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For sale
  • $2,800,000

    1009 Whitehead St, Key West, FL 33040

    2beds
    809sqft
    : 
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    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
    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.
    12 days
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    873
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    25
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    Zillow last checked:

    Listing updated:

    Listed by:

    Brenda J Donnelly 305-304-1116,

    Brenda Donnelly Real Estate LLC

    Source: FLKMLS,MLS#: 620355MLS LogoOriginating 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

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

        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

        Payment breakdown

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        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

        Getting around

        95 / 100
        Walker's Paradise
        28 / 100
        Some Transit
        82 / 100
        Very Bikeable

        Nearby schools

        GreatSchools rating

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