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Sold for $3,700,000
  • $3,700,000

    87445 Old Hwy, Plantation Key, FL 33036

    5beds
    4,014sqft
    Single Family Residence
    Built in 1999
    1.82 Acres Lot
    $3,701,700 Zestimate®
    $922/sqft
    $-- Estimated rent

    Home value

    $3,701,700

    $3.33M - $4.11M

    Not available

    Zestimate® history
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    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.

    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

    Bought with:

    Caroline Hendrix, 3544880

    Coldwell Banker Schmitt Islamorada

    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

    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: $922/sqft
    • Tax assessed value: $2,832,663
    • Annual tax amount: $23,895
    • Date on market: 6/27/2026

    Price history

    DateEventPrice
    10/1/2026Sold$3,700,000-7.4%$922/sqft
    Source: FLKMLS #620430 Report a problem
    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

    Neighborhood: 33036

    Nearby schools

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    Estimated market value
    $3,701,700
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    Estimated market value
    $3,701,700