DockOnly™

The only MLS search built exclusively for boaters. Find your dock home.

Company

  • About
  • Contact
  • Blog

Search

  • By City
  • By County
  • Dockominiums

Services

  • Marine Services
  • Dock Builders
  • Find Contractors

For Agents

  • Become a Partner
  • Referral Program
  • Featured Listings

Legal

  • Privacy Policy
  • Terms of Use
  • MLS Compliance

© 2026 DockOnly™. All rights reserved.

DockOnly™ and Dock Score™ are trademarks of Blue Mar Real Estate Group Inc.

Blue Mar Real Estate Group Inc., Licensed Florida Real Estate Broker

Blue Mar Real Estate Group Inc.

Licensed Florida Real Estate Broker · DBPR License CQ1018554

4000 Ponce De Leon Blvd, Suite 470, Coral Gables, FL 33146

[email protected]

Listing data is provided by participating Multiple Listing Services and is deemed reliable but not guaranteed. Each listing's MLS source and its required disclosures appear with that listing. Dock Score™ is a DockOnly.com rating and is not provided by or affiliated with any MLS or listing broker. NOAA chart data is public domain and for reference only, not for navigation. Full MLS Compliance

DockOnly and Blue Mar Real Estate Group are committed to ensuring digital accessibility for individuals with disabilities. We are continuously working to improve the accessibility of our web experience for everyone, and we welcome feedback and accommodation requests. If you wish to report an issue or seek an accommodation, please let us know.

Equal Housing OpportunityEqual Housing Opportunity

This website complies with the Fair Housing Act. We do not discriminate on the basis of race, color, religion, sex, national origin, familial status, or disability.

DockOnly™Blue Mar Real Estate Group Inc., Licensed Florida Real Estate BrokerBlue MarREAL ESTATE GROUPBlue Mar Real Estate Group Inc., Licensed Florida Real Estate Broker
SearchMarketsDockominiums
SearchMarketsDockominiumsSaved
Real Estate Agents
Home
SearchSaved
Back to Search
87445 Old Highway photo 1
87445 Old Highway photo 2
87445 Old Highway photo 3
87445 Old Highway photo 4
87445 Old Highway photo 5
87445 Old Highway photo 6
87445 Old Highway photo 7
87445 Old Highway photo 8
87445 Old Highway photo 9
87445 Old Highway photo 10
87445 Old Highway photo 11
87445 Old Highway photo 12
87445 Old Highway photo 13
87445 Old Highway photo 14
87445 Old Highway photo 15
87445 Old Highway photo 16
87445 Old Highway photo 17
87445 Old Highway photo 18
87445 Old Highway photo 19
87445 Old Highway photo 20
87445 Old Highway photo 21
87445 Old Highway photo 22
87445 Old Highway photo 23
87445 Old Highway photo 24
87445 Old Highway photo 25
1 / 25
87445 Old Highway
25 photos
87445 Old Highway photo 2
87445 Old Highway photo 3
87445 Old Highway photo 4
87445 Old Highway photo 5
+20

87445 Old Highway

Plantation Key, FL, 33036

Active

$3,995,000

87445 Old Highway

Plantation Key, FL, 33036

Active

$3,995,000

5

Bedrooms

4

Bathrooms

4,014 sqft

Living Area

1999

Year Built

$3,995,000Tour the dockSchedule a Showing
Navigation note: Navigation routes show the shortest mapped path to open water. A vessel taller than the binding bridge clearance may still reach open water via a longer alternate route that we don't currently map. Verify navigability with a local captain or surveyor before relying on it.

79,399

Lot Size (sqft)

24

Days on Market

Dock Score™

DockOnly
65
Good

What shaped this score

✓Ocean Access
✓Fits boats up to ~100ft+ (est.)
✓Bridge-free to bay
✓Dock present
·Draft not independently verified
Est. waterfront~225 ft

DockOnly.com rating, not provided by the MLS or listing broker.

Dock & Water AccessMLS

OceanfrontOpen Water

AI Aerial Imagery Detection

Dock DetectedDeep Water Indicators

Detected by AI from open-source aerial mapping imagery and may not reflect current conditions. This information was not provided by the MLS or listing broker. Always verify dock infrastructure with the listing agent.

Navigation RouteDockOnly

Data sources: SFWMD AHED waterway polygons · FHWA National Bridge Inventory 2024 · Not provided by the MLS or listing broker.

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.

Schedule a Showing

See the property and tour the dock. A licensed waterfront specialist will arrange your private showing.

Select a date

Location

Plantation Key, FL, 33036

No price history available for this property.

Displayed by Blue Mar Real Estate Group Inc., Licensed Florida Real Estate Broker (DBPR CQ1018554) · [email protected]

Listing courtesy of Ocean Sotheby's International Realty via Florida Keys MLS

Last updated: 6/27/2026

© 2026 Florida Keys Board of REALTORS®, Inc. All rights reserved. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange (IDX) program of the Florida Keys Board of REALTORS®. Information is deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change, or withdrawal.

IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Dock Score™

DockOnly
65
Good

What shaped this score

✓Ocean Access
✓Fits boats up to ~100ft+ (est.)
✓Bridge-free to bay
✓Dock present
·Draft not independently verified
Est. waterfront~225 ft

DockOnly.com rating, not provided by the MLS or listing broker.

Nearest Bridge Clearances

Florida Keys, critical for tall/large vessels

No bridge data available for this location.
FEMA Flood Zone AE
BFE: 10ft

Special Flood Hazard Area

View FEMA Flood Map →
Loading nearby marinas…
Loading nearby sandbars…

Mortgage Calculator

Estimate your monthly payment for this waterfront property

20%

$799,000 down

%
Principal & Interest$20,729/mo
Property Tax (est. ~1.2%, varies by county)$3,995/mo
Home Insurance (est.)$250/mo
Total Monthly Payment$24,974
Loan Amount: $3,196,000Rate: 6.75%
Get Pre-Qualified

Estimated payments only. Actual rates and terms may vary.

Similar Listings

1557 Long Beach Dr$3,899,000

1557 Long Beach Dr

Big Pine, FL

6 7 3,029 sqft

Courtesy of Keller Williams Miami Portfolio Collection via Florida Keys MLS

145 Venetian Drive$3,350,000

145 Venetian Drive

Islamorada, FL

4 4 3,182 sqft

Courtesy of Langley Knight Gardner Islamorada via MIAMI REALTORS®

74049 Overseas$3,999,999

74049 Overseas

Islamorada, FL

4 4 2,591 sqft

Courtesy of Paradise Florida Keys Real Estate, a Luxury Brand via Florida Keys MLS

188 Orange Blossom Rd$3,499,999

188 Orange Blossom Rd

Tavernier, FL

3 3 2,130 sqft

Courtesy of MDZ Realty, LLC. via MIAMI REALTORS®

397 Laguna Avenue$3,339,000

397 Laguna Avenue

Key Largo, FL

7 5 2,992 sqft

Courtesy of London Foster Realty via MIAMI REALTORS®

231 E Shore Drive Unit 2$4,250,000

231 E Shore Drive Unit 2

Key West, FL

5 6 4,103 sqft

Courtesy of Serhant via MIAMI REALTORS®

Swipe or use arrows to see more