Ad #7801364
MLS #620077
Yes, you can have it all! Tucked away behind mature tropical
139 Gimpy Gulch Dr, Plantation Key, FL 33036
$14,900,000
6Beds
8Baths
6,573Sqft
3.2Acres
About this property
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.
Property Features
6 Beds
8 Baths
6,573 Sqft
Built in 2014
3.2 Acres
Beachview
On Beachfront
Open
Siding: CBS, Combo Construction
Metal Roof
Has Swimming Pool
Electric (Heating)
$92,231 / yr property tax
Monroe County
Misc Plantation Key (85) Community
Additional Photos
Contact Information
Brett Newman
Coldwell Banker Schmitt Islamorada
305-393-1770
Location
Listing Agent: Brett Newman (License #: 555709) 305-393-1770
Broker: Coldwell Banker Schmitt Islamorada 305-664-4470 Listing Site
Copyright © 2026 Florida Keys Board of REALTORS®. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Broker: Coldwell Banker Schmitt Islamorada 305-664-4470 Listing Site
Copyright © 2026 Florida Keys Board of REALTORS®. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
BeachHouse.com
Printed Aug 11, 2026
Photo Gallery
$14,900,000
6
Beds
8
Baths
6,573
Sqft
139 Gimpy Gulch Dr, Plantation Key, FL 33036
By contacting this agent you agree to these Terms and Conditions.
MLS# 620077
Yes, you can have it all! Tucked away behind mature tropical
$14,900,000
139 Gimpy Gulch Dr, Plantation Key, FL 33036
6
Beds
8
Baths
6,573
Sqft
3.2
Acres
$14,900,000
139 Gimpy Gulch Dr, Plantation Key, FL 33036
6 Beds
8 Baths
6,573 Sqft
3.2 Acres
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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Property Details
HOME DETAILS
6 Beds
8 Baths
6,573 Sqft
Built in 2014
3.2 Acres
BEACH & VIEW
Beachview
On Beachfront
EXTERIOR
Open
Siding: CBS, Combo Construction
Metal Roof
Has Swimming Pool
INTERIOR
Electric (Heating)
FINANCIAL & COMMUNITY
$92,231 / yr property tax
Monroe County
Misc Plantation Key (85) Community
See More Details
Location
Mortgage Calculator
Ad Statistics
Ad Number
7801364
Viewed
93 times
Listing Status
Active
Added
May 29, 2026
Last Refreshed
Jul 03, 2026 06:17:28 PM
Listing Information
Data Source
Florida Keys Board of REALTORS®
Source Property ID
620077
Listing Agent: Brett Newman (License #: 555709) 305-393-1770
Broker: Coldwell Banker Schmitt Islamorada 305-664-4470 Listing Site
Copyright © 2026 Florida Keys Board of REALTORS®. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Broker: Coldwell Banker Schmitt Islamorada 305-664-4470 Listing Site
Copyright © 2026 Florida Keys Board of REALTORS®. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
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