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: 63
Average Price: $3,766,816
Highest Price: $26,985,000
Lowest Price: $109,000

DiscoverCaptiva Island Homes For Sale

63 Properties Found. Showing Page 1 of 7

16486/488 Captiva Drive

Captiva, Fl 33924

$26,985,000

  • 6 Beds
  • 11 Full Baths
  • 2 Half Baths
  • 12,284 SqFt

This Is A “once In A Lifetime” Offering Of Over 6 Acres Of Prime Waterfront Property! A Spectacular Gated Estate Nestled On Captiva’s Prestigious Gold Coast. This Family Compound Stretches From Th...

0 Buck Key

Captiva, Fl 33924

$21,000,000

One Of North America’s Last Remaining Buildable Islands, Buck Key Is A Pristine Uninhabited Tropical Island Consisting Of 350 Acres Of Federal Preserve And Stunning Water Frontage Along The Roosev...

15819 Captiva Drive

Captiva, Fl 33924

$15,500,000

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. On...

11531 Paige Court

Captiva, Fl 33924

$12,995,000

  • 4 Beds
  • 3 Full Baths
  • 1 Half Baths
  • 3,691 SqFt

Welcome To ‘stay Salty’ Where Panoramic Gulf To Bay Vistas Await! Nestled Within The Exclusive Gated Community Of Tarpon Bay, This Property Offers Unparalleled Views In The Heart Of Captiva. Desig...

16280 Captiva Drive

Captiva, Fl 33924

$12,000,000

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 ...

Photo of 16512 Captiva Drive, CAPTIVA FL

16512 Captiva Drive

Captiva, Fl 33924

$10,500,000

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

Nestled W/in A Lush Tropical Estate Setting & Located Along The Best Stretch Of The Gold Coast Of Captiva Island Is This Fantastic Beachfront Private Estate. The Home Offers An Unassuming Beach Ho...

16770 Captiva Drive

Captiva, Fl 33924

$9,900,000

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

South Haven, 16770 Captiva Dr. A Meticulously Crafted Estate Showcases A Timeline Of Enhancements, Blending Opulence With Functionality. Noteworthy Features Include A Remodeled, Kitchen And Dini...

16979 Captiva Drive

Captiva, Fl 33924

$9,250,000

  • 6 Beds
  • 7 Full Baths
  • 1 Half Baths
  • 5,598 SqFt

One Of Captiva's Most Iconic Residences Resting On Over 2.5 Acres With 200 Ft Of Bay-frontage Overlooking The Sparkling Waters Toward The Preservation Land Beyond. Situated On A Peninsula This Pro...

14971 Binder Drive

Captiva, Fl 33924

$8,500,000

  • 4 Beds
  • 3 Full Baths
  • 3,367 SqFt

Discover Coastal Luxury On Captiva Island, Where This Prestigious Bayfront Estate Has Been The Talk Of The Town For Over Three Decades. Perfectly Positioned In The Quaint Village Of Captiva, Every...

16632 Captiva Drive

Captiva, Fl 33924

$7,950,000

  • 5 Beds
  • 4 Full Baths
  • 3,681 SqFt

16632 Captiva Drive - Step Into "halemakai," The Coastal Haven On Captiva’s Gold Coast! With A Generous 100 Feet Of Gulf Frontage, This Residence Emanates Coastal Allure And Indigenous Relaxation....



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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