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$14,900,000
Plantation Key, FL 33036
MLS# 620077
6 beds | 10 baths | 6573 sqft
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1 / 120
Property 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.
Details
Maps
Contract Information
Listing Board: Florida Keys
As is Rght to Inspct: Yes
Species List: No
Current Price: $14,900,000
Listing Date: 2026-05-29
List Price: $14,900,000
Location, Tax & Legal
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
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
Waterfront: Yes
Control Depth: 4
Lot Size: 252 ft wide
Lot SqFt: 139392
Pool: Yes
Lot Sqft Source: Tax Records
Total Units: 0
Acres: 3.2
SqFt Source: Tax Records
Rentals Allowed: With Restrictions
Min Rental Days: 28
Style: Single Family
Year Built: 2014
Living Apx SqFt: 6573
Total Bedrooms: 6
Full Baths: 7
Half Baths: 3
Total Baths: 10
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. 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.
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.
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0
Fee Includes
None: 1
Dockage
Dock Length: 100
Dock: Wood
Boat Ramp: 1
Tax Exemptions
None: 1
Appliances
Dishwasher: 1
Dryer: 1
Microwave: 1
More Appliances: 1
Oven: 1
Range: 1
Refrigerator: 1
Stainless Steel Appliance(s): 1
Washer: 1
Pets
Pets Allowed: 1
Cooling
Central Air: 1
Heating
Electric: 1
Waterfront
Bay Front: 1
Gulf Front: 1
Open Water: 1
Waterview
Bay/Gulf View: 1
Open Water View: 1
Floor
Tile: 1
Neighborhood Feature
Community Boat Ramp: 1
Interior Features
Entrance Foyer: 1
Pantry: 1
Security System: 1
Split Bedroom: 1
Storage: 1
Property Condition
Updated/Remodeled: 1
Specialty Rooms
Guest/Servant Qtrs: Legal
Gym: 1
Media Room: 1
Building Style
Above Flood: Yes
Windows/Doors
Impact Rstnce Doors: 1
Impact Rstnce Window: 1
Vehicle Storage
Garage: 1
Open Parking: 1
Security
Electric Gate: 1
On Premises System: 1
Construction
CBS: 1
Combo Construction: 1
Land Size
2 Less Than 5 Acres: 1
Furnished
Furnished: 1
Utilities
Elect Separate Meter: 1
FKAA: 1
Propane: 1
Water Separate Meter: 1
Whole House Generatr: 1
Porch/Balcony
Open Porch/Balcony: 1
Patio: 1
Title
Title Ins - Buyer: 1
Exterior Features
Bar: 1
Built-in Grill: 1
Chickee Hut: 1
Detached Guest Qtrs: 1
Fencing: 1
Fruit Tree(s): 1
Gazebo: 1
Lighting: 1
Outdoor Kitchen: 1
Outdoor Shower: 1
Sandy Beach: 1
Sprinkler System: 1
Storage: 1
Pool Info
In Ground: 1
Heated: Yes
Concrete: 1
Dimensions: 100 feet long
Pre-Wired
Cable: 1
Roof
Metal Roof: 1
Status Change Info
Status: Active
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.