139 Gimpy Gulch Drive, Plantation Key, FL 33036
New Listing
$14,900,000
Property Type:
Residential
Bedrooms:
6
Baths:
10
Square Footage:
6,573
Lot Size (sq. ft.):
139,392
Status:
Active
Current Price:
$14,900,000
List Date:
5/29/2026
Last Modified:
5/29/2026
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. 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. For boaters, a new 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 (in indoor storage), a pair of Waverunners and UTV tow vehicle, plus fishing rods, kayaks, paddle boards, and bicycles to enjoy everything Islamorada has to offer. 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.
More Information MLS# 620077
Contract Information
Current Price: $14,900,000
Listing Date: 2026-05-29
Listing Board: Florida Keys
List Price: $14,900,000
As is Rght to Inspct: Yes
Species List: No
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
General Property Description
Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: Yes
Control Depth: 4
Pool: Yes
Year Built: 2014
Lot Size: 252 ft wide
Lot SqFt: 139392
Lot Sqft Source: Tax Records
Acres: 3.2
Living Apx SqFt: 6573
SqFt Source: Tax Records
Total Bedrooms: 6
Full Baths: 7
Half Baths: 3
Total Baths: 10
Rentals Allowed: With Restrictions
Min Rental Days: 28
Status Change Info
Status: Active
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Dockage
Dock Length: 100
Dock: Wood
Building Style
Above Flood: Yes
Specialty Rooms
Guest/Servant Qtrs: Legal
Pool Info
Heated: Yes
Dimensions: 100 feet long
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: May - 29 - 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.
