Captiva Island

Author Edna St. Vicent Millay, a resident of Captiva Island, poetically penned, “All the loveliest things there be come simply, so it seems to me.” Certainly, the simple beauty of Captiva Island is its most captivating characteristic. A barrier island off the coast of Southwest Florida, Captiva Island shares its shore with sister Sanibel, a slightly more populous island that contains a causeway back to Florida's mainland. The tropical oasis was originally inhabited by the Calusas Indians, a Native American tribe well known for their fishing, hunting, and fighting skills. After the Calusas tribe protected their land from Spanish explorers, they unfortunately fell victim to European diseases and plagues. The region remained untouched until pirates marauded Florida’s barrier islands and “Buccaneer” coastline. In fact, legend insinuates that pirate Jose Gaspar buried his treasure and constructed a prison on “Isle de los Captivas” in the early 1800s where he kept female prisoners captive for ransom. Now known as Captiva Island, the town’s history of Native Americans, Spanish explorers, buccaneers, prolific writers, prominent business inventors, and key lime pie all contribute to the town's storied past and present establishments.

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Real Estate Statistics

Total Listings: 117
Average Price: $2,946,971
Highest Price: $18,900,000
Lowest Price: $114,900

DiscoverCaptiva Island Homes For Sale

117 Properties Found. Showing Page 1 of 12

16950 Captiva Dr

Captiva, Fl 33924

$18,900,000

  • 6 Beds
  • 7 Full Baths
  • 8,596 SqFt

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 Bu...

16530 Captiva Dr

Captiva, Fl 33924

$12,500,000

  • 5 Beds
  • 5 Full Baths
  • 1 Half Baths
  • 5,843 SqFt

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...

16280 Captiva Dr

Captiva, Fl 33924

$12,000,000

  • 2.00 Acres

Discover An Unparalleled Beachfront Jewel On The Prestigious Gold Coast Of Captiva Island. This 2-acre Estate Lot Boasts A Unique 153 Ft Of Pristine Beach Frontage, Uniquely Situated On A Stretch ...

15819 Captiva Dr

Captiva, Fl 33924

$12,000,000

  • 1.20 Acres

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. Bu...

15735/737 Captiva Dr

Captiva, Fl 33924

$11,900,000

  • 5 Beds
  • 5 Full Baths
  • 1 Half Baths
  • 5,751 SqFt

Set Amidst The Glistening Waters Of The Gulf And The Captivating Bay, This Stunning Estate Epitomizes Unparalleled Luxury And Exclusive Waterfront Living. Stretching From Beachside To Bayside, The...

17030 Captiva Dr

Captiva, Fl 33924

$11,500,000

  • 6 Beds
  • 7 Full Baths
  • 1 Half Baths
  • 6,292 SqFt

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 P...

16770 Captiva Dr

Captiva, Fl 33924

$9,700,000

  • 5 Beds
  • 4 Full Baths
  • 1 Half Baths
  • 4,134 SqFt

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,...

$9,450,000

  • 3 Beds
  • 3 Full Baths
  • 1 Half Baths
  • 3,152 SqFt

Rare Opportunity To Purchase A Luxurious Gulf Front Estate On Captiva Island Within The Gated Resort Community Of South Seas. This Stunning, Coastal 5 Bdrm Property Offers 102' Of Beach Frontage ...

16777 Captiva Dr

Captiva, Fl 33924

$9,450,000

  • 6 Beds
  • 6 Full Baths
  • 1 Half Baths
  • 5,346 SqFt

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...

16512 Captiva Dr

Captiva, Fl 33924

$7,950,000

  • 6 Beds
  • 5 Full Baths
  • 1 Half Baths
  • 5,813 SqFt

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 Serenit...



By 1830 the pirates were no longer a threat, and the U.S. government deemed Captiva and Sanibel as safe settlements. In 1923, Clarence Chadwick, who invented overlays for checks to prevent forgeries, purchased the majority of Captiva and planned to retire with his wife, Rosamond, who believed the warm weather would ease Chadwick’s arthritis. Chadwick didn’t retire for long. He built the Manor House and turned the property into a key lime plantation. His plantation soon became the largest producer of key limes in the world. Today, the property is known as South Seas Resort, a spectacular 330-acre property that offers vacation villa rentals, hotel accommodations, and, of course, delicious key lime pie.

Apart from divulging in key lime pie, residents and visitors enjoy relaxing at the beach, shelling at Blind Pass, watching the sunset at Captiva Beach, playing golf, exploring nature, fishing, and spending time with friends and family. The low-key island is laid-back, and its natural wonderment is center stage. Captiva is ideal for those who desire privacy and tranquility.

Real estate on Captiva Island includes beachfront estates, waterfront condos, golf course homes, seaside villas, and cottage-style homes. Presently, Captiva contains 18 individual neighborhoods with single family homes or bungalow style cottages, and 17 low-rise condominiums. Oceanfront properties offer panoramic views of the gentle Gulf of Mexico, and interior homes are within walking distance to the sugary white sand coastline.

Author Anne Morrow Lindbergh wrote her famous novel Gift from the Sea while residing on Captiva Island. In the book, she metaphorically describes the sea’s instruction, writing “The sea does not reward those who are too anxious, too greedy, or too impatient. To dig for treasures shows not only impatience and greed, but lack of faith. Patience, patience, patience is what the sea teaches. Patience and faith. One should lie empty, open, choiceless as a beach — waiting for a gift from the sea.” Certainly, Captiva residents understand and appreciate the sea’s gift: the tropical island itself is the true treasure.

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Charleston Trident Association of Realtors Logo The data relating to real estate for sale on this web site comes in part from the Broker ReciprocitySM Program of the Charleston Trident Multiple Listing Service. Real estate listings held by brokerage firms other than Nicklaus Vance are marked with the Broker ReciprocitySM logo or the Broker ReciprocitySM thumbnail logo (a little black house) and detailed information about them includes the name of the listing brokers.

The broker providing these data believes them to be correct, but advises interested parties to confirm them before relying on them in a purchase decision.

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