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.

2026029362 MLS

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

Listing Courtesy of John R. Wood Properties

$10,900,000

Fantastic Private Beachfront Sanctuary located on the Gold Coast of Captiva Island, where timeless craftsmanship meets coastal luxury. Framed by beautiful Royal Palms and lush, mature landscaping, this extraordinary estate is a rare opportunity to own one of Captiva’s most unique and artfully designed properties. A beautifully maintained private boardwalk winds through native foliage, offering quick and effortless access to Captiva’s world-renowned white sand beaches and turquoise waters. The oversized resort-style pool with integrated spa, and expansive covered lounge area creates the perfect environment for laid-back island living or upscale entertaining. Step inside through hand-crafted double doors by renowned sculptor Kim Brandell into a soaring great room, where floor-to-ceiling windows frame postcard-worthy views of the Gulf and surrounding nature. Natural light floods every corner, enhancing the home’s thoughtful architecture and elevated coastal feel. The gourmet kitchen is both functional and stylish, featuring high-end appliances, extensive counter space, a large walk-in pantry, and seamless flow into the main living areas. The spacious VIP suite offers the ultimate retreat—located just off the elevator, it features a private balcony, an expansive sitting/dressing room, floor-to-ceiling windows, and a luxurious bath complete with oversized shower, soaking tub, and custom mirrors. The home is spacious thru out offering private guest suites for your guest and family to enjoy. Additional highlights include concrete construction on pilings, estate zoning (with potential for additional dwellings), huge rec space, generous balcony and deck space on all levels, and panoramic Gulf views throughout. This is not just a home—it’s an experience. A rare blend of serenity, style, and superior design, tucked away in one of Captiva Island’s most coveted settings.

5 Beds ⋅ 6 Baths ⋅ 2026022035 MLS

Fantastic Private Beachfront Sanctuary located on the Gold Coast of Captiva Island, where timeless craftsmanship meets coastal luxury. Framed by beautiful Royal Palms and lush, mature landscaping, this extraordinary estate is a rare opportunity to own one of Captiva’s most unique and artfully designed properties. A beautifully maintained private boardwalk winds through native foliage, offering quick and effortless access to Captiva’s world-renowned white sand beaches and turquoise waters. The oversized resort-style pool with integrated spa, and expansive covered lounge area creates the perfect environment for laid-back island living or upscale entertaining. Step inside through hand-crafted double doors by renowned sculptor Kim Brandell into a soaring great room, where floor-to-ceiling windows frame postcard-worthy views of the Gulf and surrounding nature. Natural light floods every corner, enhancing the home’s thoughtful architecture and elevated coastal feel. The gourmet kitchen is both functional and stylish, featuring high-end appliances, extensive counter space, a large walk-in pantry, and seamless flow into the main living areas. The spacious VIP suite offers the ultimate retreat—located just off the elevator, it features a private balcony, an expansive sitting/dressing room, floor-to-ceiling windows, and a luxurious bath complete with oversized shower, soaking tub, and custom mirrors. The home is spacious thru out offering private guest suites for your guest and family to enjoy. Additional highlights include concrete construction on pilings, estate zoning (with potential for additional dwellings), huge rec space, generous balcony and deck space on all levels, and panoramic Gulf views throughout. This is not just a home—it’s an experience. A rare blend of serenity, style, and superior design, tucked away in one of Captiva Island’s most coveted settings.

16730 Captiva Drive, Captiva

Listing Courtesy of Royal Shell Real Estate, Inc.

$4,350,000

Where timeless island architecture meets modern luxury, this exceptional Captiva retreat offers the rare combination of privacy, craftsmanship, and outstanding income-producing potential. Designed by acclaimed architect Bud Lawrence and situated on a premier corner lot just steps from both the Gulf beach and bay, this 5-bedroom, 5.5-bath residence was built for both relaxed island living and unforgettable entertaining. Surrounded by lush tropical landscaping, the home centers around an impressive two-story screened lanai featuring a PebbleTec heated pool and spa, waterfall, waterslide, expansive covered living areas, and a fully equipped outdoor kitchen with a built-in Thermador grilling station. Whether hosting family gatherings or accommodating large groups, the floor plan is designed to comfortably sleep multiple generations and guests with two private primary suites, three additional guest suites, and elevator access to all levels. Inside, custom craftsmanship is showcased throughout with Brazilian cherry wood flooring, marble finishes, handcrafted Sinker Cypress doors, custom cabinetry, imported roof tiles, decorative precast architectural details, and copper gutters and downspouts. The gourmet kitchen is complemented by dual wine coolers and generous entertaining space, while extensive technology upgrades include a Control4 smart home system, a 140-inch projection screen, surround sound, and integrated outdoor audio. Perfectly positioned in the heart of Captiva Island, owners and guests can easily walk to the beach, bay, restaurants, shops, marinas, and island attractions. With its desirable location, spacious layout, resort-style amenities, and ability to accommodate larger groups, the property also offers exceptional vacation rental potential in one of Southwest Florida's most sought-after island destinations. A rare opportunity to own a distinctive Captiva residence where luxury, location, and lifestyle come together.

