87445 Old Highway, Plantation Key, FL 33036 (MLS# 620430)

87445 Old Highway, Plantation Key, FL 33036

$3,995,000

Virtual Tour

https://bcove.video/3CinzzY

Property Type: Residential Bedrooms: 5 Baths: 4 Square Footage: 4,014 Lot Size (sq. ft.): 79,399 Status: Pending

Current Price: $3,995,000 List Date: 6/27/2026 Last Modified: 8/18/2026

Overview

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 breat ... (Read more)

Listing Details MLS# 620430

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

Contract Information

Listing Board: Florida Keys
As is Rght to Inspct: Yes
Species List: Yes

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

Status Change Info

Under Contract Date: 2026-08-18
Contingent: Contingent/Show

Association Info

Mandatory Home Owners Asc: No
1st Right of Refusal: No

Building Style

Above Flood: Unknown
# Stories: 3 Stories

More Information

Pool Info

Heated: Yes

Financial Status

Standard Sale: Yes

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: August - 18 - 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.