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$1,550,000
3Beds
3Baths
2,300Sqft
Captiva, Florida, 33924, United States
Situated at the northernmost tip of Captiva Island is Lands End. Appropriately named, this intimate complex provides a setting like no other with a 180 degrees vistas from The Gulf of Mexico across the stunning golf course to Pine Island Sound. This penthouse is beautifully updated and spacious with 2300 ft.2 of living area along with two commodious sundecks and parking under the building.
Homes and Land
$1,550,000
1666 Lands End Village
3Beds
3Baths
2,300Sqft
Captiva, Florida, 33924, United States
Situated at the northernmost tip of Captiva Island is Lands End. Appropriately named, this intimate complex provides a setting like no other with a 180 degrees vistas from The Gulf of Mexico across the stunning golf course to Pine Island Sound. This penthouse is beautifully updated and spacious with 2300 ft.2 of living area along with two commodious sundecks and parking under the building. The floor plan is gracious and flows beautifully with all areas. Offering a gorgeous pool area and soon-to-be lushly landscaped grounds along with a private fitness center and access to the beach, Lands End is your own resort. Pro Forma Attached. Projection Gross income for 2026 is 213,000. This property in not encumbered by any program whatsoever so a future owner can do as they see fit.
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Homes and Land
$1,550,000
1666 Lands End Village
3Beds
3Baths
2,300Sqft
$1,550,000
Captiva, Florida, 33924, United States
$9,450,000
6Beds
6.5Baths
5,346Sqft
Captiva, Florida, 33924, United States
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.
Homes and Land
$9,450,000
16777 Captiva Drive
6Beds
6.5Baths
5,346Sqft
Captiva, Florida, 33924, United States
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 Lindberghs 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.
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Homes and Land
$9,450,000
16777 Captiva Drive
6Beds
6.5Baths
5,346Sqft
$9,450,000
Captiva, Florida, 33924, United States
$3,500,000
3Beds
3.5Baths
3,028Sqft
Captiva, Florida, 33924, United States
Discover the ultimate Artist retreat with this exceptional 1.4-acre bay front estate parcel on Captivas coveted Roosevelt Channel. Nestled among lush, mature vegetation, this property offers breathtaking waterfront views, abundant wildlife, and a private dock with direct access to the Intracoastal Waterway and Gulf of Mexico.
Homes and Land
$3,500,000
16891 Captiva Drive
3Beds
3.5Baths
3,028Sqft
Captiva, Florida, 33924, United States
Discover the ultimate Artist retreat with this exceptional 1.4-acre bay front estate parcel on Captivas coveted Roosevelt Channel. Nestled among lush, mature vegetation, this property offers breathtaking waterfront views, abundant wildlife, and a private dock with direct access to the Intracoastal Waterway and Gulf of Mexico. Your Picturesque estate also offers a deeded beach access through a scenic walkway to the Gulf of Mexico across Captiva Drive. Main Residence: - Fully remodeled 3-bedroom, 3-bath home - Impact glass windows & metal roof for modern safety & efficiency - Private pool & spa for island-style relaxation - Charming coastal-inspired interiors with elegant finishes Art Studio & Guest Retreat: - Distinctive architectural design - Second-level space with potential for future expansion - A tranquil creative space or additional guest quarters Surrounded by nature, this estate offers a serene sanctuary where you can experience manatees, dolphins, and incredible birdlife right in your backyard. A rare opportunity to embrace the Captiva Island lifestyle with privacy, charm, and endless waterfront adventures. Ground level home that did not flood in any of the recent storms........Schedule your private showing today!
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Homes and Land
$3,500,000
16891 Captiva Drive
3Beds
3.5Baths
3,028Sqft
$3,500,000
Captiva, Florida, 33924, United States
$1,499,000
2Beds
2Baths
1,323Sqft
Captiva, Florida, 33924, United States
Sunset Captiva Harbor Side offers a rare chance to own in one of Captivas 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.
Homes and Land
$1,499,000
15123 Captiva Drive unit: 103
2Beds
2Baths
1,323Sqft
Captiva, Florida, 33924, United States
Sunset Captiva Harbor Side offers a rare chance to own in one of Captivas 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.
