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1009 Whitehead Street, Key West, FL 33040

New Listing
$2,800,000
Property Type: Residential Bedrooms: 2 Baths: 2 Square Footage: 809 Lot Size (sq. ft.): 1,442 Status: Active
Current Price: $2,800,000 List Date: 6/21/2026 Last Modified: 6/22/2026

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.

More Information MLS# 620355

Contract Information

Current Price: $2,800,000 Listing Date: 2026-06-21 Listing Board: Key West Association List Price: $2,800,000 As is Rght to Inspct: Yes

Location Tax Legal

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 Style: Single Family Waterfront: No Pool: Yes Year Built: 1918 Lot Size: X Lot SqFt: 1442 Lot Sqft Source: Tax Records Acres: 0.03 Living Apx SqFt: 809 SqFt Source: Unknown/Condo Total Bedrooms: 2 Full Baths: 2 Total Baths: 2 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

# of City License: 1 Transient Rntl Licns: Yes

Building Style

Above Flood: Unknown Stories: 2 Stories

Financial Status

Standard Sale: Yes

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 - 22 - 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.

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