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: 10/09/2026

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
KW Neighborhood: Old Town-S of Truman
City: KEY WEST
Mile Marker: 0.5
Marathon Neighborhood: N/A
Side: Median
Flood Zone: 0.2 PCT ANNUAL CHANC
Alternate Key #: 8682425
Parcel #: 00027330-000200
Zoning: HMDR - Historic Medium Density Residential
Deed Restrictions: Unknown
Legal: KW PT SUB 8 PT LOT 3 SQR 3 TR 11 OR950-337 OR1012-1916R/S OR1094-2147 OR1460-262/63R/S OR1637-811/12 OR2089-1776AFF OR21
Taxes: 8504.34
Tax Year: 2025
Pub Sewer HkUp: Yes

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
Control Depth: 0

Association Info

Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0

License Info

Transient Rntl Licns: Yes

More Information

Building Style

Above Flood: Unknown
Stories: 3 Stories

Remarks & Misc

Remarks – Consumer: 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.

Fee Includes

None: Yes

Dockage

None: Yes

Tax Exemptions

None: Yes

Appliances

Dishwasher: Yes
Microwave: Yes
Oven: Yes
Range: Yes
Refrigerator: Yes

Pets

Pets Allowed: Yes

Cooling

Ductless: Yes

Waterfront

None: Yes

Waterview

No Waterview: Yes

Interior Features

Built-in Cabinets: Yes
Drapes/Blinds Incl: Yes
Granite Counter Top: Yes
Storage: Yes
Window Treatments: Yes

Construction

Frame: Yes

Land Size

Less Than 1/4 Acre: Yes

Furnished

Furnished: Yes

Utilities

Elect Separate Meter: Yes
FKAA: Yes
Municipal Sewer: Yes

Porch/Balcony

Deck: Yes
Open Porch/Balcony: Yes

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 - 09 - 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.

Search powered by FBS Products