5 Beds ⋅ 6 Baths ⋅ 2026024474 MLS

Where timeless island architecture meets modern luxury, this exceptional Captiva retreat offers the rare combination of privacy, craftsmanship, and outstanding income-producing potential. Designed by acclaimed architect Bud Lawrence and situated on a premier corner lot just steps from both the Gulf beach and bay, this 5-bedroom, 5.5-bath residence was built for both relaxed island living and unforgettable entertaining. Surrounded by lush tropical landscaping, the home centers around an impressive two-story screened lanai featuring a PebbleTec heated pool and spa, waterfall, waterslide, expansive covered living areas, and a fully equipped outdoor kitchen with a built-in Thermador grilling station. Whether hosting family gatherings or accommodating large groups, the floor plan is designed to comfortably sleep multiple generations and guests with two private primary suites, three additional guest suites, and elevator access to all levels. Inside, custom craftsmanship is showcased throughout with Brazilian cherry wood flooring, marble finishes, handcrafted Sinker Cypress doors, custom cabinetry, imported roof tiles, decorative precast architectural details, and copper gutters and downspouts. The gourmet kitchen is complemented by dual wine coolers and generous entertaining space, while extensive technology upgrades include a Control4 smart home system, a 140-inch projection screen, surround sound, and integrated outdoor audio. Perfectly positioned in the heart of Captiva Island, owners and guests can easily walk to the beach, bay, restaurants, shops, marinas, and island attractions. With its desirable location, spacious layout, resort-style amenities, and ability to accommodate larger groups, the property also offers exceptional vacation rental potential in one of Southwest Florida's most sought-after island destinations. A rare opportunity to own a distinctive Captiva residence where luxury, location, and lifestyle come together.

15161 Wiles Drive, Captiva

Listing Courtesy of Royal Shell Real Estate, Inc.

$6,995,000

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.

6 Beds ⋅ 5 Baths ⋅ 2026023434 MLS

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 Drive, Captiva

Listing Courtesy of Premier Sotheby's Int'l Realty

$4,500,000

For the first time ever, two contiguous bayfront parcels are being offered together to create an extraordinary 5-acre waterfront compound along the coveted Roosevelt Channel on Captiva Island.

3 Beds ⋅ 4 Baths ⋅ 226018340 MLS

For the first time ever, two contiguous bayfront parcels are being offered together to create an extraordinary 5-acre waterfront compound along the coveted Roosevelt Channel on Captiva Island.

16475/95 Captiva Drive, Captiva

Listing Courtesy of Douglas Elliman Florida,LLC

Selling Office: .

$18,900,000

Arguably the most architecturally significant home to ever be brought to market on Captiva, Bella Luna was nationally recognized for impeccable design when it received the American Institute of Building Design’s (AIBD) prestigious American Residential Design Award (ARDA) in 2021. Conceptualized by the renowned Wayne Visbeen of Visbeen Architects, Bella Luna reflects the exceptional craftsmanship and innovative design for which the firm is celebrated. Known for collaborating with prestigious clients such as Metropolitan Museum of Art, Martha Stewart and Disney, Visbeen Architects brings the same level of artistry and attention to detail to residential projects, making this property a masterpiece of design and livability. Constructed to be a fortress of concrete and steel, the substantial nature of the structure is resilient yet refined. Employing hotel and hospitality design techniques, every detail was meticulously tailored to enhance human experience through sophistication and functionality, creating intimate experiences within the grandeur of larger spaces. A feature sheet is available detailing the extensive upgrades, features and breathtaking attributes.

6 Beds ⋅ 7 Baths ⋅ 2026006271 MLS

Arguably the most architecturally significant home to ever be brought to market on Captiva, Bella Luna was nationally recognized for impeccable design when it received the American Institute of Building Design’s (AIBD) prestigious American Residential Design Award (ARDA) in 2021. Conceptualized by the renowned Wayne Visbeen of Visbeen Architects, Bella Luna reflects the exceptional craftsmanship and innovative design for which the firm is celebrated. Known for collaborating with prestigious clients such as Metropolitan Museum of Art, Martha Stewart and Disney, Visbeen Architects brings the same level of artistry and attention to detail to residential projects, making this property a masterpiece of design and livability. Constructed to be a fortress of concrete and steel, the substantial nature of the structure is resilient yet refined. Employing hotel and hospitality design techniques, every detail was meticulously tailored to enhance human experience through sophistication and functionality, creating intimate experiences within the grandeur of larger spaces. A feature sheet is available detailing the extensive upgrades, features and breathtaking attributes.

