3 Total Photos [Click to View All]

139 Gimpy Gulch Drive

Islamorada, FL

Listing Details

  • $14,900,000
  • MLS# 620077
  • Type Residential - Single Family
  • Status Active
  • 6
    Bedrooms
  • 6 full 3 partial
    Bathrooms
  • 6,573
    Square Feet
  • 3.200 acres
    Lot Size
  • 2014
    Year Built

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. For boaters, a new boat dock offers immediate access to Florida Bay and immediate Atlantic Ocean access... Read more 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 estates 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, its 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 Islamoradas crown jewel Founders 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.

Key Features

  • Community Boat Ramp
View All Features
139 Gimpy Gulch Drive
Islamorada, FL 33036
Subdivision
Misc Plantation Key (850)
County
Monroe

Contact the Agent

Luxury Homes Specialist
Contact the Listing Agent
Real estate agents ready to serve you | Browse homes and real estate for sale
Illustrated Properties is an exclusive member of Forbes Global Properties in Miami-Dade County, Broward County, Palm Beach County, Martin County, Lee County, and Monroe County. Forbes® is a registered trademark used under license.

Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 06/22/2026. The listing information on this page last changed on 06/22/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Mon 06/22/2026 12:00:03 AM EST) or Miami MLS (last updated Sun 06/21/2026 11:48:33 PM EST) or Stellar MLS (last updated Sun 06/21/2026 11:44:10 PM EST) or SPC MLS (last updated Sun 06/21/2026 11:21:13 PM EST) or Martin MLS (last updated Sun 06/21/2026 11:38:10 PM EST) or Indian River MLS (last updated Sun 06/21/2026 11:30:12 PM EST) or Northeast Florida MLS (last updated Sun 06/21/2026 11:58:52 PM EST) or Beaches MLS (last updated Sun 06/21/2026 2:37:37 AM EST) or Naples MLS (last updated Sun 06/21/2026 11:40:22 PM EST) or PBI MLS (last updated Sun 06/21/2026 11:21:27 PM EST) or Florida Keys MLS (last updated Sun 06/21/2026 8:29:36 PM EST). Real estate listings held by brokerage firms other than Illustrated Properties may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
Privacy Policy / DMCA Notice / ADA Accessibility
Federal Housing Equal Opportunity Realtor
This site is hosted, designed and copyright © 1994 - 2026 by Delta Media Group, Inc. -- Patent Pending --

All Property Features

  • Property Type: Residential - Single Family
  • Add. Parcel #1: 00091880-000200
  • Appliances: More Appliances, Stainless Steel Appliance(s), Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer, Washer
  • Building Above Flood: Yes
  • Community Features: Community Boat Ramp
  • Cooling: Central Air
  • Days on Site: 23
  • Dock: Wood
  • Dockage: Boat Ramp
  • Dock Length: 100
  • Exterior: CBS, Combo Construction
  • Exterior: Bar, Storage, Sprinkler System, Sandy Beach, Outdoor Shower, Outdoor Kitchen, Lighting, Detached Guest Qtrs, Gazebo, Fruit Tree(s), Fencing, Chickee Hut, Built-in Grill
  • Flood Zone: VE, AE,0.2 PCT ANN
  • Flooring: Tile
  • Furnished: Yes
  • Furnished: Furnished
  • Garage: 2
  • Heating: Electric
  • HOA (1st Right of Refusal) Y/N: No
  • HOA (Mandatory) Y/N: No
  • Interior: Split Bedroom, Security System, Storage, Entrance Foyer, Pantry
  • Key/Island: Plantation Key
  • Listing Board: Florida Keys
  • Lot Dimensions: 3.20Acre(s)
  • Lot Size: 3.20 Acres
  • Off Shore Island: No
  • Parcel #: 00091852-000000
  • Parking: Garage, Trailer Storage, Covered Parking, Off Street Parking, Guest Parking, Open Parking
  • Parking Space(s): 2
  • Pets: Pets Allowed
  • Pool: In Ground, Concrete
  • Porch/Balcony: Open Porch/Balcony, Patio
  • Property Condition: Updated/Remodeled
  • Roof Type: Metal Roof
  • Security: yes
  • Security: Electric Gate, On Premises System
  • Sewer Hookup: Yes
  • Specialty Rooms: Gym, Media Room
  • Swimming Pool: Yes
  • Taxes: $92,230
  • Tax exemptions: None
  • Utilities: FKAA, Propane, Elect Separate Meter, Water Separate Meter, Whole House Generatr
  • Waterfront: Bay Front, Open Water, Gulf Front
  • Waterview: Bay/Gulf View, Open Water View
  • Windows/Doors: Impact Rstnce Window, Impact Rstnce Doors
  • Year Built: 2014
  • Zoning: R1 - Residential Single Family

Schedule a Showing

Complete the form below to see 139 Gimpy Gulch Drive, Islamorada, FL 33036. An agent will get in touch to confirm your request shortly.

Choose your video chat app
Request a Showing