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© 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

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+20

150 List Street

Upper Matecumbe Key Islamorada, FL, 33036

Active

$4,900,000

150 List Street

Upper Matecumbe Key Islamorada, FL, 33036

Active

$4,900,000

1

Bedrooms

1

Bathrooms

946 sqft

Living Area

1950

Year Built

$4,900,000Tour 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.

34,000

Lot Size (sqft)

138

Days on Market

Dock Score™

DockOnly
58
Fair

What shaped this score

✓Bay Front
✓Dock with boat lift for up to 33ft
✓Bridge-free to bay
✓Fits boats up to ~30ft (est.)

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

Dock & Water AccessMLS

Bay FrontGulf FrontOpen Water📝 20K-lb boat lift

AI Aerial Imagery Detection

Dock Detected

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 an extraordinary opportunity to own 34,000 square feet of prime bayfront real estate in one of Islamorada's most coveted and private enclaves. Boasting 100+ feet of pristine bay frontage, this exceptional property captures open water views, serene sunsets, and the essence of the Florida Keys lifestyle. Tucked within the property is a charming ground level 1950s cottage offering one bedroom and one bathroom - ideal as a weekend escape, guest retreat, or comfortable interim residence while you bring your custom waterfront vision to life. For boating enthusiasts, the estate offers dockage with direct bay access, placing world-class fishing, sandbars, and crystal-clear waters just moments away. A permit has been submitted to repair and expand the existing dock and add two boat lifts (20,000 lb and 16,000 lb), significantly enhancing the property's boating capabilities and long-term value. Surrounded by multimillion-dollar estate home sales, this offering represents a rare chance to secure a premier bayfront parcel in one of Islamorada's most sought-after locations. With the existing estate slated for demolition and redevelopment, the conceptual renderings unveil a spectacular 4,872-square-foot custom residence offering five bedrooms, five and a half bathrooms, a three-car garage, and a resort style pool - all thoughtfully designed to capture water views from every vantage point. This vision blends refined indoor living with outdoor elegance, creating a seamless waterfront sanctuary. Whether you envision a private coastal retreat or an entertainer's paradise, this remarkable bayfront estate offers endless possibilities in an unparalleled setting.

Schedule a Showing

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

Select a date

Location

Upper Matecumbe Key Islamorada, 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: 6/15/2026

© 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
58
Fair

What shaped this score

✓Bay Front
✓Dock with boat lift for up to 33ft
✓Bridge-free to bay
✓Fits boats up to ~30ft (est.)

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: 7ft

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%

$980,000 down

%
Principal & Interest$25,425/mo
Property Tax (est. ~1.2%, varies by county)$4,900/mo
Home Insurance (est.)$250/mo
Total Monthly Payment$30,575
Loan Amount: $3,920,000Rate: 6.75%
Get Pre-Qualified

Estimated payments only. Actual rates and terms may vary.

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