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Active$14,900,000
Plantation Key, FL, 33036
Active$14,900,000
6
Bedrooms
9
Bathrooms
6,573 sqft
Living Area
2014
Year Built
139,392
Lot Size (sqft)
52
Days on Market
Dock Score™
DockOnlyWhat shaped this score
DockOnly.com rating, not provided by the MLS or listing broker.
AI Aerial Imagery Detection
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.
Data sources: SFWMD AHED waterway polygons · FHWA National Bridge Inventory 2024 · Not provided by the MLS or listing broker.
Yes, you can have it all! Tucked away behind mature tropical landscaping and stretching across an expanse of more than 250 feet of sandy bayfront shoreline, 139 Gimpy Gulch is a rare Islamorada estate designed for those who value privacy, boating, sunsets and effortless luxury in equal measure. This one-of-a-kind compound captures the spirit of the Keys with a level of scale and exclusivity seldom found on the islands. Arrive through private gates to discover a secluded retreat where every detail has been curated for relaxed coastal living. For boaters, a new boat dock offers immediate access to Florida Bay and immediate Atlantic Ocean access through nearby Snake Creek. This one-of-kind package also includes a 34' Edgewater with twin 400 hp Yahamas, a pair of Waverunners and UTV tow vehicle, plus fishing rods, kayaks, paddle boards, and bicycles to enjoy everything Islamorada has to offer. The 100 ft. long resort-style pool with large spa create the centerpiece of the property, surrounded by multiple lounging areas, outdoor kitchen with covered bar, shady terraces and intimate gathering spaces. The estate's flexible layout includes two homes--a 2/2.5 with ground level living, and a 3/3.5 tri-level--plus a 1/1.5 media house with 2-car garage, all with classic island character. Both homes offer chef kitchens with high-end appliances including SubZero and La Cornue. Not only is this estate ready for fun, it's also ready to enjoy with furniture, decor, kitchenware and even linens included! This remarkable property includes 2 acres of upland, 1.2 acres of baybottom, the separate vacant lot plus valuable development rights. It is also conveniently located next to Islamorada's crown jewel Founder's Park for near instant access to seasonal festivals, sports fields, dog park, playground, tennis and pickleball courts and much more. All of these features elevate the property into a true legacy holding--ideal as a luxury residence, family compound, or private bayfront retreat.
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Plantation Key, FL, 33036
Displayed by Blue Mar Real Estate Group Inc., Licensed Florida Real Estate Broker (DBPR CQ1018554) · [email protected]
Listing courtesy of Coldwell Banker Schmitt Islamorada via Florida Keys MLS
Last updated: 7/1/2026
© 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™
DockOnlyWhat shaped this score
DockOnly.com rating, not provided by the MLS or listing broker.
Nearest Bridge Clearances
Florida Keys, critical for tall/large vessels
Estimate your monthly payment for this waterfront property
$2,980,000 down
Estimated payments only. Actual rates and terms may vary.