$2,695,000 Welcome to your private island retreat on Captiva Island, where tropical elegance, direct boating access, and beachside livingcome together in one extraordinary property. Nestled amid lush native landscaping and swaying palms, this waterfront home offers the rarecombination of private dockage, direct boating access to the Gulf waters and surrounding islands, and beach access with parking just stepsaway at Blind Pass. Designed to embrace the beauty of its island surroundings, the residence exudes timeless coastal charm with bright,light-filled interiors, soaring ceilings, arched windows and doors, and seamless indoor-outdoor living. Outside, a resort-style pool issurrounded by mature tropical gardens, creating a peaceful sanctuary for relaxation and entertaining. A private dock tucked along the naturalshoreline provides a serene setting for launching a boat, kayak, or paddleboard. From the private dock, enjoy direct boating access viaRoosevelt Channel to Pine Island Sound, the Gulf of Mexico, North Captiva, Cayo Costa, and world-class fishing, shelling, cruising, andwaterfront dining destinations throughout Southwest Florida. Whether setting out for a day on the water or exploring nearby islands, thisexceptional location offers the very best of the island boating lifestyle. Thoughtfully designed with four spacious bedrooms and multiple deckspaces on either side of the home, the residence offers inviting places to relax and take in the tropical surroundings. Wonderfully appointedwith an eclectic island vibe, it perfectly captures the laid-back elegance that defines Captiva living. The residence has also enjoyed a stronghistory as a successful vacation rental, offering owners the ability to offset carrying costs while preserving flexibility for personal use.Whether you're enjoying sunrise walks along Captiva's pristine beaches, afternoons on the water, or evenings by the pool beneath the palms,this exceptional property captures the essence of island living. Private, tranquil, and surrounded by nature, it is a rare opportunity to own atrue Captiva Island retreat where boating, beach, and investment potential meet. 4 Beds ⋅ 4 Baths ⋅ 2026028828 MLS Welcome to your private island retreat on Captiva Island, where tropical elegance, direct boating access, and beachside livingcome together in one extraordinary property. Nestled amid lush native landscaping and swaying palms, this waterfront home offers the rarecombination of private dockage, direct boating access to the Gulf waters and surrounding islands, and beach access with parking just stepsaway at Blind Pass. Designed to embrace the beauty of its island surroundings, the residence exudes timeless coastal charm with bright,light-filled interiors, soaring ceilings, arched windows and doors, and seamless indoor-outdoor living. Outside, a resort-style pool issurrounded by mature tropical gardens, creating a peaceful sanctuary for relaxation and entertaining. A private dock tucked along the naturalshoreline provides a serene setting for launching a boat, kayak, or paddleboard. From the private dock, enjoy direct boating access viaRoosevelt Channel to Pine Island Sound, the Gulf of Mexico, North Captiva, Cayo Costa, and world-class fishing, shelling, cruising, andwaterfront dining destinations throughout Southwest Florida. Whether setting out for a day on the water or exploring nearby islands, thisexceptional location offers the very best of the island boating lifestyle. Thoughtfully designed with four spacious bedrooms and multiple deckspaces on either side of the home, the residence offers inviting places to relax and take in the tropical surroundings. Wonderfully appointedwith an eclectic island vibe, it perfectly captures the laid-back elegance that defines Captiva living. The residence has also enjoyed a stronghistory as a successful vacation rental, offering owners the ability to offset carrying costs while preserving flexibility for personal use.Whether you're enjoying sunrise walks along Captiva's pristine beaches, afternoons on the water, or evenings by the pool beneath the palms,this exceptional property captures the essence of island living. Private, tranquil, and surrounded by nature, it is a rare opportunity to own atrue Captiva Island retreat where boating, beach, and investment potential meet. 16785 Captiva Drive, Captiva
