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Under contract
  • $3,995,000

    87445 Old Hwy, Plantation Key, FL 33036

    5beds
    4,014sqft
    : 
    $24,733/mo
    Get pre-qualified
    Single Family Residence
    Built in 1999
    1.82 Acres Lot
    $-- Zestimate®
    $995/sqft
    $-- HOA

    What's special

    Oceanfront estateGated entranceExceptional craftsmanship throughoutFive spacious bedroomsQuartz countertopsElegant wrought-iron staircaseBreathtaking ocean views throughout
    Discover a rare opportunity to own an exceptional oceanfront estate in the heart of Islamorada that seamlessly combines luxury living with an established, successful vacation rental history. Situated on 1.82 private acres with approximately 225 feet of ocean frontage, this Residential Estate-zoned property is currently licensed for legal 7-day vacation rentals, making it one of the limited number of properties within the Village of Islamorada offering this highly sought-after privilege. With a documented history as a successful income-producing vacation rental, this property offers the opportunity to enjoy an extraordinary Florida Keys lifestyle while rental income may help offset the costs of ownership. A gated entrance welcomes you through a majestic Royal Palm-lined circular driveway to an impressive, covered portico. Inside, a dramatic foyer and elegant wrought-iron staircase set the tone for a home featuring five spacious bedrooms, four beautifully appointed bathrooms, and breathtaking ocean views throughout. Enjoy spectacular sunrises from the observation pier or relax year-round in the heated and chilled saltwater pool. The home is beautifully appointed with quartz countertops, premium appliances, impact-resistant windows, and exceptional craftsmanship throughout. Whether you're seeking a luxurious private residence or a proven income-producing property to help offset costs, this ideal combination of both is a remarkable Islamorada estate that offers an exceptional blend of privacy, oceanfront beauty, and one of the most desirable licensed weekly vacation rental opportunities in the Florida Keys.
    63 days
    424
    14

    Zillow last checked:

    Listing updated:

    Listed by:

    Cheri Tindall 305-664-7661,

    Ocean Sotheby's International Realty,

    Leslie Leopold 305-942-0215,

    Ocean Sotheby's International Realty

    Source: FLKMLS,MLS#: 620430MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 4
      • Full bathrooms: 4
      Heating
      • Has Heating (Unspecified Type)
      Cooling
      • Central Air, Ceiling Fans(s)
      Appliances
      • Included: More Appliances, Washer, Dryer, Dishwasher, Refrigerator, Oven, Microwave, Stainless Steel Appliance(s)
      Features
      • Quartz Countertops
      • Flooring: Tile
      Interior area
      • Total structure area: 4,014
      • Total interior livable area: 4,014 sqft
      Video & virtual tour

      Property

      Parking
      • Parking features: Garage
      • Has garage: Yes
      Features
      • Patio & porch: Open Porch/Balcony, Patio
      • Has private pool: Yes
      • Pool features: In Ground, Salt Water
      • Fencing: Privacy
      • On waterfront: Yes
      Lot
      • Size: 1.82 Acres
      Details
      • Parcel number: 00415170000000
      • Zoning: RE - Residential Estate

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • CBS, Concrete
      Condition
      • Year built: 1999

      Community & HOA

      Community
      • Security: Security Gate, Security Guard
      • Subdivision: Plant Beach (87.5)
      HOA
      • Has HOA: No
      • Services included: None
      Location
      • Region: Plantation Key

      Financial & listing details

      • Price per square foot: $995/sqft
      • Tax assessed value: $2,832,663
      • Annual tax amount: $23,895
      • Date on market: 6/27/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        8/4/2026Contingent$3,995,000$995/sqft
        Source: Key West AOR #620430 Report a problem
        6/27/2026Listed for sale$3,995,000$995/sqft
        Source: Key West AOR #620430 Report a problem
        6/27/2026Listing removed$3,995,000$995/sqft
        Source: FLKMLS #616426 Report a problem
        1/23/2026Listed for sale$3,995,000-11.1%$995/sqft
        Source: Key West AOR #616426 Report a problem
        12/5/2025Listing removed$4,495,000$1,120/sqft
        Source: Key West AOR #616426 Report a problem
        9/9/2025Listed for sale$4,495,000-10%$1,120/sqft
        Source: Key West AOR #616426 Report a problem
        6/17/2025Listing removed$4,995,000$1,244/sqft
        Source: FLKMLS #612079 Report a problem
        3/24/2025Price change$4,995,000-9.1%$1,244/sqft
        Source: FLKMLS #612079 Report a problem
        2/21/2025Price change$5,495,000-8.3%$1,369/sqft
        Source: FLKMLS #612079 Report a problem
        12/18/2024Price change$5,995,000-4.8%$1,494/sqft
        Source: FLKMLS #612079 Report a problem
        11/2/2024Listed for sale$6,295,000+57.6%$1,568/sqft
        Source: FLKMLS #612079 Report a problem
        11/18/2021Listing removed--
        Source: FLKMLS #596107 Report a problem
        10/10/2021Price change$3,995,000-4.9%$995/sqft
        Source: Key West AOR #596107 Report a problem
        7/29/2021Price change$4,199,000-5.6%$1,046/sqft
        Source: FLKMLS #596107 Report a problem
        5/17/2021Listed for sale$4,450,000+134.2%$1,109/sqft
        Source: FLKMLS #596107 Report a problem
        4/4/2017Sold$1,900,000-15.6%$473/sqft
        Source: FLKMLS #571681 Report a problem
        1/20/2017Price change$2,250,000-5.3%$561/sqft
        Source: Freewheeler Realty, Inc #571681 Report a problem
        8/15/2016Listed for sale$2,375,000-8.6%$592/sqft
        Source: Freewheeler Realty, Inc #571681 Report a problem
        2/27/2016Listing removed$2,599,000$647/sqft
        Source: Coldwell Banker Schmitt Real Estate Co. #569115 Report a problem
        6/2/2015Listed for sale$2,599,000+36.8%$647/sqft
        Source: Coldwell Banker Schmitt Islamorada #567651 Report a problem
        6/11/2005Sold$1,900,000$473/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$23,896 +8.2%$2,426,610 +10%
        2024$22,085 +4.3%$2,206,009 +10%
        2023$21,165 +12.3%$2,005,463 +10%
        2022$18,848 +11.2%$1,823,148 +10%
        2021$16,945 -1.1%$1,657,407 -0.7%
        2020$17,131 $1,669,333 +6.4%
        2019$17,131 -2%$1,568,872 -8.8%
        2018$17,487 -7.4%$1,720,080 -23.3%
        2017$18,890 -19.8%$2,243,679 +1.5%
        2016$23,567 -0.4%$2,210,509 -1.5%
        2015$23,661 $2,243,553
        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.
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        Climate risks

        Neighborhood: 33036

        Getting around

        19 / 100
        Car-Dependent
        53 / 100
        Bikeable

        Nearby schools

        GreatSchools rating

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