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: 18
Average Price: $3,086,356
Highest Price: $18,900,000
Lowest Price: $250,000

DiscoverCaptiva Island Homes For Sale

18 Properties Found. Showing Page 1 of 2
Photo of 16950 Captiva Drive, Captiva FL

16950 Captiva Drive

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...

16770 Captiva Drive

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,...

Photo of 16500 Captiva Drive, Captiva FL

16500 Captiva Drive

Captiva, Fl 33924

$6,750,000

  • 6 Beds
  • 6 Full Baths
  • 1 Half Baths
  • 4,000 SqFt

Welcome To A Stunning Coastal-modern Beachfront Estate On Captiva Island’s Exclusive Gold Coast. This Beautifully Enhanced Home Combines Comfort, Nature, And Luxury Across More Than 100 Feet Of Pr...

Photo of 16475 Captiva Drive, Captiva FL

16475 Captiva Drive

Captiva, Fl 33924

$4,995,000

  • 3 Beds
  • 3 Full Baths
  • 1 Half Baths
  • 3,258 SqFt

Presented With A New Design Vision By Mhk Architecture, This Extraordinary Captiva Island Estate Features Concept Plans To Reimagine The Existing Residence, Design A New Coastal Masterpiece, Or Ex...

16979 Captiva Drive

Captiva, Fl 33924

$4,900,000

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

This Is A Short Sale! Deeded Beach Access! Opportunity Is Knocking! Answer The Door! One Of Captiva's Most Iconic Residences Resting On Over 2.5 Acres With 200 Ft Of Bay-frontage Overlooking The ...

1606 Lands End Village

Captiva, Fl 33924

$2,600,000

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

Excellent Opportunity To Own A Premier Location At Lands End. The Views Overlooking The Bay And Pine Island Sound Are Simply Amazing! Beautifully Furnished! Gorgeous Kitchen And Bathrooms. Reconfi...

Photo of 131 Kingfisher Drive, Captiva FL

131 Kingfisher Drive

Captiva, Fl 33924

$1,495,000

  • 2 Beds
  • 1 Full Baths
  • 1,176 SqFt

Rare Bayfront Fixer Upper!  impressive Panoramic Big Water Views Combine with A private sandy Bayside Beach And the Best island Fishing right From Your dock. this Tropical Retreat Features Vaulted...

1655 Lands End Village

Captiva, Fl 33924

$1,250,000

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

Morning Light Floods The Beautiful Window Lined Sunroom Of This Fabulous Condo Creating Spectacular Views Of The Sparkling Lake And Of The Magnificent Sunrise Over Pine Island Sound. Lands End Is ...

Photo of 1659 Lands End Village, Captiva FL

1659 Lands End Village

Captiva, Fl 33924

$1,199,000

  • 2 Beds
  • 2 Full Baths
  • 1,397 SqFt

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 D...

Photo of 310 Pieces Of Eight, Captiva FL

310 Pieces Of Eight

Captiva, Fl 33924

$724,000

  • 2 Beds
  • 3 Full Baths
  • 1,656 SqFt

*updated Listing - A Must Read* Amazing Opportunity! An Island Treasure! Prime Waterfront Home & Commercially Zoned Oversized Parcel Property Of .33 Acres With Direct Gulf Access Frontage And Expa...



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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