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.

Real Estate Statistics

Total Listings: 22
Average Price: $3,567,684
Highest Price: $15,500,000
Lowest Price: $150,000

DiscoverCaptiva Island Homes For Sale

22 Properties Found. Showing Page 1 of 3

15819 Captiva Drive W

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 Captiva Island, Florida. On...

16151 Captiva Drive

Captiva, Fl 33924

$13,875,000

  • 6 Beds
  • 7 Full Baths
  • 1 Half Baths
  • 6,737 SqFt

Welcome To Banyan Beach, One Of The Most Beautiful Beach Estates In Sw Florida! As The Epitome Of Luxury Waterfront Living On Captiva Island, This Custom New Construction Estate Is Located On An A...

16512 Captiva Drive

Captiva, Fl 33924

$11,995,000

  • 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...

16611 Captiva Drive

Captiva, Fl 33924

$7,850,000

  • 6 Beds
  • 6 Full Baths
  • 4,900 SqFt

An Incredible Spanish Colonial Revival Waterfront Estate W/roughly 2 Acres Of Natural Island Landscape Directly Across The Street From Golf Cart Accessible Deeded Beach Access. A Fisherman's Parad...

15160 Captiva Drive

Captiva, Fl 33924

$5,249,000

  • 6 Beds
  • 6 Full Baths
  • 1 Half Baths
  • 4,857 SqFt

Stunning Sand Castle! A Towering 6 Bedroom + Den / 6.5 Bathroom Reverse Floor Plan Home That Sprawls Over 4500sq Ft With Multi-level Decks And Bay Views!! Sand Castle Is A Coastal Tuscan Home That...

11516 Wightman Lane

Captiva, Fl 33924

$3,999,000

  • 5 Beds
  • 4 Full Baths
  • 1 Half Baths
  • 3,744 SqFt

A Haven From The Rebuilding Elsewhere On The Island, This Immaculate Fortress Stands As A Testament To The Strength Of New Construction. Infused With A Ubiquitous Style Reflecting Influences From ...

16163 Captiva Drive

Captiva, Fl 33924

$3,995,000

  • 3 Beds
  • 2 Full Baths
  • 1,652 SqFt

This Meticulously Maintained Vintage Captiva Cottage Suffered No Damage From Hurrciane Ian. The Charming & Inviting Cottege Features Your Own Private Beach Access Just A Short Walk From The Home. ...

11529 Andy Rosse Lane

Captiva, Fl 33924

$3,990,050

  • 4 Beds
  • 4 Full Baths
  • 2,636 SqFt

Captiva’s Village By The Sea!! An Old Florida Style 4 Bedroom With Additional Sleeping And Living Areas, 4 Bathroom Home Located In The Heart Of Captiva! Arrive Through The Lush Landscaping And Up...

1 Sunset Captiva Lane

Captiva, Fl 33924

$3,900,000

  • 2 Beds
  • 2 Full Baths
  • 1 Half Baths
  • 1,680 SqFt

Tucked Amidst Swaying Palm Trees Directly On Captiva Island’s World-famous Beach, You’ll Find This Stunning Gulf-front Home. The Gorgeous Interior Paints An Idyllic Setting Only Surpassed By The A...

1650 Lands End Village

Captiva, Fl 33924

$2,590,000

  • 3 Beds
  • 3 Full Baths
  • 2,115 SqFt

Rare Opportunity To Transform This 3 Bedroom, 3 Bath Land's End Village Condominium To Your Own Design! Private Location With Beautiful Views To The Gulf Of Mexico. The Location Provides A Private...



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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