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Homes and Land
$1,499,000
15123 Captiva Drive unit: 103
2Beds
2Baths
1,323Sqft
$1,499,000
Captiva, Florida, 33924, United States
$11,500,000
6Beds
7.1Baths
6,292Sqft
Captiva, Florida, 33924, United States
Experience inspired luxury and unmatched rental potential at Shell Seekers, a one-of-a-kind Captiva Island beach estate. Shell Seekers enjoys an enviable position on Captiva Drive, offering both privacy and easy access to the islands renowned restaurants, shopping, and recreational activities.
Michael Polly
$11,500,000
17030 Captiva Drive
6Beds
7.1Baths
6,292Sqft
Captiva, Florida, 33924, United States
Experience inspired luxury and unmatched rental potential at Shell Seekers, a one-of-a-kind Captiva Island beach estate. Shell Seekers enjoys an enviable position on Captiva Drive, offering both privacy and easy access to the islands renowned restaurants, shopping, and recreational activities. The propertys Gulf-front location ensures permanent unobstructed water views and direct beach access – a rarity that becomes more precious each year. This 6-bedroom, 7.5-bath masterpiece embraces Olde Florida architecture with modern comforts. Expansive screened and open porches invite seamless indoor-outdoor living, ideal for elegant entertaining or quiet evenings as the sun sets over the jeweled-toned waters of the Gulf. Step inside to soaring two-story coffered ceilings, a dramatic great room, and a gourmet kitchen designed for hosting at scale. Finishes include crown molding, hardwood floors, coastal-inspired décor, and multiple gathering spaces tailored for multi-generational living. The private top-floor primary suite features a fireplace, sitting area, and sweeping Gulf vistas. With an elevator, guest suites, a loft, and a flexible floor plan, this residence adapts effortlessly to families and guests alike. The outdoor living spaces are equally impressive, featuring a heated pool and spa, expansive decking, and direct access to Captivas pristine Gulf beaches. Multiple covered and open terraces provide the perfect setting to enjoy spectacular sunsets and the islands legendary shelling opportunities right at your doorstep. Hardie board siding, impact-rated windows, and a whole-home generator provide beauty, function, and peace of mind. A rare opportunity to own one of Captivas most iconic Gulf-front properties—whether as a private retreat, a showpiece for entertaining, or a legacy investment with proven returns. New roof, new A/C, new flooring, new appliances - completely remodeled like new.
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Michael Polly
$11,500,000
17030 Captiva Drive
6Beds
7.1Baths
6,292Sqft
$11,500,000
Captiva, Florida, 33924, United States
$11,500,000
7Beds
0.1Baths
15,086Sqft
Captiva, Florida, 33924, United States
Experience inspired luxury and unmatched rental potential at Shell Seekers, a one-of-a-kind Captiva Island beach estate. Shell Seekers enjoys an enviable position on Captiva Drive, offering both privacy and easy access to the islands renowned restaurants, shopping, and recreational activities.
Michael Polly
$11,500,000
17030 Captiva Dr
7Beds
0.1Baths
15,086Sqft
Captiva, Florida, 33924, United States
Experience inspired luxury and unmatched rental potential at Shell Seekers, a one-of-a-kind Captiva Island beach estate. Shell Seekers enjoys an enviable position on Captiva Drive, offering both privacy and easy access to the islands renowned restaurants, shopping, and recreational activities. The propertys Gulf-front location ensures permanent unobstructed water views and direct beach access – a rarity that becomes more precious each year. This 6-bedroom, 7.5-bath masterpiece embraces Olde Florida architecture with modern comforts. Expansive screened and open porches invite seamless indoor-outdoor living, ideal for elegant entertaining or quiet evenings as the sun sets over the jeweled-toned waters of the Gulf. Step inside to soaring two-story coffered ceilings, a dramatic great room, and a gourmet kitchen designed for hosting at scale. Finishes include crown molding, hardwood floors, coastal-inspired décor, and multiple gathering spaces tailored for multi-generational living. The private top-floor primary suite features a fireplace, sitting area, and sweeping Gulf vistas. With an elevator, guest suites, a loft, and a flexible floor plan, this residence adapts effortlessly to families and guests alike. The outdoor living spaces are equally impressive, featuring a heated pool and spa, expansive decking, and direct access to Captivas pristine Gulf beaches. Multiple covered and open terraces provide the perfect setting to enjoy spectacular sunsets and the islands legendary shelling opportunities right at your doorstep. Hardie board siding, impact-rated windows, and a whole-home generator provide beauty, function, and peace of mind. A rare opportunity to own one of Captivas most iconic Gulf-front properties—whether as a private retreat, a showpiece for entertaining, or a legacy investment with proven returns. New roof, new A/C, new flooring, new appliances - completely remodeled like new.
