Captiva, FL Homes for Sale with Pool

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  /100

  $3,949,999

  $450K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,630 Sq Ft

  211 Kingfisher Dr, Captiva, FL 33924

  Not everyone can get here... and that’s exactly the point. Indiana Jones Adventure Meets Luxury Island Living | Rare Fly-In / Boat-In Captiva Estate. Set along the waters 300 feet of private white sandy beach & Gulf of America, this extraordinary Upper Captiva property offers one of the most unique lifestyles in Southwest Florida. Located on approximately 1.16 acres, this private island retreat

  

  Jodi Kaplan

  COLDWELL BANKER REALTY

  211 Kingfisher Dr, Captiva, FL 33924
• Explore Captiva

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  /50

  $18,900,000

  • 6 Beds
  • 7 Baths
  • 8,596 Sq Ft

  16950 Captiva Dr, Captiva, FL 33924

  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

  

  Jeff Burns

  Premier Sotheby's Int'l Realty

  16950 Captiva Dr, Captiva, FL 33924
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  /50

  $6,995,000

  $495K PRICE DROP

  • 6 Beds
  • 4.5 Baths
  • 4,624 Sq Ft

  17201 Captiva Dr, Captiva, FL 33924

  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.

  

  Jeff Burns

  Premier Sotheby's Int'l Realty

  17201 Captiva Dr, Captiva, FL 33924
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  /30

  $1,650,000

  $200K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft

  11510 Murmond Ln, Captiva, FL 33924

  Over the years, one of the most popular weekly vacation rental homes on Captiva has had an exceptional rating by VRBO guests. 2026 advance rentals are already over $100,000. This classic Captiva cottage-style home is totally updated with new LVP flooring, two new baths, new quartz kitchen with new S/S appliances, and a separate laundry room. The home is very well furnished for guest comfort with

  

  Larry Hahn

  Berkshire Hathaway Florida

  11510 Murmond Ln, Captiva, FL 33924
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  /41

  $1,099,000

  $176K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,397 Sq Ft

  1659 Lands End Village, Captiva, FL 33924

  At the northernmost tip of Captiva Island, where the turquoise waters of Redfish Pass flow gracefully between the Intracoastal Waterway and the shimmering Gulf of Mexico, awaits one of Florida’s most coveted enclaves. Tucked behind the private gates of the world-renowned South Seas Resort lies Land’s End Village, an intimate retreat of just 17 buildings, each thoughtfully designed with only four

  

  Jeff Burns

  Premier Sotheby's Int'l Realty

  1659 Lands End Village, Captiva, FL 33924
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  /31

  $1,790,000

  $360K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,521 Sq Ft

  11506 Wightman Ln, Captiva, FL 33924

  The popularity of this 3/3 Key West-style home, the Sun & Moon, may place it in the top tier of Captiva rental houses, with over 100 VRBO guests rating it exceptional. It is easy to maintain and prepare for incoming guests. Early 2026 advance reservations already total over $80,000. The house is very well furnished and equipped for guest or owner's use. The metal roof was replaced in 2020.

  

  Larry Hahn

  Berkshire Hathaway Florida

  11506 Wightman Ln, Captiva, FL 33924
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  /43

  $1,099,000

  $176K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,397 Sq Ft

  1659 Lands End Village Unit 1659, Captiva, FL 33924

  At the northernmost tip of Captiva Island, where the turquoise waters of Redfish Pass flow gracefully between the Intracoastal Waterway and the shimmering Gulf of Mexico, awaits one of Florida’s most coveted enclaves. Tucked behind the private gates of the world-renowned South Seas Resort lies Land’s End Village, an intimate retreat of just 17 buildings, each thoughtfully designed with only four

  

  Jeff Burns

  Premier Sotheby's Int'l Realty

  1659 Lands End Village Unit 1659, Captiva, FL 33924
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  /50

  $4,995,000

  • 6 Beds
  • 6.5 Baths
  • 3,092 Sq Ft

  11516 Andy Rosse Ln, Captiva, FL 33924

  Xanadu is a rare expression of contemporary coastal architecture in the heart of Captiva's historic Village. Completely reimagined and rebuilt from the concrete structure up following its 2024 acquisition, every element is new, from the impact windows, Hardie siding and stucco exterior to every interior finish, mechanical system and luxury amenity. On iconic Andy Rosse Lane, Captiva's most

