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.
For sale
$2,800,000
1009 Whitehead St, Key West, FL 33040
2beds
809sqft
Single Family Residence
Built in 1918
1,306 Square Feet Lot
$2,586,900 Zestimate®
$3,461/sqft
$-- HOA
What's special
Covered lanaiNew roofVersatile bonus roomQuaint front porchOutdoor shower
- 12 days |
- 873 |
- 25 |
Zillow last checked:
Listing updated:
Listed by:
Brenda J Donnelly 305-304-1116,
Brenda Donnelly Real Estate LLC
Source: FLKMLS,MLS#: 620355
Originating MLS: Key West Association
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 2
- Full bathrooms: 2
Cooling
- Central Air, Ceiling Fans(s)
Appliances
- Included: Washer, Microwave, Oven, Refrigerator, Dishwasher, Dryer
Features
- Dade County Pine, Granite Counters, Cathedral Ceiling(s)
- Flooring: Tile, Wood
- Doors: Impact Rstnce Doors
- Windows: Drapes/Blinds Incl, Other Windows/Doors, Impact Rstnce Window
- Furnished: Yes
Interior area
- Total interior livable area: 809 sqft
Property
Features
- Levels: Two
- Stories: 2
- Patio & porch: Open Porch/Balcony, Deck
- Has private pool: Yes
- Pool features: In Ground, Decked, Salt Water
- Water view: None
- Waterfront features: None, Dockage: None
Lot
- Size: 1,306 Square Feet
- Features: Less Than 1/4 Acre
Details
- Parcel number: 00027330000000
- Zoning: HMDR
- Zoning description: Historic Medium Density Residential
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Conch
- Property subtype: Single Family Residence
Materials
- Frame
- Roof: Metal
Condition
- Updated/Remodeled
- New construction: No
- Year built: 1918
Utilities & green energy
- Sewer: Municipal Sewer, Public Sewer
- Utilities for property: FKAA
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
Estimated market value
$2,586,900
$2.46M - $2.72M
$4,787/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/21/2026 | Listed for sale | $2,800,000+211.5%$3,461/sqft |
Source: | ||
| 8/1/2014 | Sold | $899,000+97.1%$1,111/sqft |
Source: | ||
| 1/24/2011 | Sold | $456,000+30.3%$564/sqft |
Source: | ||
| 6/8/2000 | Sold | $350,000$433/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax 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 | $456,899 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: Upper Duvall
Nearby schools
GreatSchools rating
- 3/10Horace O'bryant SchoolGrades: PK-8Distance: 1 mi
- 4/10Key West High SchoolGrades: 9-12Distance: 1.5 mi
A local agent can set up tours, give advice and negotiate with sellers.
- Florida
- Monroe County
- Key West
- 33040
- Upper Duvall
- 1009 Whitehead St