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Michael Polly
$11,500,000
17030 Captiva Dr
7Beds
0.1Baths
15,086Sqft
$11,500,000
Captiva, Florida, 33924, United States
$11,900,000
5Beds
5.5Baths
5,751Sqft
Captiva, Florida, 33924, United States
Set amidst the glistening waters of the Gulf and the captivating Bay, this stunning estate epitomizes unparalleled luxury and exclusive waterfront living. Stretching from beachside to bayside, the property offers dazzling sunrises & sunsets, and shows meticulous renovations and upgrades throughout, with no detail overlooked.
Homes and Land
$11,900,000
15735 /737 Captiva Drive
5Beds
5.5Baths
5,751Sqft
Captiva, Florida, 33924, United States
Set amidst the glistening waters of the Gulf and the captivating Bay, this stunning estate epitomizes unparalleled luxury and exclusive waterfront living. Stretching from beachside to bayside, the property offers dazzling sunrises & sunsets, and shows meticulous renovations and upgrades throughout, with no detail overlooked. Every aspect of this magnificent estate has been crafted with the utmost care and precision, ensuring a truly exceptional living experience. The main residence is a stunning blend of elegance and comfort, highlighting airy living spaces and breathtaking panoramic views of the Gulf and Bay. The home features shell stone floors, custom designs, exquisite finishes, advanced technology, a new whole home generator, elevator to all floors, and refined amenities. The chefs kitchen, equipped with the finest of Viking appliances, is sure to inspire culinary creativity. The impressive indoor and outdoor entertaining areas seamlessly connect via pocketing sliders, creating a harmonious flow between spaces. The expansive outdoor area is framed by a sparkling pool and spa, artfully designed with grace and sophistication in mind. From the immaculate garage to the private, luxurious top-floor guest suites, the numerous comfort features elevate and enhance island living. A special aspect of this iconic estate is the historic boathouse where Teddy Roosevelt stayed in 1917, expertly curated as a charming & updated guest cottage with timeless character, and breathtaking bay views. A kayak launch and copious Trex deck extending into the bay and culminating in a new covered boat lift complete the picture of this coastal castle by the sea. Dolphins Crossing presents a rare opportunity to own one of the very few properties that encompasses both Gulf and Bay, offering the ultimate Captiva Island lifestyle. Truly the best of both worlds, owning a piece of history while enjoying the finest in modern luxury living. This is more than just a home - it is a statement legacy.
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Homes and Land
$11,900,000
15735 /737 Captiva Drive
5Beds
5.5Baths
5,751Sqft
$11,900,000
Captiva, Florida, 33924, United States
$3,995,000
4Beds
3.5Baths
2,980Sqft
Captiva, Florida, 33924, United States
Enjoy breathtaking sunsets over the Gulf of Mexico from this inviting beach cottage, perfectly situated within walking distance of Captiva Village. Featuring open-beam ceilings, a gracious living area, and multiple decks that capture stunning views, this home radiates island charm and comfort.