  

  Jeff Burns

  Premier Sotheby's Int'l Realty

  11516 Andy Rosse Ln, Captiva, FL 33924
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  /47

  $5,250,000

  $1M PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,897 Sq Ft

  15899 Captiva Dr, Captiva, FL 33924

  Nestled between the Gulf and Bay, this stunning beachfront home offers unparalleled 180-degree views of both pristine waters, coupled with direct deep-water boating access and a private dock space with lift. Perfect for those who enjoy both the beach and boating lifestyle, this residence seamlessly blends luxurious indoor spaces with expansive outdoor living areas. The thoughtfully designed split

  Michael McMurray Royal Shell Real Estate, Inc.

  15899 Captiva Dr, Captiva, FL 33924
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  /48

  $4,890,000

  $110K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,414 Sq Ft

  15153 Captiva Dr, Captiva, FL 33924

  Wake up to this every day... Captiva's Best Value for Buyers Seeking Walkability, Deep-Water Boating, and the Authentic Island Lifestyle. Imagine beginning each morning with coffee overlooking the sparkling waters of Pine Island Sound as dolphins glide past your private dock and pelicans soar overhead. This is more than a waterfront home—it's a lifestyle that few properties can offer. Perfectly

  Stephanie Bissett Premier Sotheby's Int'l Realty

  15153 Captiva Dr, Captiva, FL 33924
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  /50

  $595,000

  • 2 Beds
  • 2 Baths
  • 894 Sq Ft

  3233 Captiva Resort Villas Unit 3233, Captiva, FL 33924

  Tucked within the gated setting of South Seas Resort, 3233 Tennis Villas presents an inviting island escape in the intimate Captiva Resort Villas community. Residents enjoy access to a private pool, expansive sun deck, gazebo with outdoor dining space, and grilling area, all just moments from the Gulf shoreline. Positioned in the desirable southern enclave and only a short stroll to the beach,

  LeAne Suarez John R. Wood Properties

  3233 Captiva Resort Villas Unit 3233, Captiva, FL 33924
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  Price To Be Determined

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,780 Sq Ft

  Osprey Plan, Captiva, FL 33924

  5400 Plantation Rd Unit 41455767, Captiva, FL 33924
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  /35

  $1,900,000

  • 2 Beds
  • 2 Baths
  • 1,203 Sq Ft

  2122 Gulf Beach Villas Unit 2122, Captiva, FL 33924

  Experience refined Gulf-front living in this exquisite 2-bedroom plus loft, 2-bath, two-story residence at South Seas Resort. Set along the pristine shoreline, this beautifully reconfigured condo blends modern elegance with the relaxed charm of beachfront living. Thoughtful enhancements include plank porcelain flooring, a tankless hot water heater, and a whole-home water filtration system, adding

  LeAne Suarez John R. Wood Properties

  2122 Gulf Beach Villas Unit 2122, Captiva, FL 33924
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  $1,375,000

  $100K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  11400 Old Lodge Ln Unit 1C, Captiva, FL 33924

  Spectacular, direct Bayfront vistas from this furnished, 2 bedroom and 2 bath condo situated in Captiva's "Village" at Captiva Hide-A-Way. “Boater’s Paradise” - dock your boat right out your back door for easy access to Pine Island Sound and the Gulf. Experience magical sun and moon rises from your private lanai and stunning sunsets from the Gulf beach. Conveniently located close to the marina

  Karen Bell Michael Saunders & Company

  11400 Old Lodge Ln Unit 1C, Captiva, FL 33924
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  Price To Be Determined

  New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,346 Sq Ft

  Egret Plan, Captiva, FL 33924

  5400 Plantation Rd Unit 41455782, Captiva, FL 33924
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  /47

  $1,500,000

  • 3 Beds
  • 2 Baths
  • 1,034 Sq Ft

  2030 Gulf Beach Villas Unit 2030, Captiva, FL 33924

  Located on the stunning beaches of South Seas Resort, this exceptional 3-bedroom, 2-bathroom Gulf Beach Villa has been completely renovated to offer a premier seaside sanctuary living experience. Situated in one of the most sought-after Gulf-front locations on Captiva, this lovely condominium provides not only an upscale coastal oasis but also a fantastic rental income opportunity. Inside, you'll

  Mary Ann Cowart Royal Shell Real Estate, Inc.

