87445 Old Highway, Plantation Key, FL 33036
$3,995,000
Property Type:
Residential
Bedrooms:
5
Baths:
4
Square Footage:
4,014
Lot Size (sq. ft.):
79,399
Status:
Active
Current Price:
$3,995,000
List Date:
6/27/2026
Last Modified:
6/27/2026
Listing Details MLS# 620430
Location, Tax & Legal
- Street #
- 87445
- Street Name
- Old
- Street Suffix
- Highway
- Key/Island
- Plantation Key
- State/Province
- FL
- Zip Code
- 33036
- County
- Monroe
- Subdivision
- Plant Beach (87.5)
- Area
- 25 - Plantation Key
- City
- ISLAMORADA
- Mile Marker
- 87.5
- Marathon Neighborhood
- N/A
- Side
- Ocean
- Flood Zone
- AE,AE,AE,VE
- Alternate Key #
- 1511412
- Handicap Access
- No
- Parcel #
- 00415170000000
- Zoning
- RE - Residential Estate
- Deed Restrictions
- Unknown
- Legal
- Tr M Plantation Beach Pb2-76 Plantation Key Or559-723 Or781-687 Or1143-2292 Or1368-1602 Or1479-1205 Or1718-1824 Or2122-1
- Taxes
- 23895.75
- Tax Year
- 2025
- Pub Sewer HkUp
- Yes
Contract Information
- Listing Board
- Florida Keys
- As is Rght to Inspct
- Yes
- Species List
- Yes
General Property Description
- Realtor.COM Type
- Residential - Single Family
- Style
- Single Family
- Waterfront
- Yes
- Control Depth
- 3
- Pool
- Yes
- Year Built
- 1999
- Lot SqFt
- 79399
- Lot Sqft Source
- Property Data Card
- Acres
- 1.82
- Living Apx SqFt
- 4014
- SqFt Source
- Seller
- Total Bedrooms
- 5
- Full Baths
- 4
- Total Baths
- 4
- Rentals Allowed
- Yes
- Min Rental Days
- 7
- Total Units
- 0
Association Info
- Mandatory Home Owners Asc
- No
- 1st Right of Refusal
- No
- Association Fee $
- 0
Building Style
- Above Flood
- Unknown
- Stories
- 3 Stories
More Information
Pool Info
- Heated
- Yes
- In Ground
- Yes
- Salt Water
- Yes
Financial Status
- Standard Sale
- Yes
Remarks & Misc
- Remarks – Consumer
- 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.
- Directions
- Mile Marker 87 oceanside on Old Hwy
Fee Includes
- None
- Yes
Dockage
- Other Dockage
- Yes
Tax Exemptions
- None
- Yes
Appliances
- Dishwasher
- Yes
- Dryer
- Yes
- Microwave
- Yes
- More Appliances
- Yes
- Oven
- Yes
- Refrigerator
- Yes
- Stainless Steel Appliance(s)
- Yes
- Washer
- Yes
Pets
- Pets Allowed
- Yes
Cooling
- Ceiling Fans(s)
- Yes
- Central Air
- Yes
Heating
- Central
- Yes
- Electric
- Yes
Waterfront
- Oceanfront
- Yes
- Open Water
- Yes
Waterview
- Ocean View
- Yes
- Open Water View
- Yes
Floor
- Tile
- Yes
Interior Features
- Drapes/Blinds Incl
- Yes
- Entrance Foyer
- Yes
- Quartz Countertops
- Yes
- Split Bedroom
- Yes
- Window Treatments
- Yes
Windows/Doors
- Impact Rstnce Window
- Yes
- Sliding Glass Doors
- Yes
Vehicle Storage
- Carport
- Yes
- Covered Parking
- Yes
- Garage
- Yes
- Off Street Parking
- Yes
Security
- Electric Gate
- Yes
- Patrolled Area
- Yes
Construction
- CBS
- Yes
- Concrete
- Yes
Land Size
- 1 Less Than 2 Acres
- Yes
Furnished
- Negotiable
- Yes
Utilities
- FKAA
- Yes
- Municipal Sewer
- Yes
Porch/Balcony
- Open Porch/Balcony
- Yes
- Patio
- Yes
Title
- Title Ins - Buyer
- Yes
Exterior Features
- Privacy Wall/Fence
- Yes
Pre-Wired
- Cable
- Yes
Roof
- Metal Roof
- Yes
Shutters
- Accordion
- Yes
Property Features
Fee Includes:
None
Tax Exemptions:
None
Waterfront:
Oceanfront; Open Water
Waterview:
Ocean View; Open Water View
Dockage:
Other Dockage
Vehicle Storage:
Garage; Carport; Covered Parking; Off Street Parking
Furnished:
Negotiable
Cooling:
Ceiling Fans(s); Central Air
Heating:
Central
Utilities:
FKAA; Municipal Sewer
Interior Features:
Drapes/Blinds Incl; Entrance Foyer; Quartz Countertops; Split Bedroom; Window Treatments
Pre-Wired:
Cable
Appliances:
Dishwasher; Dryer; Microwave; More Appliances; Oven; Refrigerator; Stainless Steel Appliance(s); Washer
Exterior Features:
Privacy Wall/Fence
Pool Info:
In Ground; Salt Water
Construction:
CBS; Concrete
Shutters:
Accordion
Floor:
Tile
Roof:
Metal Roof
Pets:
Pets Allowed
Security:
Electric Gate; Patrolled Area
Land Size:
1 Less Than 2 Acres
Title:
Title Ins - Buyer
Listing Office:
Ocean Sotheby's International Realty
Last Updated: June - 27 - 2026
The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.