Homes and Land
$3,995,000
15301 Captiva Drive
4Beds
3.5Baths
2,980Sqft
Captiva, Florida, 33924, United States
Enjoy breathtaking sunsets over the Gulf of Mexico from this inviting beach cottage, perfectly situated within walking distance of Captiva Village. Featuring open-beam ceilings, a gracious living area, and multiple decks that capture stunning views, this home radiates island charm and comfort. The spacious kitchen and open floor plan make entertaining effortless, while the top-floor primary suite offers sweeping water vistas and a serene retreat. Outside, a beautiful pool area with generous decking provides the ideal space for sunbathing or gatherings under the stars. Not currently part of a rental program, this property holds excellent potential for strong rental performance. Projected Gross Income provided by Kingfisher Vacations: 416,500.00 (2026); 428,995.00 (2027); 441,864.85 (2028); 455,120.80 (2029); 468,774.42 (2030); 482,837.65 (2031) Located in Captivas golf cart zone, this quintessential island home offers the perfect blend of relaxation, convenience, and Gulf-front beauty.
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Homes and Land
$3,995,000
15301 Captiva Drive
4Beds
3.5Baths
2,980Sqft
$3,995,000
Captiva, Florida, 33924, United States
$6,500,000
1.06Sqft
Captiva, Florida, 33924, United States
Situated along the most coveted stretch of Captiva Island’s Gold Coast, this 100-foot beachfront lot presents a rare opportunity to start fresh on one of the most iconic shorelines in Southwest Florida.
Michael Polly
$6,500,000
16548 Captiva Dr
1.06Sqft
Captiva, Florida, 33924, United States
Situated along the most coveted stretch of Captiva Island’s Gold Coast, this 100-foot beachfront lot presents a rare opportunity to start fresh on one of the most iconic shorelines in Southwest Florida. Recently cleared, the property is ready for your vision, whether that means designing a custom beachfront retreat from the ground up or creating something truly extraordinary by combining it with the adjacent 200-foot beachfront parcel and the 100-foot bayfront property across the street. Together, these offerings present the potential for a one-of-a-kind waterfront compound spanning over 5.25 acres with 300 feet on the Gulf of Mexico and 100 feet on the Bay. Cherished as part of a family estate for over 40 years, this location offers dune-wide beachfront, sweeping views, and a level of privacy and serenity that is unmatched. Whether built as a standalone sanctuary or envisioned as part of a grand, multi-property estate, this is a once-in-a-lifetime opportunity to create your own legacy on Captiva Island.
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Michael Polly
$6,500,000
Captiva, Florida, 33924, United States
Situated along the most coveted stretch of Captiva Island’s Gold Coast, this 100-foot beachfront lot presents a rare opportunity to start fresh on one of the most iconic shorelines in Southwest Florida.
Michael Polly
$6,500,000
16548 Captiva Drive
Captiva, Florida, 33924, United States
Situated along the most coveted stretch of Captiva Island’s Gold Coast, this 100-foot beachfront lot presents a rare opportunity to start fresh on one of the most iconic shorelines in Southwest Florida. Recently cleared, the property is ready for your vision, whether that means designing a custom beachfront retreat from the ground up or creating something truly extraordinary by combining it with the adjacent 200-foot beachfront parcel and the 100-foot bayfront property across the street. Together, these offerings present the potential for a one-of-a-kind waterfront compound spanning over 5.25 acres with 300 feet on the Gulf of Mexico and 100 feet on the Bay. Cherished as part of a family estate for over 40 years, this location offers dune-wide beachfront, sweeping views, and a level of privacy and serenity that is unmatched. Whether built as a standalone sanctuary or envisioned as part of a grand, multi-property estate, this is a once-in-a-lifetime opportunity to create your own legacy on Captiva Island.
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Michael Polly
$9,450,000
3Beds
3.1Baths
3,152Sqft
Captiva, Florida, 33924, United States
Rare opportunity to purchase a luxurious Gulf Front Estate on Captiva Island within the gated resort community of South Seas. This stunning, coastal 5 bdrm property offers 102 of beach frontage w/ breathtaking sunsets and views of the gulf. Totally renovated and remodeled with new quality craftsmanship and attention to every detail.
