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Property Description
Opportunities like this don't come along often. Own a prime piece of Sanibel Island-or three. Now cleared and ready for reconstruction, the Tropical Winds portfolio presents a rare opportunity to reimagine multiple income-producing parcels in one of the island's most exclusive and tightly regulated sectors-nightly rentals. In a market where most properties are limited to 30-day minimums, this offering stands apart with zoning that allows for 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. This rare combination positions the offering well above typical investment opportunities on the island. The properties were impacted by Hurricane Ian and have been cleared, offering a blank canvas for new, elevated construction. Sanibel's post-Ian Build-Back provisions allow for 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 advantage on the coast. This is a unique chance to develop higher-end accommodations while retaining the valuable nightly rental zoning that makes this portfolio truly exceptional. Additional properties included in this package: 1344 Jamaica Drive - Lot zoned for duplex construction 1350 Jamaica Drive - Lot zoned for duplex construction
Full Property Details
Full Property Details for 4819 Tradewinds Dr
General
- Price: $3,000,000
- Taxes: $28,748 (2024)
- Status: Active
- Type: Business
- Source: Bonita_Springs
- MLS ID: 2026018790
- Updated: 4/23/2026
- Added to Site: 1 day(s) ago
Business
- Business Type: Business w/Property
Location
- Area: SI01 - Sanibel Island
- County: Lee
- Driving Directions: USE GPS
Structural Information
- Description/Design: Lodging and Hospitality: Economy/Limited Service
- Stories/Levels: 1
- Stories in Building: 1
- Current Bldg. Use: Business
- Year Built: 1958
Lot Features
- Lot Size (Acres): 0.941
- Lot Size (Sq. Ft.): 40,989
- Lot Size Source: Property Appraiser Office
- Frontage Feet: 100
Water Features
- Water Front: Yes
- Water Front Desc.: Gulf Frontage
- Canal Width: None
Financial Considerations
- Price Per Acre: $1,062
- Assoc Fee Freq.: Annually
- Tax Amount: $28,748
- Tax Year: 2024
Disclosures and Reports
- Legal Description: TRADEWINDS PB 11 PG 13 LOT 28
- Inclusions: Building And Land, Business, Trade Name
- Property ID: 19-46-22-T2-00400.0280
Listed by Pfeifer Realty Group LLC
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Schools
Schools serving 4819 Tradewinds Dr
School District:Lee County School District, Fort Myers, FL
| Name | Grades | Distance |
|---|---|---|
The Sanibel School 3840 Sanibel Captiva Road, Sanibel, FL 33957 | 6-8 | 1.6 mi |
Cypress Lake High School 6750 Panther Lane, Fort Myers, FL 33919 | 9-12 | 16.1 mi |
South Fort Myers High School 14020 Plantation Road, Fort Myers, FL 33912 | 9-12 | 19.2 mi |
Fort Myers High School 2635 Cortez Boulevard, Fort Myers, FL 33901 | 9-12 | 20.4 mi |
Estero High School 21900 River Ranch Road, Estero, FL 33928 | 9-12 | 21.5 mi |
Dunbar High School 3800 Edison Avenue, Fort Myers, FL 33916 | 9-12 | 22.7 mi |
Bonita Springs High School 25592 Imperial Parkway, Bonita Springs, FL 34135 | 9-12 | 23.8 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 4819 Tradewinds Dr
Date
Details
Price
Change
Source
4/23/2026
Listed
$3,000,000
252.94%
MLS
12/20/2000
Sold
$850,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 4819 Tradewinds Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$28,865
-4%
$1,815,047
—
2024
$29,946
-1%
$1,815,047
—
2023
$30,337
13%
$1,815,047
15%
2021
$26,750
-11%
$1,582,340
-26%
2022
$30,199
13%
$2,136,181
35%
2021
$26,750
9%
$1,581,544
15%
2018
$24,599
-9%
$1,371,732
-8%
2017
$26,935
3%
$1,495,290
—
2016
$26,189
10%
$1,495,347
21%
2015
$23,786
3%
$1,234,091
4%
2014
$23,153
-6%
$1,186,889
-15%
2019
$24,574
9%
$1,399,439
19%
2013
$22,566
—
$1,172,663
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 4819 Tradewinds Dr
4819 Tradewinds Dr, Sanibel, FL 33957 (MLS# 2026018790) is a Business property. 4819 Tradewinds Dr is currently listed for $3,000,000 and was received on April 23, 2026. Want to learn more about 4819 Tradewinds Dr? Do you have questions about finding other Business real estate for sale in Sanibel? You can browse all Sanibel real estate or contact a Coldwell Banker agent to request more information.

