$3,995,000
 $21,446 est/mo Sourced by Back At You

87445 Old Highway,ISLAMORADA, FL 33036

ISLAMORADA, FL 33036

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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.

Details

MLS #620430
Listing TypeFor Sale
StyleHouse
Sub-TypeResale
StatusPending
Year1999
Days On Site58
Listing Provided ByOcean Sotheby's International Realty | Cheri Tindall

Features

Bed(s)5
Bath(s) 4 Total
SQ Feet4,014
PoolYes
ZoningRE - Residential Estate
Acreage1.82
Water FrontYes
Property ViewOpen Water View, Ocean

Taxes

Property23895

Area Information

StateFL
CountyMonroe
CityISLAMORADA
Zip Code33036
Area25 Plantation Key
Community NamePlant Beach (87.5)
Listing VS Median (in Plant Beach (87.5))
Price:
$3,995,000
low | high
Med:
$2,400,000
89.92491864831% of Average
sqft:
4,014
low | high
Med:
2,354
91.355256601893% of Average
$ / sqft:
$995
low | high
Med:
$994
50.135289829437% of Average
On site:
58
low | high
Med:
280
20.714285714286% of Average
Sourced by Back At You

Market Activity 33036

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Learn More About This Property

StateFL
CountyMonroe
CityISLAMORADA
Zip Code33036
Area25 Plantation Key
Community NamePlant Beach (87.5)
Listing VS Median (in Plant Beach (87.5))
Price:
$3,995,000
low | high
Med:
$2,400,000
89.92491864831% of Average
sqft:
4,014
low | high
Med:
2,354
91.355256601893% of Average
$ / sqft:
$995
low | high
Med:
$994
50.135289829437% of Average
On site:
58
low | high
Med:
280
20.714285714286% of Average
Sourced by Back At You
Nearby Listings (Within 1/4 mile)
Price: $2.996M - $4.993M
sqft: 3,000 - 5,000
Nearby Listings Property ImageNearby Listings Details
114 Royal Lane Property Photo 1
$25,000
114 Royal Lane
Plantation Key, FL 33036
Listing Updated: August 18, 2026 at 6:18:59 PM PDT
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