87445 Old Highway, Plantation Key, FL

$3,995,000

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5

Beds

4

Baths

4,014

Square feet

1.82

Acres

About 87445 Old Highway

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.

Features of 87445 Old Highway

MLS® # 620430
Price $3,995,000
Bedrooms 5
Bathrooms 4.00
Full Baths 4
Square Footage 4,014
Acres 1.82
Year Built 1999
Type Residential
Sub-Type Single Family Residence
Status Active

Community Information

Address 87445 Old Highway
Area 25 - Plantation Key
Subdivision Plant Beach (87.5)
City Plantation Key
County Monroe
State FL
Zip Code 33036

Amenities

Utilities FKAA, Municipal Sewer
Parking Garage, Carport, Off Street Parking, Covered Parking
View Ocean View, Open Water View
Is Waterfront Yes
Waterfront Oceanfront, Open Water
Has Pool Yes
Pool In Ground, Salt Water

Interior

Interior Features Drapes/Blinds Incl, Split Bedroom, Entrance Foyer, Window Treatments, Quartz Countertops
Appliances More Appliances, Washer, Dryer, Dishwasher, Refrigerator, Oven, Microwave, Stainless Steel Appliance(s)
Heating Central, Electric
Cooling Central Air, Ceiling Fans(s)
Fireplace No
Stories 3 Stories
Has Basement No

Exterior

Exterior Features Privacy Wall/Fence
Lot Description 1 Less Than 2 Acres
Windows Sliding Glass Doors, Impact Rstnce Window
Roof Metal Roof
Construction CBS, Concrete

Additional Information

Date Listed June 26th, 2026
Days on Market 1
Zoning RE - Residential Estate
Short Sale No
RE / Bank Owned No

Listing Details

AgentCheri Tindall
OfficeOcean Sotheby's International Realty

Listing Map

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