87445 Old Highway, Plantation Key, FL 33036
Local realty services provided by:Better Homes and Gardens Real Estate Destinations
Listed by: cheri tindall, leslie leopold
Office: ocean sotheby's international realty
MLS#:620430
Source:FL_FKBOR
Price summary
- Price:$3,995,000
- Price per sq. ft.:$995.27
About this home
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....
Contact an agent
Home facts
- Year built:1999
- Listing ID #:620430
- Added:2 day(s) ago
- Updated:June 29, 2026 at 02:59 PM
Rooms and interior
- Bedrooms:5
- Total bathrooms:4
- Kitchen Description:Quartz Countertops
- Living area:4,014 sq. ft.
Heating and cooling
- Cooling:Ceiling Fans(s), Central Air
- Heating:Central, Electric
Structure and exterior
- Year built:1999
- Building area:4,014 sq. ft.
- Lot area:1.82 Acres
- Construction Materials:Concrete
- Exterior Features:Privacy Wall/Fence
Finances and disclosures
- Price:$3,995,000
- Price per sq. ft.:$995.27
- Tax amount:$23,895
Features and amenities
- Amenities:Drapes Included, Window Treatments
Parking
- Parking description:Carport, Covered, Off Street
New listings near 87445 Old Highway
- New
$3,875,000Active4 beds 3 baths3,088 sq. ft.109 Giardino Drive, Plantation Key, FL 33036
MLS# 620412Listed by: COLDWELL BANKER SCHMITT ISLAMORADA - New
$2,999,000Active3 beds 4 baths3,817 sq. ft.111 Spoonbill Road, Plantation Key, FL 33070
MLS# 620411Listed by: LOKATION REAL ESTATE - POMPANO BEACH - New
$1,250,000Active2 beds 2 baths1,055 sq. ft.182 Airstream Lane, Plantation Key, FL 33070
MLS# 620396Listed by: BERKSHIRE HATHAWAY HOMESERVICES KEYS REAL ESTATE - ISLAMORADA - New
$599,000Active2 beds 2 baths1,352 sq. ft.87200 Overseas Highway #D3, Plantation Key, FL 33036
MLS# 620393Listed by: BERKSHIRE HATHAWAY HOMESERVICES KEYS REAL ESTATE - ISLAMORADA
$2,399,000Active4 beds 4 baths2,409 sq. ft.127 & 121 Monroe Drive #1-3, Plantation Key, FL 33070
MLS# 620278Listed by: LOKATION REAL ESTATE - POMPANO BEACH
$629,000Active2 beds 2 baths1,337 sq. ft.87200 Overseas Highway #APT A 7, Plantation Key, FL 33036
MLS# 620243Listed by: EXP REALTY, LLC
$685,000Active3 beds 2 baths1,352 sq. ft.87200 Overseas Highway #K5, Plantation Key, FL 33036
MLS# 620241Listed by: EXP REALTY, LLC
$299,000Active2 beds 2 baths989 sq. ft.87455 Old Highway #235, Plantation Key, FL 33036
MLS# 620217Listed by: BERKSHIRE HATHAWAY HOMESERVICES KEYS REAL ESTATE - ISLAMORADA
$629,000Active2 beds 2 baths1,337 sq. ft.87200 Overseas Hwy A7 #A7, Plantation Key, FL 33036
MLS# A12006598Listed by: COMPASS FLORIDA, LLC