16950 Captiva Drive, Captiva

Listing Courtesy of Premier Sotheby's Int'l Realty

$4,875,000

Beachfront on Captiva - 1.07 acres of pristine beachfront on one of the Gulf Coast’s most exclusive islands, Captiva Island. Imagine owning 106 feet of direct Gulf Frontage and highly desirable Western Exposure, this rare homesite offers unobstructed sunsets, endless water views, and the soothing sound of waves meeting the white sand shoreline. One of only a handful of remaining buildable beachfront parcels on Captiva’s famed Gold Coast, this exceptional property provides the scale and privacy to create a luxury coastal estate or multi-generational family compound, a lifestyle that is increasingly rare in today’s market. Envision a custom residence with an expansive pool and spa overlooking the Gulf, morning shelling walks, world-class fishing, and tranquil evenings framed by colorful sunsets and the sea breeze flowing through your future home. The property is surveyed and includes professionally designed building plans for a stunning 7,995 SF multi-level residence with a second-floor pool and separate guest quarters, offering a virtually shovel-ready opportunity or the freedom to design your own coastal retreat. With over 400 feet of depth and natural privacy from Captiva Drive, it is ideal for creating a secluded beachfront retreat while remaining close to the island’s village. Just a short stroll to Andy Rosse Lane, the heart of Captiva’s charming and laid-back lifestyle, with boutique shops, waterfront dining, and iconic restaurants such as The Mucky Duck, The Bubble Room, Green Flash, and Old Captiva House. Enjoy nearby marinas, watersports, South Seas Island Resort and Golf Course, Tween Waters Inn & Marina, and miles of unspoiled white sand beaches, all within a stroll of your future home. Captiva provides an unhurried island setting with no traffic lights or commercial congestion. The ideal setting for a private island retreat, yet conveniently located just a short drive from RSW International Airport, Page Field for private aviation, and Naples, offering world-class fine dining, luxury shopping, and cultural amenities. This is a truly irreplaceable Gulf-front estate parcel in one of Florida’s most prestigious luxury real estate markets, offering scale, flexibility, privacy, and direct beach frontage that is rarely available on Captiva Island or the Sanibel barrier islands. A premier opportunity to build a legacy property on the Gold Coast of Southwest Florida’s Gulf Coast.

2026003811 MLS

Beachfront on Captiva - 1.07 acres of pristine beachfront on one of the Gulf Coast’s most exclusive islands, Captiva Island. Imagine owning 106 feet of direct Gulf Frontage and highly desirable Western Exposure, this rare homesite offers unobstructed sunsets, endless water views, and the soothing sound of waves meeting the white sand shoreline. One of only a handful of remaining buildable beachfront parcels on Captiva’s famed Gold Coast, this exceptional property provides the scale and privacy to create a luxury coastal estate or multi-generational family compound, a lifestyle that is increasingly rare in today’s market. Envision a custom residence with an expansive pool and spa overlooking the Gulf, morning shelling walks, world-class fishing, and tranquil evenings framed by colorful sunsets and the sea breeze flowing through your future home. The property is surveyed and includes professionally designed building plans for a stunning 7,995 SF multi-level residence with a second-floor pool and separate guest quarters, offering a virtually shovel-ready opportunity or the freedom to design your own coastal retreat. With over 400 feet of depth and natural privacy from Captiva Drive, it is ideal for creating a secluded beachfront retreat while remaining close to the island’s village. Just a short stroll to Andy Rosse Lane, the heart of Captiva’s charming and laid-back lifestyle, with boutique shops, waterfront dining, and iconic restaurants such as The Mucky Duck, The Bubble Room, Green Flash, and Old Captiva House. Enjoy nearby marinas, watersports, South Seas Island Resort and Golf Course, Tween Waters Inn & Marina, and miles of unspoiled white sand beaches, all within a stroll of your future home. Captiva provides an unhurried island setting with no traffic lights or commercial congestion. The ideal setting for a private island retreat, yet conveniently located just a short drive from RSW International Airport, Page Field for private aviation, and Naples, offering world-class fine dining, luxury shopping, and cultural amenities. This is a truly irreplaceable Gulf-front estate parcel in one of Florida’s most prestigious luxury real estate markets, offering scale, flexibility, privacy, and direct beach frontage that is rarely available on Captiva Island or the Sanibel barrier islands. A premier opportunity to build a legacy property on the Gold Coast of Southwest Florida’s Gulf Coast.

16970 Captiva Drive, Captiva

Listing Courtesy of Compass Florida LLC

Selling Office: .

$5,699,000

A rare Gulf-front estate opportunity on Captiva Island featuring approximately 100 feet of direct beachfront and estate owned multifamily entitlement, a combination virtually impossible to replicate under current zoning and coastal regulations. The property includes a 3 bedrooms, 3 baths main home with a 2 bedroom guest home, private pool, detached garage and beachside cabana and screened gazebo. The estate zoning with multifamily use sets this property apart for a custom legacy residence, multigenerational compound, or future redevelopment, while preserving the low density character of this stretch of Captiva Drive. Opportunities of this scale, frontage, and zoning are exceedingly limited and rarely come to market. A grandfathered shared bulkhead adds lasting value and provides direct bay access. Positioned among Captiva’s most notable properties, this estate parcel delivers exceptional value to renovate or explore redevelopment opportunities!

5 Beds ⋅ 4 Baths ⋅ 2026002529 MLS

A rare Gulf-front estate opportunity on Captiva Island featuring approximately 100 feet of direct beachfront and estate owned multifamily entitlement, a combination virtually impossible to replicate under current zoning and coastal regulations. The property includes a 3 bedrooms, 3 baths main home with a 2 bedroom guest home, private pool, detached garage and beachside cabana and screened gazebo. The estate zoning with multifamily use sets this property apart for a custom legacy residence, multigenerational compound, or future redevelopment, while preserving the low density character of this stretch of Captiva Drive. Opportunities of this scale, frontage, and zoning are exceedingly limited and rarely come to market. A grandfathered shared bulkhead adds lasting value and provides direct bay access. Positioned among Captiva’s most notable properties, this estate parcel delivers exceptional value to renovate or explore redevelopment opportunities!

