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$3,795,000 Just Listed

  • For Sale
  • Active
  • Multi-Family
  • 4 Units
  • 0.03 Acres
  • Updated 1 day ago
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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.

Full Property Details for 1011 Whitehead St

General

  • Price: $3,795,000
  • Taxes: $8,504 (2025)
  • Status: Active
  • Type: Multi-Family
  • Source: 927
  • MLS ID: 621561
  • Updated: 10/9/2026
  • Added to Site: 3 day(s) ago

Interior

  • Interior Features: Built-in Cabinets, Drapes/Blinds Incl, Granite Counter Top, Storage, Window Treatments
  • Appliances: Dishwasher, Microwave, Oven, Range, Refrigerator

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 3
  • Half Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3

Exterior

  • Deck/Patio: Open Porch/Balcony, Deck
  • Porch/Patio/Deck: Open Porch/Balcony, Deck

Location

  • Area: 02 - Key West
  • County: Monroe
  • Subdivision: Old Town - Unlisted (1.0)

Community

  • Assoc. Fees Include: None
  • Pets Allowed: Yes

Heating & Cooling

  • Air Conditioning: Yes
  • Cooling Type: Ductless

Structural Information

  • Architectural Style: Above Flood
  • Construction: Frame
  • Square Feet: 2,024
  • Sq. Ft. Source: Tax Records
  • Year Built: 1918

Unit Information

  • Units in Building: 4

Lot Features

  • Property View: No Waterview
  • Lot Size (Acres): 0.03
  • Lot Size (Sq. Ft.): 1,125
  • Lot Size Source: Tax Records
  • Lot Dimensions: x
  • Zoning: HMDR - Historic Medium Density Residential

Water Features

  • Water View: Yes

Financial Considerations

  • Tax Amount: $8,504.34
  • Tax Year: 2025

Disclosures and Reports

  • Legal Description: 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
  • Flood Zone: 0.2 PCT ANNUAL CHANC
  • APN: 00027330-000200

Listed by Realty ONE Group Destination, Stacy Stahl (305) 731-9510

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Listing agent

— 1011 Whitehead St —

  • Stacy Stahl

    Realty ONE Group Destination

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 1011 Whitehead St

School District:Monroe County School District, Middle Torch Key, FL
NameGradesDistance
Horace O'bryant School
1105 Leon Street, Key West, FL 33040
6-81 mi
Key West High School
2100 Flagler Avenue, Key West, FL 33040
9-121.5 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 1011 Whitehead St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/09/2026
Listed
$3,795,000
660.52%
MLS
2/18/2014
Sold
$499,000
—
Public Record
Get Price Alerts and Save Property
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 for 1011 Whitehead St

Year
Property Taxes
Change
Tax Assessment
Change
2024
$7,545
—
$849,831
15%
2024
$7,545
4%
$741,798
6%
2023
$7,264
14%
$701,694
20%
2021
$6,380
-7%
$586,223
-18%
2022
$6,827
7%
$713,798
30%
2021
$6,380
13%
$547,297
14%
2019
$5,659
16%
$478,902
10%
2018
$4,870
21%
$435,367
10%
2017
$4,041
-5%
$395,788
—
2016
$4,251
-3%
$395,583
—
2015
$4,364
-3%
$395,465
1%
2014
$4,505
7%
$393,169
9%
2013
$4,219
—
$361,222
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Realty ONE Group Destination, Stacy Stahl (305) 731-9510

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1011 Whitehead Street, Key West, FL 33040 (MLS# 621561) is a Multi-Family property with 4 units containing 3 bedrooms, 3 full bathrooms and 2 partial bathrooms. 1011 Whitehead Street is currently listed for $3,795,000 and was received on October 09, 2026. Want to learn more about 1011 Whitehead Street? Do you have questions about finding other Multi-Family real estate for sale in Key West? You can browse all Key West real estate or contact a Coldwell Banker agent to request more information.

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