1011 Whitehead Street, Key West, FL 33040 (MLS# 621561)

1011 Whitehead Street, Key West, FL 33040

$3,795,000
Property Type: Residential Bedrooms: 3 Baths: 5 Square Footage: 2,024 Lot Size (sq. ft.): 1,125 Status: Active
Current Price: $3,795,000 List Date: 10/09/2026 Last Modified: 10/11/2026

Overview

Description

Rare Old Town mixed-use opportunity at 1011 Whitehead Street, just steps from Duval Street, the Key West Lighthouse and the Hemingway Home. This historic property features three beautifully updated, furnished one-bedroom residences, each with its own kitchen and transient rental license, allowing the units to be rented individually or together. Private patios and balconies add classic Key West charm, while a street-level commercial storefront provides an additional income-producing component. With three valuable transient licenses, flexible use and an iconic walkable location, this is a unique opportunity to own a distinctive piece of Key West.

Listing Details MLS# 621561

Location, Tax & Legal

Street #
1011
Street Name
Whitehead
Street Suffix
Street
Key/Island
Key West
State/Province
FL
Zip Code
33040
County
Monroe
Subdivision
Old Town - Unlisted (1.0)
Area
02 - Key West

Contract Information

Listing Board
Key West Association
As is Rght to Inspct
Yes

General Property Description

Realtor.COM Type
Multi-family
Style
Multi-Units
Waterfront
No
Pool
No
Year Built
1918
Total Units
4
Lot SqFt
1125
Lot Sqft Source
Tax Records
Acres
0.03
Living Apx SqFt
2024
SqFt Source
Tax Records
Total Bedrooms
3
Full Baths
3
Half Baths
2
Total Baths
5
Rentals Allowed
Yes
Min Rental Days
Yes

Association Info

Mandatory Home Owners Asc
No
1st Right of Refusal
No

License Info

Transient Rntl Licns
Yes

More Information

Building Style

Above Flood
Unknown
# Stories
3 Stories

Property Features

Fee Includes: None Tax Exemptions: None Waterfront: None Waterview: No Waterview Dockage: None Furnished: Furnished Cooling: Ductless Utilities: Elect Separate Meter; FKAA; Municipal Sewer Interior Features: Built-in Cabinets; Drapes/Blinds Incl; Granite Counter Top; Storage; Window Treatments Appliances: Dishwasher; Microwave; Oven; Range; Refrigerator Construction: Frame Pets: Pets Allowed Land Size: Less Than 1/4 Acre
Listing Office: Realty ONE Group Destination
Last Updated: October - 11 - 2026
Broker Attribution: rogdestination@gmail.com
The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.
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