16632 Captiva Drive, Captiva

Listing Courtesy of Kingfisher Real Estate, Inc.

$1,750,000

Welcome to your Captiva Island oasis! This Gorgeous home is the perfect island get-a-way- situated on Roosevelt channel offering direct Gulf access from your private dock and a rare boathouse with 20,000lb. boat lift- the natural shoreline adds privacy and allows for a great kayak/SUP launch area. Just a short stroll to one of the best beaches and shelling locations! This 3 bedroom, 3 bath, pool home has Travertine floors throughout main living level and hardwood floors in the private, 2nd floor primary suite. The primary suite has vaulted/beamed ceiling & a private sunning deck w/water views. Primary bathroom has double sinks and custom glass tile. The kitchen has been completely renovated and cleverly designed to maximize storage and flow in the main living area, adding a custom island and space for a 60" range and hood, custom built-ins added in all bedroom closets, this home is light, bright and everything you want in an island home. After a day on the water, take a swim in the sparkling concrete elevated pool surrounded by lush tropical vegetation offering a feeling of seclusion and privacy. Newer Septic system, 2 a/c's 2022, washer & dryer 2025. Enjoy Island living, boating, fishing, shelling, sunning and stunning sunsets on Captiva Island. Property sold furnished, main living area and bedroom images are virtually staged adding accessories and artwork. Furniture is in place. 60" Range and hood in kitchen is virtually staged, propane tank installed and piped ready for range to be installed.

3 Beds ⋅ 3 Baths ⋅ 2025026419 MLS

Welcome to your Captiva Island oasis! This Gorgeous home is the perfect island get-a-way- situated on Roosevelt channel offering direct Gulf access from your private dock and a rare boathouse with 20,000lb. boat lift- the natural shoreline adds privacy and allows for a great kayak/SUP launch area. Just a short stroll to one of the best beaches and shelling locations! This 3 bedroom, 3 bath, pool home has Travertine floors throughout main living level and hardwood floors in the private, 2nd floor primary suite. The primary suite has vaulted/beamed ceiling & a private sunning deck w/water views. Primary bathroom has double sinks and custom glass tile. The kitchen has been completely renovated and cleverly designed to maximize storage and flow in the main living area, adding a custom island and space for a 60" range and hood, custom built-ins added in all bedroom closets, this home is light, bright and everything you want in an island home. After a day on the water, take a swim in the sparkling concrete elevated pool surrounded by lush tropical vegetation offering a feeling of seclusion and privacy. Newer Septic system, 2 a/c's 2022, washer & dryer 2025. Enjoy Island living, boating, fishing, shelling, sunning and stunning sunsets on Captiva Island. Property sold furnished, main living area and bedroom images are virtually staged adding accessories and artwork. Furniture is in place. 60" Range and hood in kitchen is virtually staged, propane tank installed and piped ready for range to be installed.

16813 Captiva Drive, Captiva

Listing Courtesy of John R. Wood Properties

Selling Office: .

$4,749,000

Experience the timeless coastal allure of 15160 Captiva Drive, a stunning estate designed with a rare reverse floor plan to capture sweeping bay views from its multi-level decks. This 6-bedroom + den, 6.5-bath residence offers more than 4,800 square feet of refined living space, blending elevated design with effortless island living. Crafted in Coastal-Tuscan style, the home showcases travertine flooring in the main living areas, warm wood flooring in the bedrooms, and soaring 10+ ft ceilings with detailed crown molding. The thoughtful layout features multiple living rooms, all ensuite bedrooms, an elevator, a morning kitchen, and a private in-law suite—ideal for hosting with comfort and privacy in mind. The chef’s kitchen is beautifully appointed with a gas cooktop, stainless steel appliances, granite countertops with breakfast bar seating, custom wood cabinetry, a walk-in pantry, oversized sink, and a dedicated bar area for seamless entertaining. Step outside and enjoy the best of the #IslandLifestyle with a private pool and spa, spacious covered and open patios, and effortless beach access just a short walk away. Perfectly positioned near Captiva Village, beloved island restaurants, and boutique shopping, this residence embraces everything that defines the #CaptivaLifestyle.

6 Beds ⋅ 7 Baths ⋅ 2025024133 MLS

Experience the timeless coastal allure of 15160 Captiva Drive, a stunning estate designed with a rare reverse floor plan to capture sweeping bay views from its multi-level decks. This 6-bedroom + den, 6.5-bath residence offers more than 4,800 square feet of refined living space, blending elevated design with effortless island living. Crafted in Coastal-Tuscan style, the home showcases travertine flooring in the main living areas, warm wood flooring in the bedrooms, and soaring 10+ ft ceilings with detailed crown molding. The thoughtful layout features multiple living rooms, all ensuite bedrooms, an elevator, a morning kitchen, and a private in-law suite—ideal for hosting with comfort and privacy in mind. The chef’s kitchen is beautifully appointed with a gas cooktop, stainless steel appliances, granite countertops with breakfast bar seating, custom wood cabinetry, a walk-in pantry, oversized sink, and a dedicated bar area for seamless entertaining. Step outside and enjoy the best of the #IslandLifestyle with a private pool and spa, spacious covered and open patios, and effortless beach access just a short walk away. Perfectly positioned near Captiva Village, beloved island restaurants, and boutique shopping, this residence embraces everything that defines the #CaptivaLifestyle.

