastic views of the Gulf, stone countertops, a large pantry, a cozy dining area, and an adjacent deck for alfresco dining. The master suite is a true retreat, featuring incredible Gulf views, a spacious bath, two walk-in closets, and a private office. With a 3-car garage, this home is as practical as it is luxurious—making it the perfect waterfront getaway. NOTE, this property is atsome of the highest elevation in the X Zone of Captiva Island.

15899 Captiva Dr, Captiva
$12,000,000
225009365 MLS ⋅ Dickeys John R Subd BLDG.
One of the Best waterfront properties on the West Coast of Florida. Gulf to Bay, Sunrise to Sunset, 125 feet of Incredible Water Frontage on the Tween Waters stretch on Captlva Island, Florida. Build your Masterpiece here located at One of the highest point elevations on Captlva Island. Located at the mouth of the Bay & Roosevelt Channel. This property enjoys Deep Water Yacht Access & One of the Best covered boat house, lift & dock set ups you will find. In addition to the lot, a full set of the Masterful Work of Art fully completed blue prints by Nationally known Architect John Cooney of Naples (of what could be built) are available for purchase. This property Is a One of A Kind!

15819 Captiva Dr, Captiva
$9,450,000
6 Beds ⋅ 6.5 Baths ⋅ 224082961 MLS ⋅ Metes And Bounds BLDG.
A one of a kind offering with 150ft of water frontage laden with rich national history. President Theodore Roosevelt began frequenting Captiva in 1908. In 1917 he staged his houseboat at this very location for his legendary Devil Fish expedition of which he hunted and gathered for the Smithsonian. In the 1930s this property served as one of only two locations to deliver goods to Captiva mainly of which was building materials, delivered by barge. The oversized grandfathered dock was built in 1939 by the WPA which was founded by Franklin Roosevelt. The romantic boathouse, which is cantilevered over the water and is also grandfathered in, was constructed in 1953 by Harold Bixby. Bixby was one of Charles Lindbergh's primary backers in 1927 when Lindbergh accomplished his transatlantic flight in The Spirit of St Louis. The boathouse with two bedrooms and caretaker cottage with one bedroom stand today in superb condition with a recently installed composite roof with a 100 year life expectancy. As you approach the main house, you are greeted with the charm of olde world Southern architecture. Inside you will find soaring ceilings of cypress, and beautiful views of Roosevelt Channel along with three spacious bedrooms, a library and an office. Resting on over 1.3 acres with deeded beach access.

16777 Captiva Dr, Captiva
$1,375,000
2 Beds ⋅ 2 Baths ⋅ 225011517 MLS ⋅ Captiva Hide-A-Way Condo BLDG.
Spectacular, direct Bayfront vistas from this furnished, 2 bedroom and 2 bath condo situated in Captiva's "Village" at Captiva Hide-A-Way. “Boater’s Paradise” - dock your boat right out your back door for easy access to Pine Island Sound and the Gulf. Experience magical sun and moon rises from your private lanai and stunning sunsets from the Gulf beach. Conveniently located close to the marina for all your boating needs. Enjoy some of the BEST fishing on the West coast of Florida! Amenities include a private dock with a RARE opportunity to add your own boat lift, fishing pier, sparkling pool, and BBQ grill. All this just a short 5 minute stroll from the Gulf where you’ll enjoy incredible sugar sand beaches and some of the world's best shelling. Walk into the heart of Captiva's "Village" for dining, shopping, entertainment, marina and more. The building has been totally renovated post hurricane with new roof, siding, windows and lanais. Condo offers tile plank floors throughout main living area and carpet in bedrooms, new air conditioner handler/compressor and tankless water heater. New custom tile and exotic stone and marble vanity in both bathrooms. Stainless steel appliances, granite counters in kitchen and built-in buffet. Owners can have two pets, under 30lbs.

11400 Old Lodge Ln Unit 1C, Captiva
$1,499,000
2 Beds ⋅ 2 Baths ⋅ 224020201 MLS ⋅ Sunset Captiva Condo BLDG.
Sunset Captiva Harbor Side offers a rare chance to own in one of Captiva’s most unique Gulf-to-Bay communities, perfectly situated in the heart of historic Captiva Village. This coveted location blends exceptional value with sweeping views of Pine Island Sound, Buck Key, and abundant island wildlife. As the only community in the Village offering full amenities, Sunset Captiva delivers an unmatched island lifestyle. This newly remodeled residence features luxury finishes throughout, with two spacious bedrooms and open, airy living areas designed for effortless coastal living. Highlights include deep-water dockage, a community pool, tennis and pickleball, elevator access, and a private boardwalk leading directly to the Gulf. The boutique 10-unit complex also provides a ground-floor storage area large enough for a golf cart—an island essential. Offered fully furnished and turnkey, this property is ideal as a private retreat, income-producing rental, or smart investment. With its prime location, elevated design, and resort-style amenities, Sunset Captiva Harbor Side is your opportunity to claim a true piece of paradise.

15123 Captiva Dr Unit 103, Captiva