87445 Old Hwy
Contingent

87445 Old Highway HIGHWAY

Islamorada, FL 33036
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$3,995,000 $16,843/Mo
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Bed 5

Bed

Bath 4

Bath

SqFt4,014

Sqft

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 a n 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.

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Detail Ic Property Details

Property Type : Residential - Single Family

Price : $3,995,000

AD Id : 86614444

MLS Id : 620430

Beds : 5

Living Area Size : 4,014

Year Built : 1999

County : Monroe

Subdivision: Oasis

  • Map Map

Map

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Feature Features

  • Bedroom Information

    Total Bedrooms: 5

    Bathroom Information

    Total Baths: 4 Full Baths: 4

  • Interior Features

    Drapes/Blinds Incl,Quartz Countertops,Window Treatments,Entrance Foyer,Split Bedroom Appliances: More Appliances,Stainless Steel Appliance(s),Microwave,Oven,Refrigerator,Dishwasher,Dryer,Washer

  • Roofing Information

    Metal Roof

    Flooring Information

    Tile

    Heating & Cooling

    Cooling: Central Air,Ceiling Fans(s) Heating: Central,Electric Water Front: Yes Oceanfront,Open Water Ocean View,Open Water View

    Window Information

    Window Treatments: Sliding Glass Doors,Impact Rstnce Window

  • Building Information

    Year Built: 1999 Total Units: 0.00 Floor Location: 79399 Construction: CBS,Concrete Security System: Electric Gate,Patrolled Area Roof: Metal Roof

  • Exterior Features

    Privacy Wall/Fence

    Pool Information

    In Ground,Salt Water Heated: Yes

  • Lot Information

    Lot SqFt: 79,399 Lot SqFt Source: Property Data Card Tr M Plantation Beach Pb2-76 Plantation Key Or559-723 Or781-687 Or1143-2292 Or1368-1602 Or1479-1205 Or1718-1824 Or2122-1

  • Property Information

    SQ ft (Living Area): 4,014 View: Ocean View,Open Water View Subdivision: Plant Beach (87.5) Stories: 3 Stories

  • Listing Price Information

    List Price: $3,995,000

  • Tax Information

    Taxes: $23,896 Tax Year: 2025 Parcel Number: 00415170000000 Tax Exemptions: None

  • Virtual Tour

    Virtual Tour (External Link)

  • Multi-Unit Information

    Pets Allowed: Pets Allowed

  • Homeowners Association Information

    Mandatory Home Owners Asc: No 1st Right of Refusal: No Association Fee: $0.00

  • Utility Information

    FKAA,Municipal Sewer
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
1101 Mastic Street, Islamorada, FL, 33036 $6,999,000 8 6 3,649 3,649 SqFt
88110 Overseas Hwy, Islamorada, FL, 33036 $6,999,000 4 5 2,797 2,797 SqFt
102 Anglers Way, Islamorada, FL, 33036 $1,150,000 2 3 1,376 1,376 SqFt
109 Columbus Dr, Islamorada, FL, 33036 $6,700,000 4 5 --
88351 Old Highway HIGHWAY, Islamorada, FL, 33036 $14,990,000 6 9 7,590 7,590 SqFt
87895 Old Highway HIGHWAY, Islamorada, FL, 33036 $24,995,000 5 8 9,011 9,011 SqFt
87950 Overseas Highway .., Islamorada, FL, 33036 $3,800,000 5 3 2,464 2,464 SqFt
87429 Old Highway HIGHWAY, Islamorada, FL, 33036 $18,999,000 6 8 6,692 6,692 SqFt
87429 Old Highway, Islamorada, FL, 33036 $18,999,000 6 6 6,054 6,054 SqFt
316 North Drive DRIVE, Islamorada, FL, 33036 $2,400,000 3 4 2,309 2,309 SqFt

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ByOwner last updated this listing 08/17/2026 @ 23:28

MLS: 620430 LISTED BY: Cheri Tindall , Ocean Sotheby's International Realty 305-712-8888 SOURCE: Florida Keys MLS, Inc.

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