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.
127 days on market · Listing updated May 26, 2026
| Date | Event | Price |
|---|---|---|
| Apr 23, 2026 | Original list price | $3,000,000 |
Reflects listing data on file, not a complete transaction history.
Listed by Dawn Marie Ramsey, Pfeifer Realty Group LLC
$3,000,000
4819 Tradewinds DR, SANIBEL
$16,467
est. monthly payment
Estimate only — actual payment depends on your lender, credit profile, and final loan terms.
The data relating to real estate for sale displayed on this Website comes in part from the Multiple Listing Service of the Bonita Springs-Estero Association of REALTORS®, Inc., under License No. BK3468074. Properties displayed on this Website include properties listed with brokerage firms other than Sands Real Estate & Property Management. Detailed information about such properties includes the name of the brokerage firm with which the seller has listed the property. The properties displayed may not be all the properties listed with brokerage firms participating in the Bonita Springs-Estero Association of REALTORS® Multiple Listing Service, or contained in the database compilation of the Bonita Springs-Estero Association of REALTORS® Multiple Listing Service.