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For sale
  • $1,100,000

    321 Tollgate Shores Dr, Islamorada, FL 33036

    2beds
    1,532sqft
    : 
    $6,448/mo
    Get pre-qualified
    Single Family Residence
    Built in 1993
    6,098 Square Feet Lot
    $1,039,600 Zestimate®
    $718/sqft
    $21/mo HOA

    What's special

    New dockAir conditioned garageFish cleaning stationMetal roofCovered parkingSpacious bonus roomDedicated tackle storage closet
    A unique opportunity to enjoy the Florida Keys boating lifestyle without the cost of waterfront ownership. This well-maintained dry lot home in desirable Tollgate Shores includes a deeded boat slip directly across the street, complete with a new dock, 20k boat lift, water, power, and a fish cleaning station. Enjoy the convenience of direct sight lines to your boat from the living room and front porch, with peekaboo views of Florida Bay and the iconic Channel 5 Bridge beyond. Upstairs, the home features two generously sized bedroom suites, each with its own ensuite bathroom. A pantry and laundry room are conveniently set off of the well-appointed, modern kitchen. The open-concept living area is highlighted by vaulted ceilings with exposed wood trusses and bamboo flooring. A clean interior offers a comfortable, move-in-ready space, with furnishings negotiable. The lower level includes covered parking, an air conditioned garage, a spacious bonus room, and a dedicated tackle storage closet, providing ample space for boating gear, hobbies, and everyday storage. A metal roof, high quality insulation and impact windows and doors add to the integrity and efficiency of this home. Located adjacent to the neighborhood park, the property benefits from additional open green space. The voluntary HOA is $250 annually. With quick boating access to both Florida Bay and the Atlantic Ocean via Channel 5, this property is well suited as a full-time residence, weekend retreat, or investment opportunity. Whether your priority is boating, fishing, or embracing the relaxed Florida Keys lifestyle, 321 Tollgate Shores offers a distinctive combination of convenience, functionality, and value with a niche setup.
    20 days
    |
    1,843
    |
    118
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Leslie Leopold 305-942-0215,

    Ocean Sotheby's International Realty,

    Annie Hagen 305-304-1762,

    Ocean Sotheby's International Realty

    Source: FLKMLS,MLS#: 620551MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 2
      • Bathrooms: 2
      • Full bathrooms: 2
      Heating
      • Has Heating (Unspecified Type)
      Cooling
      • Central Air, Ductless
      Appliances
      • Included: Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Disposal, Freezer, Wine Cooler, Stainless Steel Appliance(s)
      • Laundry: Laundry Room
      Features
      • Storage, Walk-in Closet(s)
      Interior area
      • Total structure area: 1,532
      • Total interior livable area: 1,532 sqft

      Property

      Parking
      • Parking features: Attached
      • Has attached garage: Yes
      Features
      • Patio & porch: Open Porch/Balcony
      • Exterior features: Outdoor Shower, Storage
      Lot
      • Size: 6,098 Square Feet
      • Dimensions: 60 X 100
      Details
      • Parcel number: 00390800000000
      • Zoning: R1 - Residential Single Family

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Other
      • Property subtype: Single Family Residence
      Materials
      • Frame, Combo Construction, Other
      Condition
      • Updated/Remodeled
      • New construction: No
      • Year built: 1993

      Community & HOA

      Community
      • Subdivision: Toll Gate Shores (73.5)
      HOA
      • Has HOA: No
      • Services included: Common Area Mnt, Other
      • HOA fee: $250 annually
      Location
      • Region: Islamorada

      Financial & listing details

      • Price per square foot: $718/sqft
      • Tax assessed value: $784,290
      • Annual tax amount: $8,049
      • Date on market: 7/7/2026
      • Listing terms: Cash,Conventional

        Estimated market value

        $1,039,600

        $988,000 - $1.09M

        $4,772/mo

        Price history

        DateEventPrice
        7/7/2026Listed for sale$1,100,000+46.7%$718/sqft
        Source: Key West AOR #620551 Report a problem
        10/8/2020Sold$750,000-4.9%$490/sqft
        Source: FLKMLS #591151 Report a problem
        6/7/2020Listed for sale$789,000+64.7%$515/sqft
        Source: Century 21 Island Life (ISL) #591151 Report a problem
        5/28/2004Sold$479,000$313/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$8,050 +5.1%$784,290 +7.1%
        2024$7,660 +4.6%$732,027 +10%
        2023$7,324 +8.8%$665,479 +10%
        2022$6,732 +7%$604,981 +10%
        2021$6,291 +161.7%$549,983 +121%
        2020$2,404 $248,893 +2.3%
        2019$2,404 +0.5%$243,298 +1.9%
        2018$2,392 -17.8%$238,762 +2.1%
        2017$2,909 +3.7%$233,852 +2.1%
        2016$2,806 -2.2%$229,043 +0.7%
        2015$2,871 $227,451
        Find assessor info on the county website

        Monthly payment

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        Payment breakdown

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        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

        17 / 100
        Car-Dependent
        50 / 100
        Bikeable

        Nearby schools

        GreatSchools rating

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