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: 39
Average Price: $2,967,831
Highest Price: $21,000,000
Lowest Price: $129,900

DiscoverCaptiva Island Homes For Sale

39 Properties Found. Showing Page 1 of 4

0 Buck Key

Captiva, Fl 33924


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...

16512 Captiva Drive

Captiva, Fl 33924


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

Nestled Within 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...

16632 Captiva Drive

Captiva, Fl 33924


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

Welcome To "halemakai", The House Of The Sea On Captiva’s Gold Coast! Boasting 100ft Of Gulf Frontage, This Stunning Property Exudes Coastal Charm And Native Beauty While Offering Multiple Dwellin...

211 Kingfisher Drive

Captiva, Fl 33924


  • 5 Beds
  • 5 Full Baths
  • 3,938 SqFt

Exclusive Island Estate With Spectacular Views Of Pine Island Sound And The Gulf Of Mexico. This 5 Bedroom, 5 Bath Home Is Situated On 1.16 Acres Of Beautifully Landscaped, Irrigated Property With...

11550 Paige Court

Captiva, Fl 33924


  • 5 Beds
  • 4 Full Baths
  • 2 Half Baths
  • 4,129 SqFt

Tucked Quietly Along The Coast Of Captivating Captiva Island, You Will Find The Community Of Tarpon Bay. This Gated Gulf-front Estate Offers Gulf And Bay Living At Its Very Finest, Where You Truly...

15557 Captiva Drive

Captiva, Fl 33924


  • 5 Beds
  • 4 Full Baths
  • 1 Half Baths
  • 3,420 SqFt

This Stunning Bayfront Home On Captiva’s Coveted Tween Water’s Stretch Combines Breathtaking Views Of The Bay With Meticulous Craftmanship And A Wonderful Floorplan. This Five-bedroom Home Greets ...

1101 Tallow Tree Court

Captiva, Fl 33924


  • 4 Beds
  • 4 Full Baths
  • 3,531 SqFt

The Perfect Paradise! Direct Beachfront, At South Seas Island Resort. This 4 Bedroom, 4 Bath Gulf Cottage Offers The Perfect Location For Unexpected Privacy And Is Convenient To Everything The Re...

11505 Gore Lane

Captiva, Fl 33924


  • 6 Beds
  • 6 Full Baths
  • 4,248 SqFt

This Lux Captiva Village Beauty Is Back! Just A Short 6 Minute Stroll To The Aquamarine Waters Of The Gulf. This 6br, 6bath, 2 Car, Heated Pool+spa Home Has Plenty Of Extra Outdoor Lounging Areas,...

16321 Captiva Drive

Captiva, Fl 33924


  • 5 Beds
  • 4 Full Baths
  • 3,522 SqFt

Welcome To Turtle Run! A Stunning Bayfront Property Located On The Picturesque Roosevelt Channel. This Magnificent Estate Offers An Unparalleled Combination Of Serenity, Comfort, And Natural Beaut...

24 Beach Homes

Captiva, Fl 33924


  • 3 Beds
  • 3 Full Baths
  • 2,194 SqFt

Blissful Beach Home 24! Situated Directly On The Gulf Beaches, This 3 Bedroom, 3 Bathroom, Free-standing, Two-story Beach Home Allows One To Experience An Unparalleled Tropical Lifestyle! Hear The...

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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