  2030 Gulf Beach Villas Unit 2030, Captiva, FL 33924
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  /49

  $3,695,000

  • 4 Beds
  • 4 Baths
  • 1,618 Sq Ft

  25 Beach Homes, Captiva, FL 33924

  Located within the gates of South Seas Resort on Captiva Island, Beach Home 25 has been completely reimagined into a refined 4 bedroom, 4 bath coastal retreat that captures the essence of island living. With sweeping Gulf views from multiple vantage points and direct access to what are widely regarded as some of the most pristine and natural beaches in the United States, this residence offers a

  LeAne Suarez John R. Wood Properties

  25 Beach Homes, Captiva, FL 33924
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  /49

  $1,895,000

  $100K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,115 Sq Ft

  1656 Lands End Village Unit 1656, Captiva, FL 33924

  Seller Incentive: $50,000 Credit at Closing — Purchaser to receive a $50,000 credit at closing, providing flexibility to personalize, update, furnish, or enhance the residence to suit their preferences. A rare opportunity to acquire this exceptional Lands' End residence with additional flexibility to customize finishes, make improvements, or create your ideal Captiva retreat. This exceptional

  Jerry Burden Timbers FL Real Estate Company LLC

  1656 Lands End Village Unit 1656, Captiva, FL 33924
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  /49

  $4,900,000

  • 3 Beds
  • 3 Baths
  • 2,096 Sq Ft

  19 Beach Homes, Captiva, FL 33924

  Offering a premier direct Gulf-front location, Beach Home 19 is an elevated 3 Bedroom + Den, 3 Bath residence positioned along one of Captiva’s most sought-after stretches of beach within the gates of South Seas. Thoughtfully redesigned and extensively renovated, this exceptional home blends modern coastal sophistication with the natural beauty of its beachfront setting. The open-concept interior

  LeAne Suarez John R. Wood Properties

  19 Beach Homes, Captiva, FL 33924
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  /50

  $475,000

  $24K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 954 Sq Ft

  370 Townhouse Ln Unit 60, Captiva, FL 33924

  End Unit With Harbor Views & Dock Access! Experience the tropical island waterfront lifestyle! This value-priced townhome offers shared dockage for your boat, and an unbeatable location just steps from the dockage, ferry landing, and club restaurant... because sometimes the outside is doing all the heavy lifting. Let’s be clear: the interior is authentically, unapologetically vintage. We’re

  Mark Muller Resort Properties Internationa

  370 Townhouse Ln Unit 60, Captiva, FL 33924
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  /50

  $595,000

  • 2 Beds
  • 2 Baths
  • 894 Sq Ft

  3233 Captiva Resort Villas, Captiva, FL 33924

  Tucked within the gated setting of South Seas Resort, 3233 Tennis Villas presents an inviting island escape in the intimate Captiva Resort Villascommunity. Residents enjoy access to a private pool, expansive sun deck, gazebo with outdoor dining space, and grilling area, all just moments from the Gulfshoreline. Positioned in the desirable southern enclave and only a short stroll to the beach, this

  LeAne Suarez John R. Wood Properties

  3233 Captiva Resort Villas, Captiva, FL 33924
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  /41

  $1,049,000

  $426K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,500 Sq Ft

  2121 Gulf Beach Villas, Captiva, FL 33924

  This two-story, three-bedroom, three-bath Beach Villa offers direct Gulf views and a desirable corner location that enhances privacy and natural light—an ideal combination for both personal enjoyment and rental appeal. The open-concept living, dining, and kitchen areas create a comfortable coastal setting well-suited for entertaining or unwinding after a day on the beach. Enjoy the sound of the

  LeAne Suarez John R. Wood Properties

  2121 Gulf Beach Villas, Captiva, FL 33924
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  /45

  $7,950,000

  $4M PRICE DROP

  • 6 Beds
  • 5.5 Baths
  • 5,813 Sq Ft

  16512 Captiva Dr, Captiva, FL 33924

  Nestled along Captiva Island’s most coveted stretch of the Gold Coast, this exceptional beachfront private estate is surrounded by lush tropical landscaping, offering the ultimate blend of serenity and sophistication. Behind its unassuming beach house exterior lies a strikingly modern, European-inspired interior that radiates style and comfort. The main residence and guest house combine to offer

  Michael McMurray Royal Shell Real Estate, Inc.

