About 139 Gimpy Gulch Drive
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 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 retreat.
Features of 139 Gimpy Gulch Drive
| MLS® # | 620077 |
|---|---|
| Price | $14,900,000 |
| Bedrooms | 6 |
| Bathrooms | 9.00 |
| Full Baths | 6 |
| Half Baths | 3 |
| Square Footage | 6,573 |
| Acres | 3.20 |
| Year Built | 2014 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Status | Active |
Community Information
| Address | 139 Gimpy Gulch Drive |
|---|---|
| Area | 25 - Plantation Key |
| Subdivision | Misc Plantation Key (85.0) |
| City | Plantation Key |
| County | Monroe |
| State | FL |
| Zip Code | 33036 |
Amenities
| Amenities | Community Boat Ramp |
|---|---|
| Utilities | FKAA, Propane, Whole House Generatr, Water Separate Meter, Elect Separate Meter |
| Parking Spaces | 2 |
| Parking | Garage, Open Parking, Guest Parking, Off Street Parking, Trailer Storage, Covered Parking |
| View | Bay/Gulf View, Open Water View |
| Is Waterfront | Yes |
| Waterfront | Bay Front, Gulf Front, Open Water |
| Has Pool | Yes |
| Pool | In Ground, Concrete |
Interior
| Interior Features | Split Bedroom, Pantry, Entrance Foyer, Security System, Storage |
|---|---|
| Appliances | More Appliances, Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Stainless Steel Appliance(s) |
| Heating | Electric |
| Cooling | Central Air |
| Fireplace | No |
| Has Basement | No |
Exterior
| Exterior Features | Bar, Built-in Grill, Chickee Hut, Fencing, Fruit Tree(s), Gazebo, Detached Guest Qtrs, Lighting, Outdoor Kitchen, Outdoor Shower, Sandy Beach, Sprinkler System, Storage |
|---|---|
| Lot Description | 2 Less Than 5 Acres |
| Windows | Impact Rstnce Window, Impact Rstnce Doors |
| Roof | Metal Roof |
| Construction | CBS, Combo Construction |
Additional Information
| Date Listed | May 29th, 2026 |
|---|---|
| Days on Market | 33 |
| Zoning | R1 - Residential Single Family |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Agent | Brett Newman |
|---|---|
| Office | Coldwell Banker Schmitt Islamorada |