1009 Whitehead Street, Key West, FL

$2,800,000

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2

Beds

2

Baths

809

Square feet

1,307

Land Size

About 1009 Whitehead Street

High 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.

Features of 1009 Whitehead Street

MLS® # 620355
Price $2,800,000
Bedrooms 2
Bathrooms 2.00
Full Baths 2
Square Footage 809
Land Size 1,307
Year Built 1918
Type Residential
Sub-Type Single Family Residence
Style Conch
Status Active

Community Information

Address 1009 Whitehead Street
Area 01 - Key West
Subdivision Old Town - Unrecord (1.0)
City Key West
County Monroe
State FL
Zip Code 33040

Amenities

Utilities FKAA, Municipal Sewer
View No Waterview
Is Waterfront No
Waterfront None
Has Pool Yes
Pool In Ground, Salt Water, Decked

Interior

Interior Features Drapes/Blinds Incl, Cathedral Ceilings, Granite Counter Top, Dade County Pine
Appliances Washer, Dryer, Dishwasher, Refrigerator, Oven, Microwave
Cooling Central Air, Ceiling Fans(s)
Fireplace No
Stories 2 Stories
Has Basement No

Exterior

Lot Description Less Than 1/4 Acre
Windows Other Windows/Doors, Impact Rstnce Window, Impact Rstnce Doors
Roof Metal Roof
Construction Frame

Additional Information

Date Listed June 21st, 2026
Days on Market 18
Zoning HMDR - Historic Medium Density Residential
Short Sale No
RE / Bank Owned No

Listing Details

AgentBrenda J Donnelly
OfficeBrenda Donnelly Real Estate LLC

Listing Map

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