$875,000 Highly sought-after, updated 3 bed, 3 bath two-story villa stands apart with rare features not found in other Bayside units, overlooking the tranquil waters of Pine Island Sound, where unchanging estuary views and native wildlife create a peaceful, elevated backdrop—just moments from the best of Captiva Island. Rare features of this top-floor unit include a walk-in pantry—an uncommon luxury in Bayside 3-bedroom villas—all-new hurricane-impact windows and sliders, and a residence that has been gently used as a private second home and never enrolled in a rental program—an added advantage in condition and care. Whether enjoyed as a private island retreat or leveraged as a high-performing investment, this residence offers rare flexibility within a renter-friendly community and stands as one of the least expensive 3-bedroom opportunities on Captiva. The interior is anchored by an updated kitchen with quartz countertops, glass-front upper cabinetry, and matching appliances, flowing seamlessly into the main living area. Three generously sized bedrooms and three full baths include two primary suites—one on the main level and one upstairs—each with its own ensuite, offering ideal separation for guests or extended stays. A third guest bedroom also enjoys a private bath, while an in-unit washer and dryer adds everyday convenience. The screened lanai feels like your own private perch above Pine Island Sound, where it’s just you, the water, and the rhythm of nature. From both the kitchen and lanai, morning sunrises unfold over the Sound, setting the tone for slow mornings, passing wildlife, and uninterrupted calm. Set within South Seas Island Resort in the desirable Bayside Villas enclave, just a stone’s throw from the sugar-white Gulf beaches, the Village of Captiva, and Captiva Landing. Residents and guests enjoy a bayside pool and spa with generous lounging areas, along with under-building parking for added ease. Where time slows, views remain untouched, and every return feels like coming home—this is Captiva at its finest. 3 Beds ⋅ 3 Baths ⋅ 2026017261 MLS Highly sought-after, updated 3 bed, 3 bath two-story villa stands apart with rare features not found in other Bayside units, overlooking the tranquil waters of Pine Island Sound, where unchanging estuary views and native wildlife create a peaceful, elevated backdrop—just moments from the best of Captiva Island. Rare features of this top-floor unit include a walk-in pantry—an uncommon luxury in Bayside 3-bedroom villas—all-new hurricane-impact windows and sliders, and a residence that has been gently used as a private second home and never enrolled in a rental program—an added advantage in condition and care. Whether enjoyed as a private island retreat or leveraged as a high-performing investment, this residence offers rare flexibility within a renter-friendly community and stands as one of the least expensive 3-bedroom opportunities on Captiva. The interior is anchored by an updated kitchen with quartz countertops, glass-front upper cabinetry, and matching appliances, flowing seamlessly into the main living area. Three generously sized bedrooms and three full baths include two primary suites—one on the main level and one upstairs—each with its own ensuite, offering ideal separation for guests or extended stays. A third guest bedroom also enjoys a private bath, while an in-unit washer and dryer adds everyday convenience. The screened lanai feels like your own private perch above Pine Island Sound, where it’s just you, the water, and the rhythm of nature. From both the kitchen and lanai, morning sunrises unfold over the Sound, setting the tone for slow mornings, passing wildlife, and uninterrupted calm. Set within South Seas Island Resort in the desirable Bayside Villas enclave, just a stone’s throw from the sugar-white Gulf beaches, the Village of Captiva, and Captiva Landing. Residents and guests enjoy a bayside pool and spa with generous lounging areas, along with under-building parking for added ease. Where time slows, views remain untouched, and every return feels like coming home—this is Captiva at its finest. 5323 Bayside Villas Unit 24, Captiva
$549,000 Just renovated Bayside Villa located in the gated private South Seas Resort. New kitchen and bathrooms to include granite countertops, shaker cabinets, new flooring, gorgeous walk-in shower all set in a soothing sea salt palette. Wake up to sunrise over Pine Island Sound. The Bayside amenities include an oversized sun-drenched pool and spa, under building parking, on site laundry, pool baths, marina side grills and picnic areas. No rental commitments so all options open. Move in and enjoy or place your property in a rental program. Just footsteps to the beach for a dip in the Gulf of Mexico. Easy access to village of Captiva's shops, restaurants, boating and water sports. Enjoy South Seas world class amenities with membership. Immerse yourself in the luxury of this stunning property. This exclusive opportunity enhances your living experience, offering a range of premium amenities and services tailored for members and guests. With this exceptional membership, enjoy unparalleled access to facilities that elevate your lifestyle. 