15160 Captiva Drive, Captiva

Listing Courtesy of John R. Wood Properties

$5,650,000

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.

2025013467 MLS

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.

16548 Captiva Drive, Captiva

Listing Courtesy of Royal Shell Real Estate, Inc.

$9,700,000

This meticulously refined Gulf-front estate embodies the essence of tropical luxury—where timeless craftsmanship meets modern elegance. Thoughtfully enhanced over time, SOUTH HAVEN blends comfort, sophistication, and functionality at every turn. Recent updates include a redesigned kitchen and dining area, a reimagined primary bath, and a new roof (2023), along with premium finishes and fixtures throughout. The main level welcomes you with a sun-filled foyer leading to multiple guest suites, including a dual guest wing for added privacy. The chef-inspired kitchen combines contemporary design with coastal warmth, opening to a bright dining alcove ideal for gatherings. The living room frames uninterrupted Gulf views, creating a serene backdrop for every moment. Upstairs, the owner’s suite commands sweeping ocean vistas and features a stone-clad electric fireplace, woven flooring, and a tranquil, spa-like ambiance. The ground level includes a spacious garage, flexible-use spaces, and elevator access to all floors for effortless convenience. Outdoors, the estate is graced by towering Royal Palms, a resort-style pool with sun shelf, and covered lounging and dining areas designed for relaxed entertaining. Beyond the pool, a private beachside yard with manicured greens, a seaside walkway, and a charming shorefront cabana completes the coastal experience. From its refined architecture to its breathtaking sunsets, South Haven stands as a true Captiva masterpiece—where every detail celebrates the art of island living.

5 Beds ⋅ 5 Baths ⋅ 2025014681 MLS

This meticulously refined Gulf-front estate embodies the essence of tropical luxury—where timeless craftsmanship meets modern elegance. Thoughtfully enhanced over time, SOUTH HAVEN blends comfort, sophistication, and functionality at every turn. Recent updates include a redesigned kitchen and dining area, a reimagined primary bath, and a new roof (2023), along with premium finishes and fixtures throughout. The main level welcomes you with a sun-filled foyer leading to multiple guest suites, including a dual guest wing for added privacy. The chef-inspired kitchen combines contemporary design with coastal warmth, opening to a bright dining alcove ideal for gatherings. The living room frames uninterrupted Gulf views, creating a serene backdrop for every moment. Upstairs, the owner’s suite commands sweeping ocean vistas and features a stone-clad electric fireplace, woven flooring, and a tranquil, spa-like ambiance. The ground level includes a spacious garage, flexible-use spaces, and elevator access to all floors for effortless convenience. Outdoors, the estate is graced by towering Royal Palms, a resort-style pool with sun shelf, and covered lounging and dining areas designed for relaxed entertaining. Beyond the pool, a private beachside yard with manicured greens, a seaside walkway, and a charming shorefront cabana completes the coastal experience. From its refined architecture to its breathtaking sunsets, South Haven stands as a true Captiva masterpiece—where every detail celebrates the art of island living.

16770 Captiva Drive, Captiva

Listing Courtesy of John R. Wood Properties

$11,500,000

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 island's renowned restaurants, shopping, and recreational activities. The property's 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 Captiva's pristine Gulf beaches. Multiple covered and open terraces provide the perfect setting to enjoy spectacular sunsets and the island's 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 Captiva's 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.

6 Beds ⋅ 8 Baths ⋅ 2025006303 MLS

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 island's renowned restaurants, shopping, and recreational activities. The property's 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 Captiva's pristine Gulf beaches. Multiple covered and open terraces provide the perfect setting to enjoy spectacular sunsets and the island's 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 Captiva's 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.

17030 Captiva Drive, Captiva

Listing Courtesy of Royal Shell Real Estate, Inc.

$1,600,000

Welcome to "Wade On In," a beautifully remodeled Captiva Island retreat and prime investment opportunity with proven success in weekly rentals. Previously known as "On the Wiles Side," this home features lush, tropical landscaping that complements the island setting. Just a 2-minute stroll to Captiva Beach, The open floor plan boasts vaulted ceilings, an inviting kitchen, and a spacious master suite with well-appointed guest rooms. Outside, the large pool area is a private oasis with lounge seating, a dining area, and grill. Enjoy corn hole or relax on pool floats, then transition to the screened front porch for a cool drink. It’s equipped for a turnkey beach experience, including beach chairs, umbrellas, a wagon,and toys for the kids. With shops and restaurants a short walk or golf cart ride away, "Wade On In"embodies the best of Captiva living and offers exceptional rental income potential.