  16512 Captiva Dr, Captiva, FL 33924
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  /50

  $10,900,000

  • 5 Beds
  • 5.5 Baths
  • 5,059 Sq Ft

  16730 Captiva Dr, Captiva, FL 33924

  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

  Michael McMurray Royal Shell Real Estate, Inc.

  16730 Captiva Dr, Captiva, FL 33924
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  /46

  $549,000

  • 1 Bed
  • 2 Baths
  • 684 Sq Ft

  5122 Bayside Villas Unit 5122, Captiva, FL 33924

  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,

  Joan Stokes Timbers FL Real Estate Company LLC

  5122 Bayside Villas Unit 5122, Captiva, FL 33924
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  Price To Be Determined

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 2,894 Sq Ft

  Crane Plan, Captiva, FL 33924

  5400 Plantation Rd Unit 41455777, Captiva, FL 33924
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  /50

  $2,795,000

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft

  3 Beach Homes, Captiva, FL 33924

  A rare opportunity to own a classic three-bedroom beach home in South Seas Resort, perfectly positioned to capture sweeping views of the Gulf beach, pool and Captiva's spectacular nightly sunsets. Wake up to views of the beach from the primary bedroom, gather with family and friends in the vaulted living room, and end the day on the spacious screened lanai as another unforgettable Captiva sunset

  Lamar Stokes Timbers FL Real Estate Company LLC

  3 Beach Homes, Captiva, FL 33924
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  $11,500,000

  • 7 Beds
  • 7.5 Baths
  • 7,093 Sq Ft

  17030 Captiva Dr, Captiva, FL 33924

  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 –

  Donald Deluca Royal Shell Real Estate, Inc.

  17030 Captiva Dr, Captiva, FL 33924
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  /50

  $4,495,000

  $295K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 2,680 Sq Ft

  27 Beach Homes, Captiva, FL 33924

  Picture yourself on island time where contemporary coastal elegance meets the pristine shores of Captiva Island. This 5 bedroom, 4 1/2 bath gem represents the thoughtfully reimagined collaborative vision of Amy Nowacki's architectural expertise, Will Smith's masterful construction, and Aniko's inspired interior design—creating a space that's as refined as it is relaxed. Step inside where every

  Lamar Stokes Timbers FL Real Estate Company LLC

  27 Beach Homes, Captiva, FL 33924
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  /50

  $1,245,000

  • 3 Beds
  • 2.5 Baths
  • 1,243 Sq Ft

  543 Gulf Ln, Captiva, FL 33924

  Island Paradise Found: Gulf-Side Retreat with Private Hot Tub/Pool & Tiki Bar! Wake up to your dream beach paradise on North Captiva Island! This exceptionally well-maintained 3-bedroom, 2.5-bath 1/2 duplex oasis offers unbeatable views and amenities designed for luxurious island life. Step inside to an open-concept living area featuring vaulted ceilings, bright coastal décor, a spacious kitchen

  Mark Muller Resort Properties Internationa

  543 Gulf Ln, Captiva, FL 33924
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  /50

  $1,999,000

  • 4 Beds
  • 3 Baths
  • 2,197 Sq Ft

  150 White Pelican Dr, Captiva, FL 33924

  Expansive & Panoramic Gulf Views with the Beach Just Steps Away! This soaring 4 bedroom and 3 bath estate home offers Hardie board siding, aluminum railings, and impact windows. The reverse floorplan creates fantastic views from every corner of the living spaces, indoors and out. Imagine relaxing on the 2nd level porch or 3rd-floor mezzanine, gazing at the incredibly scenic coastline of Cayo

  Mark Muller Resort Properties Internationa

  150 White Pelican Dr, Captiva, FL 33924
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  /41

  $735,000

  • 2 Beds
  • 2 Baths
  • 861 Sq Ft

  802 Marina Villas Unit 802, Captiva, FL 33924

  Wake each morning to panoramic yacht harbor views and the gentle rhythm of island life from this updated waterfront retreat in Marina Villas, where Captiva's sugar-sand beaches and the sparkling Gulf of Mexico are just a short stroll away. Ideally positioned on the quiet north end of South Seas Island Resort, this furnished residence overlooks the yacht harbor and navigable channel, offering a

  Mary Ann Cowart Royal Shell Real Estate, Inc.

