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139 Gimpy Gulch Drive, Plantation Key, FL 33036

$14,900,000
Property Type: Residential Bedrooms: 6 Baths: 9 Square Footage: 6,573 Lot Size (sq. ft.): 139,392 Status: Active
Current Price: $14,900,000 List Date: 5/29/2026 Last Modified: 6/06/2026

Overview

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 UTV 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 ...

Listing Details MLS# 620077

Location, Tax & Legal

Street #
139
Street Name
Gimpy Gulch
Street Suffix
Drive
Key/Island
Plantation Key
State/Province
FL
Zip Code
33036
County
Monroe
Subdivision
Misc Plantation Key (85.0)
Area
25 - Plantation Key
City
ISLAMORADA
Off Shore Island
No
Mile Marker
87
Marathon Neighborhood
N/A
Senior Community YN
No
Side
Bay/Gulf
Flood Zone
VE,AE,0.2 PCT ANN
Alternate Key #
9100239
Handicap Access
Yes
Add'l Parcel #1
00091880-000200
Parcel #
00091852-000000
Zoning
R1 - Residential Single Family
Deed Restrictions
Unknown
Legal
13 63 37 PLANTATION KEY PT GOVT LOT 1 AND ADJ BAY BTM G32-114 (see deed)
Taxes
92230.77
Tax Year
2025
Pub Sewer HkUp
Yes

Contract Information

Listing Board
Florida Keys
As is Rght to Inspct
Yes
Species List
No

General Property Description

Realtor.COM Type
Residential - Single Family
Style
Single Family
Waterfront
Yes
Control Depth
4
Pool
Yes
Year Built
2014
Lot SqFt
139392
Lot Sqft Source
Tax Records
Acres
3.2
Living Apx SqFt
6573
SqFt Source
Tax Records
Total Bedrooms
6
Full Baths
6
Half Baths
3
Total Baths
9
Rentals Allowed
With Restrictions
Min Rental Days
28
Total Units
0

Association Info

Mandatory Home Owners Asc
No
1st Right of Refusal
No
Association Fee $
0

Dockage

Dock Length
100
Dock
Wood
Boat Ramp
Yes

More Information

Building Style

Above Flood
Yes

Specialty Rooms

Guest/Servant Qtrs
Legal
Gym
Yes
Media Room
Yes

Pool Info

Heated
Yes
Dimensions
100 feet long
In Ground
Yes
Concrete
Yes

Remarks & Misc

Remarks – Consumer
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 UTV 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.
Directions
Gated - no access without making an appointment with the listing agent. Plantation Key bayside mm 87. Driveway is between Rain Barrel and Founder's Park.

Fee Includes

None
Yes

Tax Exemptions

None
Yes

Appliances

Dishwasher
Yes
Dryer
Yes
Microwave
Yes
More Appliances
Yes
Oven
Yes
Range
Yes
Refrigerator
Yes
Stainless Steel Appliance(s)
Yes
Washer
Yes

Pets

Pets Allowed
Yes

Cooling

Central Air
Yes

Heating

Electric
Yes

Waterfront

Bay Front
Yes
Gulf Front
Yes
Open Water
Yes

Waterview

Bay/Gulf View
Yes
Open Water View
Yes

Floor

Tile
Yes

Neighborhood Feature

Community Boat Ramp
Yes

Interior Features

Entrance Foyer
Yes
Pantry
Yes
Security System
Yes
Split Bedroom
Yes
Storage
Yes

Property Condition

Updated/Remodeled
Yes

Windows/Doors

Impact Rstnce Doors
Yes
Impact Rstnce Window
Yes

Vehicle Storage

Garage
Yes
Open Parking
Yes

Security

Electric Gate
Yes
On Premises System
Yes

Construction

CBS
Yes
Combo Construction
Yes

Land Size

2 Less Than 5 Acres
Yes

Furnished

Furnished
Yes

Utilities

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

Porch/Balcony

Open Porch/Balcony
Yes
Patio
Yes

Title

Title Ins - Buyer
Yes

Exterior Features

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

Pre-Wired

Cable
Yes

Roof

Metal Roof
Yes

Property Features

Fee Includes: None Tax Exemptions: None Waterfront: Bay Front; Gulf Front; Open Water Waterview: Bay/Gulf View; Open Water View Dockage: Boat Ramp Property Condition: Updated/Remodeled Vehicle Storage: Garage; Open Parking Furnished: Furnished Cooling: Central Air Utilities: Elect Separate Meter; FKAA; Propane; Water Separate Meter; Whole House Generatr Interior Features: Entrance Foyer; Pantry; Security System; Split Bedroom; Storage Pre-Wired: Cable Specialty Rooms: Gym; Media Room Appliances: Dishwasher; Dryer; Microwave; More Appliances; Oven; Range; Refrigerator; Stainless Steel Appliance(s); Washer Exterior Features: Bar; Built-in Grill; Chickee Hut; Detached Guest Qtrs; Fencing; Fruit Tree(s); Gazebo; Lighting; Outdoor Kitchen; Outdoor Shower; Sandy Beach; Sprinkler System; Storage Pool Info: In Ground; Concrete Construction: CBS; Combo Construction Floor: Tile Roof: Metal Roof Pets: Pets Allowed Neighborhood Feature: Community Boat Ramp Security: Electric Gate; On Premises System Land Size: 2 Less Than 5 Acres Title: Title Ins - Buyer
Listing Office: Coldwell Banker Schmitt Islamorada
Last Updated: June - 06 - 2026
The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.