3 Beds ⋅ 2 Baths ⋅ 224089966 MLS

Welcome to "Wade On In," a beautifully remodeled Captiva Island retreat and prime investment opportunity with proven success in weekly rentals. Previously known as "On the Wiles Side," this home features lush, tropical landscaping that complements the island setting. Just a 2-minute stroll to Captiva Beach, The open floor plan boasts vaulted ceilings, an inviting kitchen, and a spacious master suite with well-appointed guest rooms. Outside, the large pool area is a private oasis with lounge seating, a dining area, and grill. Enjoy corn hole or relax on pool floats, then transition to the screened front porch for a cool drink. It’s equipped for a turnkey beach experience, including beach chairs, umbrellas, a wagon,and toys for the kids. With shops and restaurants a short walk or golf cart ride away, "Wade On In"embodies the best of Captiva living and offers exceptional rental income potential.

15155 Wiles Drive, Captiva

Listing Courtesy of Royal Shell Real Estate, Inc.

Selling Office: .

$6,900,000

Rare Beachfront Estate with Separate Guest Home on Captiva Island Seize the rare opportunity to own a private beachfront estate on the coveted Gold Coast of Captiva Island. Nestled on over an acre of land, this exquisite property features a breathtaking architectural design that seamlessly blends with nature, maximizing panoramic waterfront views and enhancing the exceptional outdoor living experience. The main home has been meticulously remodeled with high-end finishes, offering soaring beamed ceilings, an elevator, two-master suites and multiple garage spaces and storage areas. The open layout invites abundant natural light, providing an ideal setting for entertaining or relaxing with family. The separate two-bedroom guest home boasts a private lanai and its own garage, offering comfort and privacy for visitors or extended family. With 100 feet of pristine Gulf of Mexico beachfront, this estate is a rare gem on the island, situated amidst award-winning beaches. The expansive property offers unparalleled privacy and direct access to Captiva’s renowned natural beauty. Don’t miss out on this exceptional piece of Captiva Island paradise!

5 Beds ⋅ 5 Baths ⋅ 225026465 MLS

Rare Beachfront Estate with Separate Guest Home on Captiva Island Seize the rare opportunity to own a private beachfront estate on the coveted Gold Coast of Captiva Island. Nestled on over an acre of land, this exquisite property features a breathtaking architectural design that seamlessly blends with nature, maximizing panoramic waterfront views and enhancing the exceptional outdoor living experience. The main home has been meticulously remodeled with high-end finishes, offering soaring beamed ceilings, an elevator, two-master suites and multiple garage spaces and storage areas. The open layout invites abundant natural light, providing an ideal setting for entertaining or relaxing with family. The separate two-bedroom guest home boasts a private lanai and its own garage, offering comfort and privacy for visitors or extended family. With 100 feet of pristine Gulf of Mexico beachfront, this estate is a rare gem on the island, situated amidst award-winning beaches. The expansive property offers unparalleled privacy and direct access to Captiva’s renowned natural beauty. Don’t miss out on this exceptional piece of Captiva Island paradise!

16886 Captiva Drive, Captiva

Listing Courtesy of Kingfisher Real Estate, Inc.

$3,250,000

Own this little adorable Captiva beach cottage OR "IMAGINE" and build something incrediably special like the coastal modern masterpiece shown. Displayed are Conceptual renderings of what you could build on this property. You get to decide! Enjoy this adorable beach cottage or build a new coastal modern "Landmark" getaway. Whats offered at this price is this charming seaside retreat showcases a open layout w/expansive glass sliders that open onto a large deck, offering breathtaking views of the Gulf of Mexico. Nestled just steps away from the Blind Pass bridge, where Sanibel/Captiva converge, Coquina Cottage proudly stands as the first residence on Captiva beach, establishing itself as a landmark destination. With its panoramic beach views, this idyllic getaway boasts a compact yet well-equipped kitchen, two cozy sleeping areas, & a soothing spa. Set on a half-acre waterfront property w/a single dwelling along the Gulf, the cottage is enveloped by tropical native vegetation. Enjoy exceptional fishing, observe marine life & wildlife, indulge in world-class shelling, & enjoy enchanting sunsets on the white sand beach of Captiva.

2 Beds ⋅ 2 Baths ⋅ 223036615 MLS

Own this little adorable Captiva beach cottage OR "IMAGINE" and build something incrediably special like the coastal modern masterpiece shown. Displayed are Conceptual renderings of what you could build on this property. You get to decide! Enjoy this adorable beach cottage or build a new coastal modern "Landmark" getaway. Whats offered at this price is this charming seaside retreat showcases a open layout w/expansive glass sliders that open onto a large deck, offering breathtaking views of the Gulf of Mexico. Nestled just steps away from the Blind Pass bridge, where Sanibel/Captiva converge, Coquina Cottage proudly stands as the first residence on Captiva beach, establishing itself as a landmark destination. With its panoramic beach views, this idyllic getaway boasts a compact yet well-equipped kitchen, two cozy sleeping areas, & a soothing spa. Set on a half-acre waterfront property w/a single dwelling along the Gulf, the cottage is enveloped by tropical native vegetation. Enjoy exceptional fishing, observe marine life & wildlife, indulge in world-class shelling, & enjoy enchanting sunsets on the white sand beach of Captiva.

17170 Captiva Drive, Captiva

Listing Courtesy of Royal Shell Real Estate, Inc.

