
Land with Home for Sale in Plantation Key, Florida
87445 Old Hwy, Plantation Key, FL 33036
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.
Location
- Street address
- 87445 Old Hwy
- County
- Monroe County
- Zip code
- 33036
- Community
- Plant Beach (87.5)
- Elevation
- 2 feet
Directions
Mile Marker 87 oceanside on Old Hwy
Property details
- Acreage
- 1.82 acres79,279 sq ft
- Zoning
- RE - Residential Estate
- MLS #
- FLKEYSMLS 620430
- Posted
Property taxes
- 2025
- $23,896
Parcels
- 00415170000000
Legal description
Tr M Plantation Beach Pb2-76 Plantation Key Or559-723 Or781-687 Or1143-2292 Or1368-1602 Or1479-1205 Or1718-1824 Or2122-1
Details and features
Listing
- Type
- Residential
- Subtype
- Single Family Residence
Lot
- View
- Ocean, Water
- Waterfront
- Ocean Front
Exterior
- Fencing
- Privacy
- Pool
- Patio, Porch
- Features
- Privacy Wall/Fence
Structure
- Heating
- Central, Electric
- Cooling
- Central Air
- Materials
- CBS, Concrete
- Roof
- Metal
Interior
- Rooms
- Bathroom x 4, Bedroom x 5
- Flooring
- Tile
- Appliances
- Dishwasher, Dryer, Microwave, More Appliances, Oven, Refrigerator, Stainless Steel Appliance(s), Washer
- Features
- Quartz Countertops
Listing history
| Date | Event | Price | Change | Source |
|---|---|---|---|---|
| Jan 23, 2026 | New listing | $3,995,000 | — | FLKEYSMLS |
| Dec 6, 2025 | Listing removed | $4,495,000 | — | Listing agent |
| Sept 10, 2025 | New listing | $4,495,000 | — | FLKEYSMLS |
































