87445 Old Highway

Property Description

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.

Overview

Property Status

Sold

Date Sold

October 1, 2026

Lot Size

1.82 Acres

MLS ID

620430

Property Type

Residential

Year Built

1999

Are you interested?

Schedule a Tour

Caroline Hendrix

(786) 847-3705 [email protected]

Features & Amenities

Total Area

4,014 Sq.Ft.

Neighborhood

Plantation Key

Architecture Styles

Above Flood

View Description

Open Water View, Ocean

Pool

Heated, Salt Water, In Ground

Roof

Metal

Parking

Off Street, Covered, Carport

Heat Type

Central, Electric

Air Conditioning

Central Air, Ceiling Fans(s)

Appliances

Stainless Steel Appliance(s), Dishwasher, Dryer, Microwave, More Appliances, Oven, Refrigerator, Washer

Other Interior Features

Entrance Foyer, Drapes/Blinds Incl, Quartz Countertops, Split Bedroom, Window Treatments

Security Features

Electric Gate, Patrolled Area

Other Exterior Features

Privacy Wall/Fence

Sales Price

$3,700,000

Real Estate Tax

$23,896/yr

Zoning

RE - Residential Estate

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I would love to help you see this beautiful home! As a full-service real estate agent, I can help you tour. Please submit an offer, and answer questions about the buying process.

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