139 Gimpy Gulch Drive, Plantation Key, FL 33036
Local realty services provided by:CENTURY 21 Circle
139 Gimpy Gulch Drive,Plantation Key, FL 33036
$14,900,000
- 6 Beds
- 9 Baths
- 6,573 sq. ft.
- Single family
- Active
Listed by: brett newman
Office: coldwell banker schmitt islamorada
MLS#:620077
Source:FL_FKBOR
Price summary
- Price:$14,900,000
- Price per sq. ft.:$2,266.85
About this home

Yes, you can have it all! Tucked behind lush tropical landscaping and stretching across an expanse of more than 250 feet of sandy bayfront shoreline, 139 Gimpy Gulch is a rare Islamorada 3.2-acre 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 Florida Bay and immediate Atlantic Ocean access through nearby Snake Creek. 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 100 ft. long resort-style pool with large 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 two homes--a 2/2.5 with ground level living, and a 3/3.5 tri-level--plus a 1/1.5 media house with 2-car garage, all with classic island character. Both homes 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, decor, 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 retrea...
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Home facts
- Year built:2014
- Listing ID #:620077
- Added:61 day(s) ago
- Updated:July 28, 2026 at 10:48 PM
Rooms and interior
- Bedrooms:6
- Total bathrooms:9
- Kitchen Description:Pantry
- Living area:6,573 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Electric
Structure and exterior
- Year built:2014
- Building area:6,573 sq. ft.
- Lot area:3.2 Acres
- Construction Materials:Combo Construction
- Exterior Features:Bar, Built-in Grill, Chickee Hut, Fencing, Fruit Tree(s), Gazebo, Lighting, Outdoor Kitchen, Outdoor Shower, Sandy Beach, Sprinkler System, Storage
Finances and disclosures
- Price:$14,900,000
- Price per sq. ft.:$2,266.85
- Tax amount:$92,230
Features and amenities
- Amenities:Pantry, Security System, Storage
Parking
- Parking description:Covered, Guest, Off Street, Open
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