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Land with Home for Sale in Plantation Key, Florida

139 Gimpy Gulch Dr, Plantation Key, FL 33036

$13,900,000
3.2 acres
Active sale
$1m drop
Est $78,705/mo

Yes, you can have it all! This one-of-a-kind 3.2 acre Islamorada bayfront estate offers a new boat dock, more than 250 feet of sandy wade-in bayfront shoreline, two full residences, a separate garage/media house and a move-in ready package of extras unlike any other property in the Keys. This remarkable compound captures the spirit of the Keys with a level of scale and exclusivity seldom found on the islands. Arrive through a private gate to discover a secluded retreat where every detail has been curated for relaxed coastal living. For boaters, the new boat dock offers immediate access to Florida Bay and immediate Atlantic Ocean access through nearby Snake Creek. The welcome package also includes a newer 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 full 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 encompasses 2 acres of upland, 1.2 acres of baybottom, a separate buildable 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 retreat.

6,573
Sq feet
6
Beds
6
Full baths
3
1/2 baths
2014
Built

Location

Street address
139 Gimpy Gulch Dr
Zip code
33036
Community
Misc Plantation Key (85.0)
Elevation
3 feet
Coordinates
24.9619, -80.5707

Directions

Gated - no access without making an appointment with the listing agent. Proof of funds required. Plantation Key bayside mm 87. Driveway is between Rain Barrel and Founder's Park.

Property details

Acreage
3.2 acres
Zoning
R1 - Residential Single F
MLS #
FLKEYSMLS 620077
Posted

Property taxes

2025
$92,231

Parcels

  • 00091852-000000

Legal description

Details and features

Listing

Type
Residential
Subtype
Single Family Residence

Lot

View
Water
Waterfront
Yes

Exterior

Parking
Open
Fencing
Fenced
Pool
Patio, Porch
Structures
Gazebo, Outdoor Kitchen, Storage
Features
Bar, Built-In Grill, Chickee Hut, Detached Guest QTRS, Fencing, Fruit Tree(s), Lighting, Outdoor Shower, Sandy Beach, Sprinkler System

Structure

Heating
Electric
Cooling
Central Air
Materials
CBS, Combo Construction
Roof
Metal

Interior

Rooms
Bathroom x 9, Bedroom x 6, Exercise Room, Game Room
Flooring
Tile
Appliances
Dishwasher, Dryer, Microwave, More Appliances, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer
Security
Security System
Features
Gym, Media Room

Listing history

DateEventPriceChangeSource
Aug 2, 2026Price drop$13,900,000$1,000,000 -6.7%FLKEYSMLS
May 30, 2026New listing$14,900,000FLKEYSMLS
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This 3.2-acre property is located at 139 Gimpy Gulch Dr in Plantation Key, FL 33036. The property is available for sale, priced at $13,900,000. It has a 6,573 square foot 6-bedroom, 7.5-bath house built in 2014.

Listed by Coldwell Banker Schmitt Islamorada, (305) 664-4470

Checked 1 hour agoUpdated Source

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