139 Gimpy Gulch Drive, Plantation Key, FL 33036

New Listing

$14,900,000

Virtual Tour

https://youtu.be/cm9MFf7HL4M

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

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.

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