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Anchor Line Realty

Anchor Line Realty specializes in buyer brokerage, real estate sales listings, and long term property management in Key West & the Florida Keys.

Call: (305) 766-6835

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$3,700,000
87445 Old Highway
Plantation Key, FL 33036
MLS# 620430
Status: Closed
5 beds  |  4 baths  |  4014 sqft

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87445 Old Hwy
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87445 Old Hwy Pool Beautiful setting Beach and observation pier Palm lined property Spacious home with inviting pool Porch/Balcony 2nd level balcony Relaxing views Street view Observation pier 1.8 oceanfront acres Foyer Sweeping staircase Quartz countertops Stainless steel appliances Views from every room Living room 1st floor bedroom #1 1st floor bath #1 1st floor bedroom #2 1st floor bath #2 Staircase to 3rd level 3rd level sitting room Primary bedroom Spacious En suite bath Guest bedroom #3 Private balcony Guest bedroom #4 3rd floor guest bath 3rd level balcony Beach room off the pool

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.

Details
Maps
Contract Information
Current Price: $3,700,000
Listing Date: 2026-06-26
Listing Board: Florida Keys
Leased Price Monthly: $3,700,000
As is Rght to Inspct: Yes
Species List: Yes
Location, Tax & Legal
Street #: 87445
Street Name: Old
Street Suffix: Highway
Key/Island: Plantation Key
State/Province: FL
Zip Code: 33036
County: Monroe
Subdivision: Plant Beach (87.5)
Area: 25 - Plantation Key
General Property Description
Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: Yes
Control Depth: 3
Pool: Yes
Year Built: 1999
Lot SqFt: 79399
Lot Sqft Source: Property Data Card
Acres: 1.82
Living Apx SqFt: 4014
SqFt Source: Seller
Total Bedrooms: 5
Full Baths: 4
Total Baths: 4
Rentals Allowed: Yes
Min Rental Days: 7
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Building Style
Above Flood: Unknown
# Stories: 3 Stories
Pool Info
Heated: Yes
Financial Status
Standard Sale: Yes
Status Change Info
Under Contract Date: 2026-08-18
Leased Date: 2026-10-01
Leased Price Monthly: $3,700,000
Status: Closed
Property Features
Fee Includes: None
Tax Exemptions: None
Waterfront: Oceanfront; Open Water
Waterview: Ocean View; Open Water View
Dockage: Other Dockage
Vehicle Storage: Garage; Carport; Covered Parking; Off Street Parking
Furnished: Negotiable
Cooling: Ceiling Fans(s); Central Air
Heating: Central
Utilities: FKAA; Municipal Sewer
Interior Features: Drapes/Blinds Incl; Entrance Foyer; Quartz Countertops; Split Bedroom; Window Treatments
Pre-Wired: Cable
Appliances: Dishwasher; Dryer; Microwave; More Appliances; Oven; Refrigerator; Stainless Steel Appliance(s); Washer
Exterior Features: Privacy Wall/Fence
Pool Info: In Ground; Salt Water
Construction: CBS; Concrete
Shutters: Accordion
Floor: Tile
Roof: Metal Roof
Pets: Pets Allowed
Security: Electric Gate; Patrolled Area
Land Size: 1 Less Than 2 Acres
Title: Title Ins - Buyer

Listing Office: Ocean Sotheby's International Realty

Last Updated: October - 01 - 2026

The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.


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David Austin, Owner/Broker
Anchor Line Realty, LLC
820 Ashe Street
Key West, FL 33040
www.anchorlinerealty.com
[email protected]
305.766.6835
Member, National Association of Realtors (NAR)
Member, Florida Association of Realtors (FAR)
Member, Key West Association of Realtors (KWAR)