Luxury Homes for Sale in Upper Captiva, FL

The luxury market in Upper Captiva starts at $1,000,000. This page is every active listing at that level, refreshed nightly from the MLS, with what has actually closed, where the inventory sits and how long it takes to sell. For the wider picture see luxury communities in Lee County.

11 luxury homes are for sale in Upper Captiva, FL at $1,000,000 and up — median asking $1,425,000, the top listing at $3,895,000, $848 per square foot. Median days on market: 156.

Newest luxury listings in Upper Captiva

$1,450,000
4 bd · 4 ba · 2,262 sq ft · built 2005
4490 Oyster Shell Dr, 33924
North Captiva Dunes
Listing courtesy of Islander Realty
$1,397,000
3 bd · 2 ba · 1,841 sq ft · built 1982
4490 Harbor Bend Dr, 33924
Safety Harbor Club
Listing courtesy of Resort Properties Internationa
$1,300,000
3 bd · 3 ba · 1,656 sq ft · built 2003
4510 Oyster Shell Dr, 33924
North Captiva Dunes
Listing courtesy of Resort Properties Internationa
$3,250,000
4 bd · 5 ba · 2,115 sq ft · built 2021
4620 Oro Pesos Ln, 33924
Jose'S Hideaway
Listing courtesy of The Keyes Company
$1,499,000
3 bd · 3 ba · 1,808 sq ft · built 2022
4500 Seair Ln, 33924
Jose'S Hideaway
Listing courtesy of Resort Properties Internationa

The most expensive homes for sale in Upper Captiva

ListingAskingSq ft$ / sq ftCommunity
660 Gulf Ln$3,895,0003,340$1,166—
4620 Oro Pesos Ln$3,250,0002,115$1,537Jose'S Hideaway
150 White Pelican Dr$1,999,0002,197$910—
4500 Seair Ln$1,499,0001,808$829Jose'S Hideaway
4490 Oyster Shell Dr$1,450,0002,262$641North Captiva Dunes
4460 Smugglers Dr$1,425,0002,358$604—
4490 Harbor Bend Dr$1,397,0001,841$759Safety Harbor Club
4541 Conch Shell Dr$1,395,0001,646$848—
4510 Oyster Shell Dr$1,300,0001,656$785North Captiva Dunes
543 Gulf Ln$1,245,0001,243$1,002—

Where the luxury inventory is

CommunityLuxury listingsMedian asking
Jose'S Hideaway2$2,374,500
North Captiva Dunes2$1,375,000
Safety Harbor Club1$1,397,000

Luxury inventory by price

BandFor saleShare
$1,000,000–$1,500,000873%
$1,500,000–$2,000,00019%
$3,000,000–$5,000,000218%

How to read this

Luxury is defined here as asking prices at or above $1,000,000. Counts, medians and closings come from active and closed MLS listings as of November 12, 2026; closings are the trailing 12 months. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 6 homes for sale in Upper Captiva and what $1M buys across Lee County.

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Common questions

How many luxury homes are for sale in Upper Captiva?

11 homes are listed at $1,000,000 or more in Upper Captiva, FL as of November 12, 2026, with a median asking price of $1,425,000.

What is the most expensive home for sale in Upper Captiva?

The highest asking price right now is $3,895,000.

Which Upper Captiva communities have the most luxury listings?

Jose'S Hideaway (2), North Captiva Dunes (2), Safety Harbor Club (1).