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$2,800,000
1009 Whitehead Street
Key West, FL 33040
MLS# 620355
2 beds  |  2 baths  |  809 sqft


Front View
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Front View Front View Front View Entry Kitchen Kitchen Kitchen Living Room Living Room Living Room Living Room Living Room Front Bedroom Front Bedroom Front Bedroom Front Bedroom Downstairs Bathroom Bonus Room Bonus Room Bonus Room Upstairs Loft Bedroom Upstairs Loft Bedroom Upstairs Loft Bedroom Upstairs Loft Bedroom Upstairs Loft Bedroom Upstairs Bathroom Pool Pool Pool Pool Pool Aerial View Aerial View Aerial View

Property Description
Income-Producing Transient Licensed Gem in the Heart of Old Town Key West! Rare opportunity to own a highly sought-after transient licensed vacation rental in one of Key West's most desirable Old Town locations. This charming 2-bedroom, 2-bath home also features a versatile bonus room, offering additional space for guests, a home office, or a creative retreat. Thoughtfully updated from top to bottom, the property boasts a new roof, A/C system, appliances, water heater, furniture, decking, pool and much more--providing a truly turnkey investment. A proven performer, this popular vacation rental enjoys strong occupancy, excellent reviews, and consistent income potential. ''Potter's Cottage'' a true Key West conch house, showcases artistic character and unique touches of the former owner who was a well known Key West potter, creating an authentic Key West experience that guests love. Outside, enjoy a beautifully refreshed salt water pool area, a covered lanai, an outdoor shower, new Trex decking, and inviting outdoor living spaces designed for relaxation and entertaining. The quaint front porch offers the perfect spot to unwind and soak in the vibrant neighborhood atmosphere. Ideally situated in the heart of Old Town, you're just steps from Duval Street, world-class dining, shopping, galleries, entertainment, and historic attractions. Leave the car behind--everything Key West has to offer is within easy walking or biking distance. Whether you're seeking a profitable investment, a personal island getaway, or the best of both worlds, this exceptional property delivers. A buyer can step into existing bookings and reputation on day one, proven 5.0 rating, 100 plus reviews and strong repeat bookings. Schedule your private showing today and discover this outstanding Key West opportunity.

