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.
Under contract
$3,995,000
87445 Old Hwy, Plantation Key, FL 33036
5beds
4,014sqft
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
- 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#: 620430
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
| Date | Event | Price |
|---|---|---|
| 8/4/2026 | Contingent | $3,995,000$995/sqft |
Source: | ||
| 6/27/2026 | Listed for sale | $3,995,000$995/sqft |
Source: | ||
| 6/27/2026 | Listing removed | $3,995,000$995/sqft |
Source: | ||
| 1/23/2026 | Listed for sale | $3,995,000-11.1%$995/sqft |
Source: | ||
| 12/5/2025 | Listing removed | $4,495,000$1,120/sqft |
Source: | ||
| 9/9/2025 | Listed for sale | $4,495,000-10%$1,120/sqft |
Source: | ||
| 6/17/2025 | Listing removed | $4,995,000$1,244/sqft |
Source: | ||
| 3/24/2025 | Price change | $4,995,000-9.1%$1,244/sqft |
Source: | ||
| 2/21/2025 | Price change | $5,495,000-8.3%$1,369/sqft |
Source: | ||
| 12/18/2024 | Price change | $5,995,000-4.8%$1,494/sqft |
Source: | ||
| 11/2/2024 | Listed for sale | $6,295,000+57.6%$1,568/sqft |
Source: | ||
| 11/18/2021 | Listing removed | -- |
Source: | ||
| 10/10/2021 | Price change | $3,995,000-4.9%$995/sqft |
Source: | ||
| 7/29/2021 | Price change | $4,199,000-5.6%$1,046/sqft |
Source: | ||
| 5/17/2021 | Listed for sale | $4,450,000+134.2%$1,109/sqft |
Source: | ||
| 4/4/2017 | Sold | $1,900,000-15.6%$473/sqft |
Source: | ||
| 1/20/2017 | Price change | $2,250,000-5.3%$561/sqft |
Source: Freewheeler Realty, Inc #571681 Report a problem | ||
| 8/15/2016 | Listed for sale | $2,375,000-8.6%$592/sqft |
Source: Freewheeler Realty, Inc #571681 Report a problem | ||
| 2/27/2016 | Listing removed | $2,599,000$647/sqft |
Source: Coldwell Banker Schmitt Real Estate Co. #569115 Report a problem | ||
| 6/2/2015 | Listed for sale | $2,599,000+36.8%$647/sqft |
Source: Coldwell Banker Schmitt Islamorada #567651 Report a problem | ||
| 6/11/2005 | Sold | $1,900,000$473/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax 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