1 Beds ⋅ 2 Baths ⋅ 2026002394 MLS Just renovated Bayside Villa located in the gated private South Seas Resort. New kitchen and bathrooms to include granite countertops, shaker cabinets, new flooring, gorgeous walk-in shower all set in a soothing sea salt palette. Wake up to sunrise over Pine Island Sound. The Bayside amenities include an oversized sun-drenched pool and spa, under building parking, on site laundry, pool baths, marina side grills and picnic areas. No rental commitments so all options open. Move in and enjoy or place your property in a rental program. Just footsteps to the beach for a dip in the Gulf of Mexico. Easy access to village of Captiva's shops, restaurants, boating and water sports. Enjoy South Seas world class amenities with membership. Immerse yourself in the luxury of this stunning property. This exclusive opportunity enhances your living experience, offering a range of premium amenities and services tailored for members and guests. With this exceptional membership, enjoy unparalleled access to facilities that elevate your lifestyle. 5122 Bayside Villas, Captiva
$150,000 Build Your Private Island Dream Home --- Escape to paradise on exclusive Upper Captiva Island, where this remarkable piece of land offers the best of both worlds—beach and bay access. Nestled between the pristine shoreline of the Gulf of Mexico and the tranquil waters of Foster’s Bay, this lot is the ideal canvas for your dream island retreat. Surrounded by lush tropical foliage and located in a peaceful, car-free community, this property offers ultimate privacy and a true sense of seclusion. Whether you're seeking a luxurious second home or a one-of-a-kind vacation getaway, you’ll enjoy the rare combination of direct beach access for sun-soaked days and convenient bay access for paddleboarding, kayaking, and boating adventures. With no cars, no crowds, and unmatched natural beauty, Upper Captiva is a hidden gem where time slows down. This is your opportunity to create a custom island home in one of Florida’s most remote and magical settings. More pictures will be available at a later date 225056927 MLS Build Your Private Island Dream Home --- Escape to paradise on exclusive Upper Captiva Island, where this remarkable piece of land offers the best of both worlds—beach and bay access. Nestled between the pristine shoreline of the Gulf of Mexico and the tranquil waters of Foster’s Bay, this lot is the ideal canvas for your dream island retreat. Surrounded by lush tropical foliage and located in a peaceful, car-free community, this property offers ultimate privacy and a true sense of seclusion. Whether you're seeking a luxurious second home or a one-of-a-kind vacation getaway, you’ll enjoy the rare combination of direct beach access for sun-soaked days and convenient bay access for paddleboarding, kayaking, and boating adventures. With no cars, no crowds, and unmatched natural beauty, Upper Captiva is a hidden gem where time slows down. This is your opportunity to create a custom island home in one of Florida’s most remote and magical settings. More pictures will be available at a later date Captiva
$12,000,000 One of the Best waterfront properties on the West Coast of Florida. Gulf to Bay, Sunrise to Sunset, 125 feet of Incredible Water Frontage on the Tween Waters stretch on Captlva Island, Florida. Build your Masterpiece here located at One of the highest point elevations on Captlva Island. Located at the mouth of the Bay & Roosevelt Channel. This property enjoys Deep Water Yacht Access & One of the Best covered boat house, lift & dock set ups you will find. In addition to the lot, a full set of the Masterful Work of Art fully completed blue prints by Nationally known Architect John Cooney of Naples (of what could be built) are available for purchase. This property Is a One of A Kind! 225009365 MLS One of the Best waterfront properties on the West Coast of Florida. Gulf to Bay, Sunrise to Sunset, 125 feet of Incredible Water Frontage on the Tween Waters stretch on Captlva Island, Florida. Build your Masterpiece here located at One of the highest point elevations on Captlva Island. Located at the mouth of the Bay & Roosevelt Channel. This property enjoys Deep Water Yacht Access & One of the Best covered boat house, lift & dock set ups you will find. In addition to the lot, a full set of the Masterful Work of Art fully completed blue prints by Nationally known Architect John Cooney of Naples (of what could be built) are available for purchase. This property Is a One of A Kind! 15819 Captiva Drive, Captiva
$4,800,000 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