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139 Gimpy Gulch Drive DRIVE

Islamorada, FL 33036
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$14,900,000 $62,819/Mo
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Bed 6

Bed

Bath 9

Bath

SqFt6,573

Sqft

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 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 vehicl e, 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 retreat.

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Detail Ic Property Details

Property Type : Residential - Single Family

Price : $14,900,000

AD Id : 79496050

MLS Id : 620077

Beds : 6

Living Area Size : 6,573

Year Built : 2014

County : Monroe

Subdivision: Waldin Park Estates

  • Map Map

Map

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Feature Features

  • Bedroom Information

    Total Bedrooms: 6 Gym,Media Room

    Bathroom Information

    Total Baths: 9 Full Baths: 6 Half Baths: 3

  • Interior Features

    Split Bedroom,Security System,Storage,Entrance Foyer,Pantry Appliances: More Appliances,Stainless Steel Appliance(s),Microwave,Oven,Range,Refrigerator,Dishwasher,Dryer,Washer

  • Roofing Information

    Metal Roof

    Flooring Information

    Tile

    Heating & Cooling

    Cooling: Central Air Heating: Electric Water Front: Yes Bay Front,Open Water,Gulf Front Bay/Gulf View,Open Water View

    Window Information

    Window Treatments: Impact Rstnce Window,Impact Rstnce Doors

  • Building Information

    Year Built: 2014 Total Units: 0.00 Floor Location: 139392 Construction: CBS,Combo Construction Security System: Electric Gate,On Premises System Roof: Metal Roof

  • Exterior Features

    Bar,Storage,Sprinkler System,Sandy Beach,Outdoor Shower,Outdoor Kitchen,Lighting,Detached Guest Qtrs,Gazebo,Fruit Tree(s),Fencing,Chickee Hut,Built-in Grill

    Pool Information

    In Ground,Concrete Heated: Yes Dimensions: 100 feet long

  • Guest House Information

    Legal

  • Lot Information

    Lot Dimensions: 252 ft wide Lot SqFt: 139,392 Lot SqFt Source: Tax Records 13 63 37 PLANTATION KEY PT GOVT LOT 1 AND ADJ BAY BTM G32-114 (see deed)

  • Property Information

    SQ ft (Living Area): 6,573 View: Bay/Gulf View,Open Water View Subdivision: Misc Plantation Key (85.0)

  • Listing Price Information

    List Price: $14,900,000

  • Tax Information

    Taxes: $92,231 Tax Year: 2025 Parcel Number: 00091852-000000 Tax Exemptions: None

  • Virtual Tour

    Virtual Tour (External Link)

  • Multi-Unit Information

    Pets Allowed: Pets Allowed

  • Homeowners Association Information

    Mandatory Home Owners Asc: No 1st Right of Refusal: No Association Fee: $0.00

  • Utility Information

    FKAA,Propane,Elect Separate Meter,Water Separate Meter,Whole House Generatr
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
102 Anglers Way, Islamorada, FL, 33036 $1,150,000 2 3 1,376 1,376 SqFt
88351 Old Highway HIGHWAY, Islamorada, FL, 33036 $15,990,000 6 9 7,590 7,590 SqFt
87895 Old Highway HIGHWAY, Islamorada, FL, 33036 $24,995,000 5 8 9,011 9,011 SqFt
88110 Overseas Highway, Islamorada, FL, 33036 $6,999,000 4 5 2,797 2,797 SqFt
87950 Overseas Highway .., Islamorada, FL, 33036 $3,800,000 5 3 2,464 2,464 SqFt
87445 Old Highway HIGHWAY, Islamorada, FL, 33036 $3,995,000 5 4 4,014 4,014 SqFt
87429 Old Highway HIGHWAY, Islamorada, FL, 33036 $18,999,000 6 8 6,692 6,692 SqFt
87429 Old Highway, Islamorada, FL, 33036 $18,999,000 6 6 6,054 6,054 SqFt
316 North Drive DRIVE, Islamorada, FL, 33036 $2,400,000 3 4 2,309 2,309 SqFt
316 N Dr, Islamorada, FL, 33036 $2,400,000 3 4 --

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ByOwner last updated this listing 07/25/2026 @ 14:33

MLS: 620077 LISTED BY: Brett Newman , Coldwell Banker Schmitt Islamorada 305-664-4470 SOURCE: Florida Keys MLS, Inc.

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