  802 Marina Villas Unit 802, Captiva, FL 33924
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  /44

  $1,845,000

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,776 Sq Ft

  33 Urchin Ct, Captiva, FL 33924

  Welcome to Sunset Captiva, one of Captiva Island's most sought-after Gulf-to-Bay communities, ideally located in the heart of Captiva's charming Village. This beautifully updated 3 bed, 2 bath island retreat offers the perfect combination of coastal elegance, modern upgrades, and the relaxed island lifestyle that makes Sunset Captiva so desirable. Step inside to discover an open, light-filled

  LeAne Suarez John R. Wood Properties

  33 Urchin Ct, Captiva, FL 33924
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  /46

  $9,450,000

  • 6 Beds
  • 6.5 Baths
  • 5,346 Sq Ft

  16777 Captiva Dr, Captiva, FL 33924

  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

  Phaidra McDermott Kingfisher Real Estate Inc.

  16777 Captiva Dr, Captiva, FL 33924
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  /50

  $9,700,000

  • 5 Beds
  • 4.5 Baths
  • 4,134 Sq Ft

  16770 Captiva Dr, Captiva, FL 33924

  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

  LeAne Suarez John R. Wood Properties

  16770 Captiva Dr, Captiva, FL 33924
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  /42

  $1,395,000

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,132 Sq Ft

  2236 Beach Villas Unit 2236, Captiva, FL 33924

  Escape to your own slice of paradise at the Sunset Beach Villas, where Gulf breezes whisper through swaying palms and every sunset paints the sky in brilliant hues just beyond your screened lanai. This thoughtfully redesigned three-bedroom, two-bathroom condo spans 1,132 square feet of coastal comfort, offering an intimate retreat that sleeps eight. The modified floorplan flows seamlessly from

  Lamar Stokes Timbers FL Real Estate Company LLC

  2236 Beach Villas Unit 2236, Captiva, FL 33924
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  /35

  $510,000

  $90K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 989 Sq Ft

  370 Townhouse Ln, Captiva, FL 33924

  Steps from the water! You can hear the bay waters gently sloshing against the shoreline from the front deck. Enjoy beautiful bay views from the front screened-in deck and watch the boats come and go from Safety Harbor. Relax to the sounds of the cheerful sea birds that soar over Safety Harbor and watch the dolphins swim in the bay. This meticulously maintained townhouse has gorgeous views of

  Desiree Wilson Preferred Properties Group Inc

  370 Townhouse Ln, Captiva, FL 33924
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  /38

  $5,699,000

  $251K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 3,681 Sq Ft

  16632 Captiva Dr, Captiva, FL 33924

  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.

  Sue Plein Kingfisher Real Estate, Inc.

  16632 Captiva Dr, Captiva, FL 33924
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  /44

  $549,000

  • 1 Bed
  • 2 Baths
  • 684 Sq Ft

  5122 Bayside Villas, Captiva, FL 33924

  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,

  Joan Stokes Timbers FL Real Estate Company

  5122 Bayside Villas, Captiva, FL 33924
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  /50

  $3,250,000

  $250K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 2,115 Sq Ft

  4620 Oro Pesos Ln, Captiva, FL 33924

  Gulf-front luxury living on the pristine beaches of North Captiva Island, offering a rare two-lot homesite with sweeping panoramic views of the Gulf of America, Captiva Pass, and Cayo Costa Island, where unforgettable sunsets unfold nightly. Thoughtfully designed for comfort, resilience, and effortless island living, this exceptional residence features a whole-house reverse osmosis system,

  Jeff Miloff The Keyes Company

  4620 Oro Pesos Ln, Captiva, FL 33924

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