$12,500,000

The Crown Jewel of Captiva Island, the one and only Sandpiper Estate. For the first time ever, the iconic Sandpiper Estate is available for purchase, presenting an extraordinary opportunity to own a legacy property on Captiva Island’s prestigious Gold Coast. Spanning 200 feet of prime sandy beach frontage, this breathtaking estate is a rare sanctuary where timeless elegance meets coastal tranquility. Designed for privacy, relaxation, and entertaining, the estate has been cherished for over 40 years as a treasured family retreat and now, it’s ready for its next fortunate owner. The main residence is a masterpiece of waterfront luxury, featuring 3-4 private bedrooms, a spacious central gathering area, and a fantastic kitchen with panoramic Gulf views. A grand dining area offers an elegant setting for entertaining, while a private study provides a quiet retreat. The home seamlessly blends indoor and outdoor living, with an expansive screened lanai, multiple lounging decks, and breathtaking views from every angle. The outdoor spaces feel like a private resort, complete with a spectacular pool area offering unparalleled privacy and stunning waterfront views. Just off the pool, a charming beachside bungalow provides additional accommodations with two guest suites, each with en-suite baths, and a spacious family room for relaxing by the shore. The estate also includes a private tennis court, an additional 2 Br guest house or caretakers quarters, and lush tropical landscaping, creating a secluded and serene retreat. For those seeking the ultimate private estate, two adjacent properties, owned by this same owner, 16548 Captiva Drive and 16543 Captiva Drive are also available, allowing for the creation of an unmatched beach to bay front compound that offers a total of 300 ft of beach frontage, 100 ft of bay frontage with well over 5.25 acres total. This opportunity is more than a home; its a once-in-a-lifetime opportunity to own an iconic piece of Captiva Island.

5 Beds ⋅ 6 Baths ⋅ 225024734 MLS

The Crown Jewel of Captiva Island, the one and only Sandpiper Estate. For the first time ever, the iconic Sandpiper Estate is available for purchase, presenting an extraordinary opportunity to own a legacy property on Captiva Island’s prestigious Gold Coast. Spanning 200 feet of prime sandy beach frontage, this breathtaking estate is a rare sanctuary where timeless elegance meets coastal tranquility. Designed for privacy, relaxation, and entertaining, the estate has been cherished for over 40 years as a treasured family retreat and now, it’s ready for its next fortunate owner. The main residence is a masterpiece of waterfront luxury, featuring 3-4 private bedrooms, a spacious central gathering area, and a fantastic kitchen with panoramic Gulf views. A grand dining area offers an elegant setting for entertaining, while a private study provides a quiet retreat. The home seamlessly blends indoor and outdoor living, with an expansive screened lanai, multiple lounging decks, and breathtaking views from every angle. The outdoor spaces feel like a private resort, complete with a spectacular pool area offering unparalleled privacy and stunning waterfront views. Just off the pool, a charming beachside bungalow provides additional accommodations with two guest suites, each with en-suite baths, and a spacious family room for relaxing by the shore. The estate also includes a private tennis court, an additional 2 Br guest house or caretakers quarters, and lush tropical landscaping, creating a secluded and serene retreat. For those seeking the ultimate private estate, two adjacent properties, owned by this same owner, 16548 Captiva Drive and 16543 Captiva Drive are also available, allowing for the creation of an unmatched beach to bay front compound that offers a total of 300 ft of beach frontage, 100 ft of bay frontage with well over 5.25 acres total. This opportunity is more than a home; its a once-in-a-lifetime opportunity to own an iconic piece of Captiva Island.

16530 Captiva Drive, Captiva

Listing Courtesy of Royal Shell Real Estate, Inc.

$3,125,000

Discover the ultimate Artist retreat with this exceptional 1.4-acre bay front estate parcel on Captiva’s 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!

3 Beds ⋅ 4 Baths ⋅ 225019730 MLS

Discover the ultimate Artist retreat with this exceptional 1.4-acre bay front estate parcel on Captiva’s 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!

16891 Captiva Drive, Captiva

Listing Courtesy of Kingfisher Real Estate, Inc.

Selling Office: .

$3,750,000

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.

3 Beds ⋅ 3 Baths ⋅ 225029219 MLS

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 Drive, Captiva

Listing Courtesy of Royal Shell Real Estate, Inc.

$9,450,000

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.

6 Beds ⋅ 7 Baths ⋅ 224082961 MLS

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 Drive, Captiva

Listing Courtesy of Kingfisher Real Estate, Inc.