Details
Maps
Contract Information
Listing Board: Key West Association
As is Rght to Inspct: Yes
Current Price: $2,800,000
Listing Date: 2026-06-21
List Price: $2,800,000
Location, Tax & Legal
KW Neighborhood: Old Town-S of Truman
City: KEY WEST
Off Shore Island: No
Mile Marker: 1
Marathon Neighborhood: N/A
Side: Median
Flood Zone: 0.2 PCT ANNUAL CHANC
Alternate Key #: 1028100
Parcel #: 00027330-000000
Zoning: HMDR - Historic Medium Density Residential
Deed Restrictions: Unknown
Legal: KW SUB 8 PT LOT 3 SQR 3 TR 11 ZZ-130 OR575-208/11 OR771-1386 OR822-1408/09 OR843-1957 OR892-2034 OR999-1824 OR1124-1871
Taxes: 8455.65
Tax Year: 2025
Pub Sewer HkUp: Yes
Street #: 1009
Street Name: Whitehead
Street Suffix: Street
Key/Island: Key West
State/Province: FL
Zip Code: 33040
County: Monroe
Subdivision: Old Town - Unrecord (1.0)
Area: 01 - Key West
General Property Description
Realtor.COM Type: Residential - Single Family
Waterfront: No
Control Depth: 0
Lot Size: X
Lot SqFt: 1442
Pool: Yes
Lot Sqft Source: Tax Records
Total Units: 0
Acres: 0.03
SqFt Source: Unknown/Condo
Rentals Allowed: Yes
Min Rental Days: 1
Style: Single Family
Year Built: 1918
Living Apx SqFt: 809
Total Bedrooms: 2
Full Baths: 2
Total Baths: 2
Remarks & Misc
Remarks – Consumer: Income-Producing Transient Licensed Gem in the Heart of Old Town Key West! Rare opportunity to own a highly sought-after transient licensed vacation rental in one of Key West's most desirable Old Town locations. This charming 2-bedroom, 2-bath home also features a versatile bonus room, offering additional space for guests, a home office, or a creative retreat. Thoughtfully updated from top to bottom, the property boasts a new roof, A/C system, appliances, water heater, furniture, decking, pool and much more--providing a truly turnkey investment. A proven performer, this popular vacation rental enjoys strong occupancy, excellent reviews, and consistent income potential. ''Potter's Cottage'' a true Key West conch house, showcases artistic character and unique touches of the former owner who was a well known Key West potter, creating an authentic Key West experience that guests love. Outside, enjoy a beautifully refreshed salt water pool area, a covered lanai, an outdoor shower, new Trex decking, and inviting outdoor living spaces designed for relaxation and entertaining. The quaint front porch offers the perfect spot to unwind and soak in the vibrant neighborhood atmosphere. Ideally situated in the heart of Old Town, you're just steps from Duval Street, world-class dining, shopping, galleries, entertainment, and historic attractions. Leave the car behind--everything Key West has to offer is within easy walking or biking distance. Whether you're seeking a profitable investment, a personal island getaway, or the best of both worlds, this exceptional property delivers. A buyer can step into existing bookings and reputation on day one, proven 5.0 rating, 100 plus reviews and strong repeat bookings. Schedule your private showing today and discover this outstanding Key West opportunity.
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0
License Info
# of City License: 1
Transient Rntl Licns: Yes
Fee Includes
None: 1
Dockage
None: 1
Tax Exemptions
None: 1
Appliances
Dishwasher: 1
Dryer: 1
Microwave: 1
Oven: 1
Refrigerator: 1
Washer: 1
Pets
Pets Allowed: 1
Cooling
Ceiling Fans(s): 1
Central Air: 1
Waterfront
None: 1
Waterview
No Waterview: 1
Floor
Tile: 1
Wood: 1
Interior Features
Cathedral Ceilings: 1
Dade County Pine: 1
Drapes/Blinds Incl: 1
Granite Counter Top: 1
Property Condition
Updated/Remodeled: 1
Building Style
Above Flood: Unknown
Conch: 1
Stories: 2 Stories
Windows/Doors
Impact Rstnce Doors: 1
Impact Rstnce Window: 1
Other Windows/Doors: 1
Construction
Frame: 1
Land Size
Less Than 1/4 Acre: 1
Furnished
Furnished: 1
Terms
Cash: 1
Conventional: 1
Utilities
FKAA: 1
Municipal Sewer: 1
Porch/Balcony
Deck: 1
Open Porch/Balcony: 1
Title
Negotiable: 1
Pool Info
In Ground: 1
Salt Water: 1
Decked: 1
Roof
Metal Roof: 1
Financial Status
Standard Sale: Yes
Status Change Info
Status: Active
Property Features
Fee Includes: None
Tax Exemptions: None
Waterfront: None
Waterview: No Waterview
Dockage: None
Property Condition: Updated/Remodeled
Building Style: Conch
Furnished: Furnished
Cooling: Ceiling Fans(s); Central Air
Utilities: FKAA; Municipal Sewer
Interior Features: Cathedral Ceilings; Dade County Pine; Drapes/Blinds Incl; Granite Counter Top
Appliances: Dishwasher; Dryer; Microwave; Oven; Refrigerator; Washer
Pool Info: In Ground; Salt Water; Decked
Construction: Frame
Floor: Tile; Wood
Roof: Metal Roof
Pets: Pets Allowed
Land Size: Less Than 1/4 Acre
Terms: Cash; Conventional
Title: Negotiable

Listing Office: Brenda Donnelly Real Estate LLC

Last Updated: June - 21 - 2026

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.