16475 Captiva Dr

A once-in-a-generation opportunity to own one of Captiva Island’s largest and most private bayfront estates—3.5 ACRES of gated serenity with deepwater access, sport courts, and resort-style wellness amenities. Positioned along the coveted Roosevelt Channel, this secluded estate is surrounded by lush, unspoiled nature and offers direct Gulf access with TWO PRIVATE DOCKS—each equipped with lifts, one covered—making it an exceptional find for boating and water enthusiasts. Thoughtfully crafted for both entertaining and retreat-style living, the custom-built home features rich wood flooring, soaring beamed ceilings, and a dramatic beacon tower that floods the great room with natural light. The warm, inviting interior includes a gas fireplace, formal dining room, wood-accented den, and a chef’s kitchen ideal for gathering. A private study provides a quiet retreat for work or reading, and a third bedroom located near the wellness wing offers flexible space for guests, live-in staff, or multigenerational living. TWO GRAND ENSUITE BEDROOMS serve as luxurious personal sanctuaries, each with sitting areas, morning bars, and private laundry closets. Outdoor living is equally impressive, with an expansive Brazilian wood deck overlooking a full-size private TENNIS COURT, BOCCE COURT and outdoor fireplace. A spiral staircase leads to a rooftop hot tub with panoramic views of Captiva’s colorful sunsets and starlit skies. Down by the water, a firepit offers a peaceful place to unwind as boats drift by in the channel. The private indoor wellness wing features a travertine-lined POOL, fully equipped FITNESS ROOM, and personal SAUNA—creating a spa-like experience in the comfort of your own home. Additional features include a three-car garage with workshop, and a chair lift for added accessibility. With 3.5 acres and no HOA restrictions, the property also presents RARE EXPANSION POTENTIAL—whether building additional guesthouses, enhancing outdoor amenities, or creating a multi-generational compound. Whether envisioned as a family legacy estate, a private coastal retreat, or a trophy property for entertaining, this is a rare chance to own one of Captiva Island’s most extraordinary offerings.

*This property is not a listing of Westside Estate Agency. This property is related to the real estate license and real estate activities of Chance King in the U.S. State of Florida under his Florida broker, which is unrelated to the real estate license and real estate activities of Chance King in the U.S. State of California under Westside Estate Agency. Westside Estate Agency is not a licensed broker in the U.S. state of Florida.* 

A once-in-a-generation opportunity to own one of Captiva Island’s largest and most private bayfront estates—3.5 ACRES of gated serenity with deepwater access, sport courts, and resort-style wellness amenities. Positioned along the coveted Roosevelt Channel, this secluded estate is surrounded by lush, unspoiled nature and offers direct Gulf access with TWO PRIVATE DOCKS—each equipped with lifts, one covered—making it an exceptional find for boating and water enthusiasts. Thoughtfully crafted for both entertaining and retreat-style living, the custom-built home features rich wood flooring, soaring beamed ceilings, and a dramatic beacon tower that floods the great room with natural light. The warm, inviting interior includes a gas fireplace, formal dining room, wood-accented den, and a chef’s kitchen ideal for gathering. A private study provides a quiet retreat for work or reading, and a third bedroom located near the wellness wing offers flexible space for guests, live-in staff, or multigenerational living. TWO GRAND ENSUITE BEDROOMS serve as luxurious personal sanctuaries, each with sitting areas, morning bars, and private laundry closets. Outdoor living is equally impressive, with an expansive Brazilian wood deck overlooking a full-size private TENNIS COURT, BOCCE COURT and outdoor fireplace. A spiral staircase leads to a rooftop hot tub with panoramic views of Captiva’s colorful sunsets and starlit skies. Down by the water, a firepit offers a peaceful place to unwind as boats drift by in the channel. The private indoor wellness wing features a travertine-lined POOL, fully equipped FITNESS ROOM, and personal SAUNA—creating a spa-like experience in the comfort of your own home. Additional features include a three-car garage with workshop, and a chair lift for added accessibility. With 3.5 acres and no HOA restrictions, the property also presents RARE EXPANSION POTENTIAL—whether building additional guesthouses, enhancing outdoor amenities, or creating a multi-generational compound. Whether envisioned as a family legacy estate, a private coastal retreat, or a trophy property for entertaining, this is a rare chance to own one of Captiva Island’s most extraordinary offerings.

*This property is not a listing of Westside Estate Agency. This property is related to the real estate license and real estate activities of Chance King in the U.S. State of Florida under his Florida broker, which is unrelated to the real estate license and real estate activities of Chance King in the U.S. State of California under Westside Estate Agency. Westside Estate Agency is not a licensed broker in the U.S. state of Florida.* 

A once-in-a-generation opportunity to own one of Captiva Island’s largest and most private bayfront estates—3.5 ACRES of gated serenity with deepwater access, sport courts, and resort-style wellness amenities. Positioned along the coveted Roosevelt Channel, this secluded estate is surrounded by lush, unspoiled nature and offers direct Gulf access with TWO PRIVATE DOCKS—each equipped with lifts, one covered—making it an exceptional find for boating and water enthusiasts. Thoughtfully crafted for both entertaining and retreat-style living, the custom-built home features rich wood flooring, soaring beamed ceilings, and a dramatic beacon tower that floods the great room with natural light. The warm, inviting interior includes a gas fireplace, formal dining room, wood-accented den, and a chef’s kitchen ideal for gathering. A private study provides a quiet retreat for work or reading, and a third bedroom located near the wellness wing offers flexible space for guests, live-in staff, or multigenerational living. TWO GRAND ENSUITE BEDROOMS serve as luxurious personal sanctuaries, each with sitting areas, morning bars, and private laundry closets. Outdoor living is equally impressive, with an expansive Brazilian wood deck overlooking a full-size private TENNIS COURT, BOCCE COURT and outdoor fireplace. A spiral staircase leads to a rooftop hot tub with panoramic views of Captiva’s colorful sunsets and starlit skies. Down by the water, a firepit offers a peaceful place to unwind as boats drift by in the channel. The private indoor wellness wing features a travertine-lined POOL, fully equipped FITNESS ROOM, and personal SAUNA—creating a spa-like experience in the comfort of your own home. Additional features include a three-car garage with workshop, and a chair lift for added accessibility. With 3.5 acres and no HOA restrictions, the property also presents RARE EXPANSION POTENTIAL—whether building additional guesthouses, enhancing outdoor amenities, or creating a multi-generational compound. Whether envisioned as a family legacy estate, a private coastal retreat, or a trophy property for entertaining, this is a rare chance to own one of Captiva Island’s most extraordinary offerings.

*This property is not a listing of Westside Estate Agency. This property is related to the real estate license and real estate activities of Chance King in the U.S. State of Florida under his Florida broker, which is unrelated to the real estate license and real estate activities of Chance King in the U.S. State of California under Westside Estate Agency. Westside Estate Agency is not a licensed broker in the U.S. state of Florida.*