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$3,000,000

4819 Tradewinds DR, SANIBEL FL, 33957

Price per sqftN/A
Built in1958
Property typeCommercial
Courtesy of Dawn Marie Ramsey, Pfeifer Realty Group LLC, (239) 233-2976

Overview

Active

Listed Apr 23, 2026

Updated Jun 3

Opportunities like this don’t come along often. Own a prime piece of Sanibel Island; or three! With rare nightly rental zoning, exceptional income potential, and redevelopment already positioned to move forward, the Tropical Winds portfolio represents one of the island’s most unique and valuable investment opportunities. With an architect, engineer, and contractor already assembled and ready to begin immediately, the Tropical Winds portfolio presents a rare opportunity to accelerate redevelopment with a projected opening for the 2027 season if acquired in June. Now cleared and ready for reconstruction, the Tropical Winds portfolio presents a rare opportunity to reimagine multiple income-producing parcels in one of Sanibel’s most exclusive and tightly regulated sectors: nightly rentals. In a market where most properties are limited to 30-day minimum rentals, this offering stands apart with zoning that allows short-term vacation rentals, creating exceptional revenue potential in a highly supply-constrained segment. The portfolio includes a six-unit Gulf-front hotel with direct beach access and sweeping northwestern views of the Gulf of Mexico, along with two duplex properties that also benefit from coveted nightly rental eligibility: 1344 & 1350 Jamaica Drive; Lots zoned for two duplex constructions. Impacted by Hurricane Ian and now cleared, the properties offer a blank canvas for new, elevated construction. Sanibel’s post-Ian Build-Back provisions allow redevelopment within the original building footprint and volume, while enabling modern improvements such as elevated structures, enhanced views, under-building parking, storage, and increased storm resilience. The west-facing hotel site borders protected land, ensuring long-term privacy and unobstructed sunset views; an increasingly rare coastal advantage. This is a unique chance to develop higher-end accommodations while retaining the valuable nightly rental zoning that makes this portfolio truly exceptional.

Additional information

MLS® ID
2026018790

Interior Features

Basement
No

Exterior Features

Lot Size
0.94 Acres

Other Property Details

Taxes
$28,748
Tax Frequency
Annually
Association Fee Frequency
Yearly
Waterfront
Yes
55+/Senior Community
No
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The IDX display contains information sourced from the Naples Area Board of REALTORS® as of 6/3/2026. This data is intended solely for personal, non-commercial use and is not to be utilized for any other purposes except to identify potential properties for purchase. Although the MLS data displayed is typically considered reliable, it is not guaranteed to be accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and are advised to conduct their own investigations or seek professional assistance. Other sources besides the Listing Agent may have contributed to the MLS data presented. Unless expressly specified in writing, the Broker/Agent has not confirmed any information obtained from external sources. The Broker/Agent may or may not have acted as the Listing and/or Selling Agent and cannot guarantee the accuracy of property locations displayed on any map. Any compensation offers are solely made to participants of the MLS where the listing is registered.

©2026 Naples Area Board of REALTORS® All rights reserved.

Data last updated 5:40 PM UTC, 6/3/2026

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