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1009 Whitehead Street, Key West, FL - photo 1

$2,800,000

1009 Whitehead Street

Key West, FL 33040

Estimated payment $14,733/month

HOA not listed, not included · estimated tax · estimated insurance · 20% down, 6.5%, 30 yr

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2Beds
2Baths
809Sq Ft
$3461Price/Sq Ft

Preferred partner

Kinsfolk Realty

Kinsfolk Signature Realty

Powered by Hometrino

(813) 602-0498

Highlights

Built in 1918
1,306 sqft Lot

About This Home

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.

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Facts & features

Bedrooms & bathrooms

  • •Bedrooms:2
  • •Bathrooms:2
  • •Full bathrooms:2
  • •Half bathrooms:0

Heating

  • •Has Heating:Yes

Interior area

  • •Total structure area:809 sqft
  • •Total interior livable area:809 sqft

Parking

  • •Parking features:N/A
  • •Garage spaces:0
  • •Has attached garage:No

Lot

  • •Size:1,306 sqft

Details

  • •Parcel number:N/A

Type & style

  • •Home type:Single Family Residence
  • •Property subtype:Residential

Materials

  • • N/A

Condition

  • •Year built:1918

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Price history

DateEventPrice
11/1/2026Listed for sale$2,800,000$3461/sqft

Listing Agent

Brenda J Donnelly

Brenda Donnelly Real Estate LLC

Brokerage Phone: 305-304-1116

Source: Florida Keys MLS · MLS #620355

Data Powered by Home Junction, Inc.

Nearby

Schools

KEY WEST MONTESSORI CHARTER SCHOOL, INC

Elementary · 0.7 mi

MAY SANDS MONTESSORI SCHOOL

Elementary · 0.9 mi

MONROE VIRTUAL INSTRUCTION PROGRAM

Elementary · 0.9 mi

Supermarkets

K

0.1 mi

Johnson's Grocery

0.2 mi

Island Grocery

0.4 mi

Dining

Grand Havana

0.1 mi

Italian Sea Food

0.1 mi

Origami Sushi Bar

0.1 mi

Parks

Nelson English City Park

0.2 mi

Key West Butterfly and Nature Consevatory

0.3 mi

Gato Village Pocket Park

0.3 mi

Beaches

South Beach

0.3 mi

Dog Beach

0.5 mi

Truman Beach

0.7 mi

Nearby amenity locations include data © OpenStreetMap contributors.