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139 Gimpy Gulch Drive DRIVE

Islamorada, FL 33036

$14,900,000 $62,819/Mo

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Overview

Bed

Bath

6,573

Sqft

Description

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 the bay and ocean and the included neighboring lot provides convenient boat ramp access. This one-of-kind package also includes a 34' Edgewater with twin 400 hp Yahamas, a pair of Waverunners and U TV tow vehicle, plus fishing rods, kayaks, paddle boards, and bicycles to enjoy everything Islamorada has to offer. The resort-style pool and 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 a main home with ground level living, a tri-level guest home, and a large garage/media house all with classic island character. Both residences 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, furnishings, 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 Details

Property Type : Residential - Single Family

Price : $14,900,000

AD Id : 79496050

MLS Id : 620077

Beds : 6

Living Area Size : 6,573

Year Built : 2014

County : Monroe

Map

What's Nearby

Nearby Areas

Features

Bedroom Information

Total Bedrooms: 6 Gym,Media Room

Bathroom Information

Total Baths: 9 Full Baths: 6 Half Baths: 3
Interior Features

Split Bedroom,Security System,Storage,Entrance Foyer,Pantry Appliances: More Appliances,Stainless Steel Appliance(s),Microwave,Oven,Range,Refrigerator,Dishwasher,Dryer,Washer
Roofing Information

Metal Roof

Flooring Information

Tile

Heating & Cooling

Cooling: Central Air Heating: Electric Water Front: Yes Bay Front,Open Water,Gulf Front Bay/Gulf View,Open Water View

Window Information

Window Treatments: Impact Rstnce Window,Impact Rstnce Doors

Building Information

Year Built: 2014 Total Units: 0.00 Floor Location: 139392 Construction: CBS,Combo Construction Security System: Electric Gate,On Premises System Roof: Metal Roof
Exterior Features

Bar,Storage,Sprinkler System,Sandy Beach,Outdoor Shower,Outdoor Kitchen,Lighting,Detached Guest Qtrs,Gazebo,Fruit Tree(s),Fencing,Chickee Hut,Built-in Grill

Pool Information

In Ground,Concrete Heated: Yes Dimensions: 100 feet long
Guest House Information

Legal

Lot Information

Lot Dimensions: 252 ft wide Lot SqFt: 139,392 Lot SqFt Source: Tax Records 13 63 37 PLANTATION KEY PT GOVT LOT 1 AND ADJ BAY BTM G32-114 (see deed)
Property Information

SQ ft (Living Area): 6,573 View: Bay/Gulf View,Open Water View Subdivision: Misc Plantation Key (85.0)

Listing Price Information

List Price: $14,900,000

Tax Information

Taxes: $92,231 Tax Year: 2025 Parcel Number: 00091852-000000 Tax Exemptions: None

Virtual Tour

Virtual Tour (External Link)
Multi-Unit Information

Pets Allowed: Pets Allowed
Homeowners Association Information

Mandatory Home Owners Asc: No 1st Right of Refusal: No Association Fee: $0.00

Utility Information

FKAA,Propane,Elect Separate Meter,Water Separate Meter,Whole House Generatr

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Nearby Home Value

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82719 Old Hwy, Islamorada, FL, 33036	$24,995,000	7	11	10,182	10,182 SqFt
122 Court Contessa, Islamorada, FL, 33036	$2,795,000	3	3	2,374	2,374 SqFt
111 Anglers Way, Islamorada, FL, 33036	$1,199,990	2	3	1,376	1,376 SqFt
109 Columbus Dr, Islamorada, FL, 33036	$6,700,000	4	5	--
164 Venetian Dr, Islamorada, FL, 33036	$1,599,000	4	2	1,680	1,680 SqFt
166 Bayview Drive, Islamorada, FL, 33036	$4,700,000	4	4	--
Residential, Islamorada, FL, 33036	$2,649,000	3	4	1,768	1,768 SqFt
20 Avacado St, Islamorada, FL, 33036	$15,950,000	6	7	6,680	6,680 SqFt
145 Venetian Drive, Islamorada, FL, 33036	$3,350,000	4	4	3,182	3,182 SqFt
162 Bayview Dr, Islamorada, FL, 33036	$8,950,000	8	10	5,392	5,392 SqFt