$7,900,000

Discover the pinnacle of private Gulf-front living along Captiva Island’s exclusive Gold Coast. This magnificent gated estate is a rare and extraordinary beachfront sanctuary, offering a seamless blend of seclusion, sophistication, and breathtaking natural beauty. Set on a one-of-a-kind parcel with direct access to Captiva’s pristine sugar-sand beaches, this remarkable family compound delivers an unrivaled connection to the turquoise waters of the Gulf of Mexico and awe-inspiring sunsets. The grand main residence boasts six bedrooms and six-and-a-half baths, each crafted with exquisite architectural details and unparalleled craftsmanship. A two-story great room with soaring coffered ceilings, a gas fireplace, and panoramic Gulf views creates a dramatic yet inviting atmosphere. The formal dining room is elegantly appointed, while the gourmet kitchen is a chef’s dream, fully equipped with top-tier appliances and custom finishes. A one-of-a-kind, hand-painted private elevator adds an artistic touch to this coastal masterpiece. Designed for both privacy and indulgence, each bedroom suite features private balconies and screened lanais, providing serene Gulf breezes and unobstructed sunset views. The primary retreat is a sanctuary unto itself, offering his-and-her spa-inspired baths, a soaking tub, dual showers, double vanities, a morning bar, and expansive walk-in closets. Step onto your private screened lanai and take in the breathtaking ocean vistas as the waves roll onto the shore. An expansive coquina stone veranda surrounds the heated saltwater pool and spa, creating the perfect setting for luxurious outdoor living and entertaining. Six conveniently placed laundry rooms add to the home’s seamless functionality. The oversized two-car garage offers massive storage beneath the home for added convenience. A charming guest cottage enhances the estate, featuring two en-suite bedrooms, a full kitchen with breakfast bar, a spacious living area, and a private covered terrace. Additional amenities include two garages at the guest house, a large workshop, and ample storage space for all your island essentials. This exclusive beachfront oasis embodies the epitome of island luxury. Whether you seek a private sanctuary or an entertainer’s dream retreat, this Captiva estate is truly a rare gem that exceeds expectations....your paradise awaits. PROPERTY CAN BE PURCHASED WITH 16475 CAPTIVA DRIVE FOR A RARE GULF TO BAY OPPORTUNITY!

6 Beds ⋅ 9 Baths ⋅ 225008480 MLS

Discover the pinnacle of private Gulf-front living along Captiva Island’s exclusive Gold Coast. This magnificent gated estate is a rare and extraordinary beachfront sanctuary, offering a seamless blend of seclusion, sophistication, and breathtaking natural beauty. Set on a one-of-a-kind parcel with direct access to Captiva’s pristine sugar-sand beaches, this remarkable family compound delivers an unrivaled connection to the turquoise waters of the Gulf of Mexico and awe-inspiring sunsets. The grand main residence boasts six bedrooms and six-and-a-half baths, each crafted with exquisite architectural details and unparalleled craftsmanship. A two-story great room with soaring coffered ceilings, a gas fireplace, and panoramic Gulf views creates a dramatic yet inviting atmosphere. The formal dining room is elegantly appointed, while the gourmet kitchen is a chef’s dream, fully equipped with top-tier appliances and custom finishes. A one-of-a-kind, hand-painted private elevator adds an artistic touch to this coastal masterpiece. Designed for both privacy and indulgence, each bedroom suite features private balconies and screened lanais, providing serene Gulf breezes and unobstructed sunset views. The primary retreat is a sanctuary unto itself, offering his-and-her spa-inspired baths, a soaking tub, dual showers, double vanities, a morning bar, and expansive walk-in closets. Step onto your private screened lanai and take in the breathtaking ocean vistas as the waves roll onto the shore. An expansive coquina stone veranda surrounds the heated saltwater pool and spa, creating the perfect setting for luxurious outdoor living and entertaining. Six conveniently placed laundry rooms add to the home’s seamless functionality. The oversized two-car garage offers massive storage beneath the home for added convenience. A charming guest cottage enhances the estate, featuring two en-suite bedrooms, a full kitchen with breakfast bar, a spacious living area, and a private covered terrace. Additional amenities include two garages at the guest house, a large workshop, and ample storage space for all your island essentials. This exclusive beachfront oasis embodies the epitome of island luxury. Whether you seek a private sanctuary or an entertainer’s dream retreat, this Captiva estate is truly a rare gem that exceeds expectations....your paradise awaits. PROPERTY CAN BE PURCHASED WITH 16475 CAPTIVA DRIVE FOR A RARE GULF TO BAY OPPORTUNITY!

16486/488 Captiva Drive, Captiva

Listing Courtesy of Douglas Elliman Florida,LLC

Selling Office: .

$10,000,000

Captiva!!

4 Beds ⋅ 6 Baths ⋅ 224105230 MLS

Captiva!!

16310 Captiva Drive, Captiva

Listing Courtesy of Kingfisher Real Estate, Inc.

Selling Office: .

$910,000

Situated mid-street on Wightman Lane, this prime location offers quick access to the beach, just a shortstroll away. Previously known as Rick's Retreat, this was a highly popular weekly rental, and its landvalue is undeniable. The home has been remediated, allowing new owners the option to either renovatefor immediate rental potential or start fresh and build their custom Captiva retreat. Wightman Lane is atrue gem, offering easy access to Captiva’s best restaurants, shops, and attractions—all easily exploredby golf cart. This is an exceptional opportunity to invest in one of the island's most desirable locationswith endless possibilities.

3 Beds ⋅ 2 Baths ⋅ 224083813 MLS

Situated mid-street on Wightman Lane, this prime location offers quick access to the beach, just a shortstroll away. Previously known as Rick's Retreat, this was a highly popular weekly rental, and its landvalue is undeniable. The home has been remediated, allowing new owners the option to either renovatefor immediate rental potential or start fresh and build their custom Captiva retreat. Wightman Lane is atrue gem, offering easy access to Captiva’s best restaurants, shops, and attractions—all easily exploredby golf cart. This is an exceptional opportunity to invest in one of the island's most desirable locationswith endless possibilities.

11527 Wightman Lane, Captiva

Listing Courtesy of Royal Shell Real Estate, Inc.

Selling Office: .