Michael Polly
$9,450,000
941 South Seas Plantation Road
3Beds
3.1Baths
3,152Sqft
Captiva, Florida, 33924, United States
Rare opportunity to purchase a luxurious Gulf Front Estate on Captiva Island within the gated resort community of South Seas. This stunning, coastal 5 bdrm property offers 102 of beach frontage w/ breathtaking sunsets and views of the gulf. Totally renovated and remodeled with new quality craftsmanship and attention to every detail. All new interior furnishings and amenities include, striking quartzite countertops and custom solid wood cabinetry in the kitchen, coffee bar & primary bathroom, beautiful wide plank wood floor throughout, custom ceiling details, private elevator, laundry w/ lots of storage, powder bath, electric blinds and designer furnishings. The spacious kitchen features a gas Wolf range, beverage cooler, refrigerator, freezer, microwave and dishwasher. Gorgeious views of the beach from the kitchen, dining & great room. The penthouse style primary bedroom features a sitting area, laundry, beautiful bathroom and private deck over look the beach which is perfect for enjoying a morning cup of coffee or evening star gazing with a tropical beverage. Multiple sets of sliders lead to a huge outdoor deck featuring an elevated swimming pool. The structure has concrete pilings, a new standing seam metal roof, impact glass throughout, expansive circular driveway with pavers, tropical landscaping with pops of color and strategically designed low voltage lighting. There is an oversized 2 car garage with room for bikes, beach & fishing gear, a separate golf cart garage, and an epoxy finish on the floor. The bonus area (non-conforming) is fun for guests and a nice addition to the home. After sun and fun, enjoy the refreshing outdoor shower for a quick rinse before splashing in the pool. This home has it all location and lifestyle.
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Michael Polly
$9,450,000
941 South Seas Plantation Road
3Beds
3.1Baths
3,152Sqft
$9,450,000
Captiva, Florida, 33924, United States
$9,450,000
3Beds
0.1Baths
6,559Sqft
Captiva, Florida, 33924, United States
Rare opportunity to purchase a luxurious Gulf Front Estate on Captiva Island within the gated resort community of South Seas. This stunning, coastal property offers 102 of beach frontage w/ breathtaking sunsets and views of the gulf. Totally renovated and remodeled with 5 bedrooms, new quality craftsmanship and attention to every detail.
Michael Polly
$9,450,000
941 South Seas Plantation Dr
3Beds
0.1Baths
6,559Sqft
Captiva, Florida, 33924, United States
Rare opportunity to purchase a luxurious Gulf Front Estate on Captiva Island within the gated resort community of South Seas. This stunning, coastal property offers 102 of beach frontage w/ breathtaking sunsets and views of the gulf. Totally renovated and remodeled with 5 bedrooms, new quality craftsmanship and attention to every detail. All new interior furnishings and amenities include, striking quartzite countertops and custom solid wood cabinetry in the kitchen, coffee bar & primary bathroom, beautiful wide plank wood floor throughout, custom ceiling details, private elevator, laundry w/ lots of storage, powder bath, electric blinds and designer furnishings. The spacious kitchen features a gas Wolf range, beverage cooler, refrigerator, freezer, microwave and dishwasher. Gorgeous views of the beach from the kitchen, dining & great room. The penthouse style primary bedroom features a sitting area, laundry, beautiful bathroom and private deck over look the beach which is perfect for enjoying a morning cup of coffee or evening star gazing with a tropical beverage. Multiple sets of sliders lead to a huge outdoor deck featuring an elevated swimming pool. The structure has concrete pilings, a new standing seam metal roof, impact glass throughout, expansive circular driveway with pavers, tropical landscaping with pops of color and strategically designed low voltage lighting. There is an oversized 2 car garage with room for bikes, beach & fishing gear, a separate golf cart garage, and an epoxy finish on the floor. The bonus area consisting of 2 of the 5 bedrooms and 1 of the 4 bathrooms which is non-conforming is fun for guests and a nice addition to the home. After sun and fun, enjoy the refreshing outdoor shower for a quick rinse before splashing in the pool. This home has it all location and lifestyle.
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Michael Polly
$9,450,000
941 South Seas Plantation Dr
3Beds
0.1Baths
6,559Sqft
$9,450,000
Captiva, Florida, 33924, United States
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