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For sale
$2,800,000
2beds
809sqft

1009 Whitehead St, Key West, FL 33040

2beds
809sqft
Single family residence
Built in 1918
1,306 sqft
No data
$3,461 price/sqft

What's special

Covered lanaiNew roofVersatile bonus roomNew trex deckingQuaint front porchWater heaterOutdoor shower

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.

104 days
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792
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37
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Source: FLKMLS,MLS#: 620355MLS Logo
Travel times

Living Room

Kitchen

Bedroom

Zillow last checked:

Listing updated:

Listed by:

Brenda J Donnelly 305-304-1116,

Brenda Donnelly Real Estate LLC

Source: FLKMLS,MLS#: 620355MLS Logo

Facts & features

Interior

Bedrooms & bathrooms
  • Bedrooms: 2
  • Bathrooms: 2
  • Full bathrooms: 2
Cooling
  • Central Air, Ceiling Fans(s)
Appliances
  • Included: Washer, Dryer, Dishwasher, Refrigerator, Oven, Microwave
Features
  • Granite Counters, Dade County Pine
  • Flooring: Tile, Wood
  • Furnished: Yes
Interior area
  • Total structure area: 809
  • Total interior livable area: 809 sqft
Video & virtual tour

Property

Features
  • Patio & porch: Open Porch/Balcony, Deck
  • Has private pool: Yes
  • Pool features: In Ground, Salt Water, Decked
Lot
  • Size: 1,306 Square Feet
Details
  • Parcel number: 00027330000000
  • Zoning: HMDR - Historic Medium Density Residential

Construction

Type & style
  • Home type: SingleFamily
  • Architectural style: Conch
  • Property subtype: Single Family Residence
Materials
  • Frame
Condition
  • Updated/Remodeled
  • New construction: No
  • Year built: 1918

Community & HOA

Community
  • Subdivision: Old Town - Unrecord (1.0)
HOA
  • Has HOA: No
  • Services included: None
Location
  • Region: Key West

Financial & listing details

  • Price per square foot: $3,461/sqft
  • Tax assessed value: $1,027,931
  • Annual tax amount: $8,455
  • Date on market: 6/21/2026
  • Listing terms: Cash,Conventional

Price history

DateEventPrice
6/21/2026Listed for sale$2,800,000+211.5%$3,461/sqft
Source: Key West AOR #620355
8/1/2014Sold$899,000+97.1%$1,111/sqft
Source: FLKMLS #120181
1/24/2011Sold$456,000+30.3%$564/sqft
Source: FLKMLS #113990
6/8/2000Sold$350,000$433/sqft
Source: Public Record

Public tax history

YearProperty taxesTax assessment
2025$8,456 +7.2%$921,171 +10%
2024$7,885 +8.8%$837,428 +10%
2023$7,247 +12.6%$761,298 +10%
2022$6,434 +8.4%$692,089 +10%
2021$5,937 +0.4%$629,172 +0.2%
2020$5,916 $628,081 -3%
2019$5,916 +3.7%$647,376 +4.8%
2018$5,707 +5.3%$617,946 +31%
2017$5,419 +14.4%$471,887 -1.8%
2016$4,739 -6.7%$480,577 +5.2%
2015$5,077 $456,899

Find assessor info on the county website

Monthly payment

Est. payment
$17,396/mo
Principal & interest
$15483
Property taxes
$1913
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Estimated market value

Not available

Estimated sales range

Not available

Not available

Climate risks

Explore flood, wildfire, and other predictive climate risk information for this property on First Street®️.

Neighborhood: Upper Duvall

Nearby schools

Horace O'bryant School
Grades PK-8 • 1 miles
3/10
GreatSchools® Rating
Test Score Rating
3/10
Student Progress Rating
3/10
Key West High School
Grades 9-12 • 1.5 miles
4/10
GreatSchools® Rating
Test Score Rating
4/10
College Readiness Rating
5/10
Student Progress Rating
2/10