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$14,900,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 6 Beds
  • 7 Full Baths
  • 3 Partial Baths
  • 6,573 Sq. Ft.
  • Updated 1 day ago
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139 Gimpy Gulch Drive, Plantation Key, FLVideo Tour of 139 Gimpy Gulch Drive, Plantation Key, FL.
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. The resort-style pool and 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 a main home with ground level living, a tri-level guest home, and a large garage/media house all with classic island character. Both residences offer chef kitchens with high-end appliances including SubZero and La Cornue. For boaters, a new dock offers immediate access to the bay and ocean and the included neighboring lot provides convenient boat ramp access. This one-of-kind package also includes a 34' Edgewater with twin 400 hp Yahamas (in indoor storage), a pair of Waverunners and UTV tow vehicle, plus fishing rods, kayaks, paddle boards, and bicycles to enjoy everything Islamorada has to offer. Not only is this estate ready for fun, it's also ready to enjoy with furniture, furnishings, 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.

Full Property Details for 139 Gimpy Gulch Dr

General

  • Price: $14,900,000
  • Taxes: $92,230 (2025)
  • Status: Active
  • Type: Single Family
  • Source: 927
  • MLS ID: 620077
  • Updated: 5/29/2026
  • Added to Site: 1 day(s) ago

Interior

  • Interior Features: Entrance Foyer, Pantry, Security System, Split Bedroom, Storage, Gym, Media Room
  • Appliances: Stainless Steel Appliance(s), Dishwasher, Dryer, Microwave, More Appliances, Oven, Range, Refrigerator, Washer
  • Flooring: Tile

Rooms

Bathrooms

  • Total Bathrooms: 10
  • Full Bathrooms: 7
  • Half Bathrooms: 3

Bedrooms

  • Total Bedrooms: 6

Additional Information

  • Shared Amenities: Community Boat Ramp
  • Pool: Yes
  • Pool Description: Concrete, Heated, In Ground
  • Security/Safety: Electric Gate, On Premises System

Exterior

  • Exterior Features: Lighting, Bar, Built-in Grill, Chickee Hut, Detached Guest Qtrs, Fencing, Fruit Tree(s), Gazebo, Outdoor Kitchen, Outdoor Shower, Sandy Beach, Sprinkler System, Storage
  • Deck/Patio: Open Porch/Balcony, Patio
  • Porch/Patio/Deck: Open Porch/Balcony, Patio

Parking

  • Garage: Yes
  • Parking Features: Open

Location

  • Area: 25 - Plantation Key
  • County: Monroe
  • Subdivision: Misc Plantation Key (85.0)
  • Driving Directions: Gated - no access without making an appointment with the listing agent. Plantation Key bayside mm 87. Driveway is between Rain Barrel and Founder's Park.

Community

  • Assoc. Fees Include: None
  • Pets Allowed: Yes

Heating & Cooling

  • Central air: Yes
  • Air Conditioning: Yes
  • Cooling Type: Central Air
  • Heating Type: Electric

Structural Information

  • Architectural Style: Above Flood
  • Construction Status: Updated/Remodeled
  • Construction: CBS, Combo Construction
  • Roof: Metal
  • Windows/Doors: Impact Rstnce Doors, Impact Rstnce Window
  • Square Feet: 6,573
  • Sq. Ft. Source: Tax Records
  • Year Built: 2014
  • Property Condition: Updated/Remodeled

Lot Features

  • Property View: Open Water View, Bay
  • Lot Size (Acres): 3.2
  • Lot Size (Sq. Ft.): 139,392
  • Lot Size Source: Tax Records
  • Lot Dimensions: 252 ft wide
  • Zoning: R1 - Residential Single Family

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Bay Front, Gulf Front, Open Water

Financial Considerations

  • Tax Amount: $92,230.77
  • Tax Year: 2025

Disclosures and Reports

  • Legal Description: 13 63 37 PLANTATION KEY PT GOVT LOT 1 AND ADJ BAY BTM G32-114 (see deed)
  • Flood Zone: VE, AE, 0.2 PCT ANN
  • APN: 00091852-000000

Listed by Coldwell Banker Schmitt Islamorada, Brett Newman (305) 393-1770

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Listing agent

— 139 Gimpy Gulch Dr —

  • Brett Newman

    Coldwell Banker Schmitt Islamorada

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 139 Gimpy Gulch Dr

School District:Monroe County School District, Middle Torch Key, FL
NameGradesDistance
Plantation Key School
100 Lake Road, Tavernier, FL 33070
PK-82.7 mi
Coral Shores High School
89901 Old Highway, Tavernier, FL 33070
9-123.1 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 139 Gimpy Gulch Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/29/2026
Listed
$14,900,000
86.25%
MLS
9/01/2021
Sold
$8,000,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 139 Gimpy Gulch Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
100%
$10,873,196
-1%
2024
-100%
$10,950,676
26%
2023
$76,871
44%
$8,672,783
62%
2021
$53,550
-22%
$5,358,238
-27%
2022
$69,064
29%
$7,305,657
36%
2021
$53,550
—
$5,388,859
6%
2019
$53,522
8%
$5,068,236
10%
2018
$49,491
8%
$4,607,488
-13%
2017
$46,019
-3%
$5,319,060
-8%
2016
$47,624
13%
$5,752,336
66%
2015
$42,080
53%
$3,461,674
37%
2014
$27,508
3%
$2,527,825
5%
2013
$26,630
—
$2,416,635
—
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Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 139 Gimpy Gulch Dr

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by Coldwell Banker Schmitt Islamorada, Brett Newman (305) 393-1770

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139 Gimpy Gulch Drive, Plantation Key, FL 33036 (MLS# 620077) is a Single Family property with 6 bedrooms, 7 full bathrooms and 3 partial bathrooms. 139 Gimpy Gulch Drive is currently listed for $14,900,000 and was received on May 29, 2026. Want to learn more about 139 Gimpy Gulch Drive? Do you have questions about finding other Single Family real estate for sale in Plantation Key? You can browse all Plantation Key real estate or contact a Coldwell Banker agent to request more information.

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