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For sale
    • $14,900,000

    139 Gimpy Gulch Dr, Plantation Key, FL 33036

    6beds
    6,573sqft
    : 
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    Single Family Residence
    Built in 2014
    3.2 Acres Lot
    $13,305,200 Zestimate®
    $2,267/sqft
    $-- HOA

    What's special

    New boat dockMultiple lounging areasPrivate gatesClassic island characterMature tropical landscaping
    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.
    47 days
    |
    4,210
    |
    289
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Brett Newman 305-393-1770,

    Coldwell Banker Schmitt Islamorada

    Source: FLKMLS,MLS#: 620077MLS LogoOriginating MLS: Florida Keys

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 6
      • Bathrooms: 9
      • Full bathrooms: 6
      • 1/2 bathrooms: 3
      Heating
      • Electric
      Cooling
      • Central Air
      Appliances
      • Included: More Appliances, Stainless Steel Appliance(s), Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer, Washer
      Features
      • Split Bedroom, Storage, Entrance Foyer, Pantry, Gym, Media Room
      • Flooring: Tile
      • Doors: Impact Rstnce Doors
      • Windows: Impact Rstnce Window
      • Furnished: Yes
      Interior area
      • Total interior livable area: 6,573 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 2
      • Parking features: Garage, Trailer Storage, Covered, Off Street, Guest, Open
      • Has garage: Yes
      • Has uncovered spaces: Yes
      Accessibility
      • Accessibility features: Yes
      Features
      • Patio & porch: Open Porch/Balcony, Patio
      • Exterior features: Bar, Storage, Sprinkler System, Sandy Beach, Outdoor Shower, Outdoor Kitchen, Lighting, Built-in Barbecue
      • Has private pool: Yes
      • Pool features: Heated, In Ground, Concrete
      • Fencing: Fenced
      • Has view: Yes
      • View description: Bay/Gulf View, Water
      • Has water view: Yes
      • Water view: Bay/Gulf View,Water
      • Waterfront features: Bay Front, Open Water, Gulf Front, Waterfront, Sandy Beach, Dock: Wood, Dock Length: 100, Dockage: Boat Ramp
      Lot
      • Size: 3.2 Acres
      • Dimensions: 252 ft wide
      • Features: 2 Less Than 5 Acres
      • Residential vegetation: Fruit Tree(s)
      Details
      • Additional structures: Guest House, Detached Guest Qtrs, Gazebo, Chickee Hut
      • Additional parcels included: 00091880000200
      • Parcel number: 00091852000000
      • Zoning: R1
      • Zoning description: Residential Single Family

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • CBS, Combo Construction
      • Roof: Metal
      Condition
      • Updated/Remodeled
      • New construction: No
      • Year built: 2014

      Utilities & green energy

      • Electric: Elect Separate Meter, Generator
      • Sewer: Public Sewer
      • Water: Water Separate Meter
      • Utilities for property: FKAA, Propane, Cable Connected

      Community & HOA

      Community
      • Features: Community Boat Ramp
      • Security: Security System, Electric Gate, On Premises System
      • Subdivision: Misc Plantation Key (85.0)
      HOA
      • Has HOA: No
      • Services included: None
      Location
      • Region: Plantation Key

      Financial & listing details

      • Price per square foot: $2,267/sqft
      • Tax assessed value: $10,873,196
      • Annual tax amount: $92,230
      • Date on market: 5/29/2026

        Estimated market value

        $13,305,200

        $12.51M - $14.10M

        $4,754/mo

        Price history

        DateEventPrice
        5/29/2026Listed for sale$14,900,000+86.3%$2,267/sqft
        Source: FLKMLS #620077 Report a problem
        9/1/2021Sold$8,000,000-5.8%$1,217/sqft
        Source: FLKMLS #582483 Report a problem
        1/13/2021Listing removed--
        Source: FLKMLS Report a problem
        6/30/2020Price change$8,490,000-4.6%$1,292/sqft
        Source: Coastal Realty of the Florida Keys #582483 Report a problem
        11/3/2019Price change$8,900,000-6.3%$1,354/sqft
        Source: Coastal Realty of the Florida Keys #582483 Report a problem
        10/27/2018Listed for sale$9,495,000+279.8%$1,445/sqft
        Source: Coastal Realty of the Florida Keys #582483 Report a problem
        10/7/2011Sold$2,500,000+25%$380/sqft
        Source: Public Record Report a problem
        6/18/2008Sold$2,000,000+245.4%$304/sqft
        Source: Public Record Report a problem
        2/12/1998Sold$579,000$88/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$92,231 +6.6%$9,723,830 +10%
        2024$86,535 +12.6%$8,839,845 +10%
        2023$76,871 +11.3%$8,036,223 +10%
        2022$69,064 +29%$7,305,657 +36.3%
        2021$53,550 -1%$5,358,238 -0.6%
        2020$54,074 $5,388,859 -2.5%
        2019$54,074 +1%$5,529,767 +4.7%
        2018$53,522 +8.1%$5,283,940 -0.7%
        2017$49,491 +7.5%$5,319,060 -7.5%
        2016$46,019 -3.4%$5,752,336 +15%
        2015$47,624 $5,001,746
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

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        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 33036

        Getting around

        23 / 100
        Car-Dependent
        48 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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