Ad #7614595
MLS #2026018790
Opportunities like this don't come along often. Own a prime
4819 Tradewinds Dr, Sanibel, FL 33957
$3,000,000
--Beds
--Baths
--Sqft
0.94Acres
About this property
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.
Property Features
0 Beds
0 Baths
0 Sqft
Built in 1958
0.94 Acres
1 Story
On Beachfront
$28,748 / yr property tax
Lee County
Additional Photos
Contact Information
Dawn Marie Ramsey
Pfeifer Realty Group
239-233-2976
Location
Listing Agent: Dawn Marie Ramsey (License #: 280597316) 239-233-2976
Broker: Pfeifer Realty Group 239-472-0004 Listing Site
Copyright © 2026 Florida Gulf Coast Multiple Listing Service, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Broker: Pfeifer Realty Group 239-472-0004 Listing Site
Copyright © 2026 Florida Gulf Coast Multiple Listing Service, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
BeachHouse.com
Printed Aug 12, 2026
Photo Gallery
$3,000,000
--
Beds
--
Baths
--
Sqft
4819 Tradewinds Dr, Sanibel, FL 33957
By contacting this agent you agree to these Terms and Conditions.
MLS# 2026018790
Opportunities like this don't come along often. Own a prime
$3,000,000
4819 Tradewinds Dr, Sanibel, FL 33957
--
Beds
--
Baths
--
Sqft
0.94
Acres
$3,000,000
4819 Tradewinds Dr, Sanibel, FL 33957
-- Beds
-- Baths
-- Sqft
0.94 Acres
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.
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Property Details
HOME DETAILS
0 Beds
0 Baths
0 Sqft
Built in 1958
0.94 Acres
1 Story
BEACH & VIEW
On Beachfront
FINANCIAL & COMMUNITY
$28,748 / yr property tax
Lee County
See More Details
Location
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Ad Statistics
Ad Number
7614595
Viewed
69 times
Listing Status
Active
Added
Apr 23, 2026
Last Refreshed
Jul 03, 2026 06:17:28 PM
Listing Information
Data Source
Florida Gulf Coast Multiple Listing Service, Inc.
Source Property ID
2026018790
Listing Agent: Dawn Marie Ramsey (License #: 280597316) 239-233-2976
Broker: Pfeifer Realty Group 239-472-0004 Listing Site
Copyright © 2026 Florida Gulf Coast Multiple Listing Service, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Broker: Pfeifer Realty Group 239-472-0004 Listing Site
Copyright © 2026 Florida Gulf Coast Multiple Listing Service, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
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