1011 Whitehead Street, Key West, FL 33040
New Listing
$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
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.
More Information MLS# 621561
Contract Information
Current Price: $3,795,000
Listing Date: 2026-10-09
Listing Board: Key West Association
List Price: $3,795,000
As is Rght to Inspct: Yes
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
General Property Description
Realtor.COM Type: Multi-family
Style: Multi-Units
Waterfront: No
Pool: No
Year Built: 1918
Total Units: 4
Lot Size: X
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: 1
Status Change Info
Status: Active
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
License Info
Transient Rntl Licns: Yes
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.