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For sale
    • Price cut: $900K (5/18)
    $4,700,000

    166 Bayview Dr, Islamorada, FL 33036

    4beds
    2,478sqft
    : 
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    Single Family Residence
    Built in 1968
    0.26 Acres Lot
    $4,350,800 Zestimate®
    $1,897/sqft
    $21/mo HOA

    What's special

    Unobstructed water viewsDeep-water dockage with davitsWell-appointed kitchenBrick paver walkways
    Welcome to 166 Bayview Drive, a rare bayfront estate in the prestigious Safety Harbor neighborhood of Lower Matecumbe Key. Located at Mile Marker 74, this property offers direct access to Florida Bay and the Atlantic Ocean, placing you in the heart of Islamorada's world-class boating and sportfishing scene.The home enjoys unobstructed water views and nightly sunsets that paint the sky in brilliant hues. A Tiki at the water's edge provides a perfect perch for morning coffee or evening cocktails, while mature landscaping adds privacy and tropical charm.Boaters will appreciate the deep-water dockage with davits, ideal for quick access to open water. The 2,478-square-foot residence features 4 bedrooms and 4 bathrooms, with tile flooring throughout and expansive windows that frame the bay. The open-concept living and dining areas flow into a well-appointed kitchen. The primary suite offers direct water views and private outdoor access.Outdoor living is elevated with a spacious pool and deck area, balcony, and brick paver walkways. The white picket fencing and lush landscaping complete the coastal aesthetic.Additional features include CBS construction, off-street parking, FKAA water service, septic system, and low HOA fees. Pets are welcome.Whether you're seeking a full-time residence, seasonal retreat, or investment opportunity, 166 Bayview Drive delivers unmatched location, views, and lifestyle in the Florida Keys.
    224 days
    |
    530
    |
    22
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Judy Rossignol 305-393-0523,

    Paradise Florida Keys Real Estate, a Luxury Brand,

    Richard Trottnow 305-842-1151,

    Paradise Florida Keys Real Estate, a Luxury Brand

    Source: FLKMLS,MLS#: 617501MLS LogoOriginating MLS: Florida Keys

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      • Full bathrooms: 4
      Cooling
      • Central Air
      Appliances
      • Included: Washer, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
      Features
      • Flooring: Tile, Marble, Terrazzo
      • Doors: Sliding Glass Doors, Impact Rstnce Doors
      • Windows: Impact Rstnce Window, Clam Shell
      • Furnished: Yes
      Interior area
      • Total interior livable area: 2,478 sqft
      Video & virtual tour

      Property

      Parking
      • Parking features: Off Street
      Accessibility
      • Accessibility features: No
      Features
      • Levels: Two
      • Stories: 2
      • Patio & porch: Open Porch/Balcony
      • Exterior features: Outdoor Shower
      • Has private pool: Yes
      • Pool features: In Ground, Concrete
      • Fencing: Privacy,Fenced
      • Has view: Yes
      • View description: Bay/Gulf View, Water
      • Has water view: Yes
      • Water view: Bay/Gulf View,Water
      • Waterfront features: Bay Front, Waterfront, Dock Length: 40, Dockage: Davits
      Lot
      • Size: 0.26 Acres
      • Features: Less Than 1/4 Acre
      Details
      • Additional structures: Chickee Hut
      • Parcel number: 00391950000000
      • Zoning: R1
      • Zoning description: Residential Single Family

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • CBS
      Condition
      • Updated/Remodeled
      • New construction: No
      • Year built: 1968

      Utilities & green energy

      • Sewer: Municipal Sewer, Public Sewer
      • Utilities for property: FKAA, Buyer to Verify, Cable Connected

      Community & HOA

      Community
      • Features: Bike Paths
      • Subdivision: Safety Harbor (74.0)
      HOA
      • Has HOA: Yes
      • Services included: None
      • HOA fee: $250 yearly
      Location
      • Region: Islamorada

      Financial & listing details

      • Price per square foot: $1,897/sqft
      • Tax assessed value: $2,930,729
      • Annual tax amount: $22,353
      • Date on market: 11/29/2025
      • Listing terms: Cash,Conventional

        Estimated market value

        $4,350,800

        $4.13M - $4.57M

        $6,716/mo

        Price history

        DateEventPrice
        5/18/2026Price change$4,700,000-16.1%$1,897/sqft
        Source: Key West AOR #617501 Report a problem
        11/29/2025Listed for sale$5,600,000+348.4%$2,260/sqft
        Source: FLKMLS #617501 Report a problem
        10/26/2013Listing removed$1,249,000$504/sqft
        Source: Key Largo Realty, Inc. #556306 Report a problem
        7/22/2013Price change$1,249,000-37.4%$504/sqft
        Source: RE/MAX Keys Properties #556306 Report a problem
        12/2/2012Price change$1,995,000-16.8%$805/sqft
        Source: Key Largo Realty, Inc. #556306 Report a problem
        11/9/2011Listed for sale$2,399,000-4%$968/sqft
        Source: Key Largo Realty, Inc. #556306 Report a problem
        4/16/2011Listing removed$2,499,000$1,008/sqft
        Source: RE/MAX Keys to the Key Report a problem
        6/11/2010Price change$2,499,000-19.4%$1,008/sqft
        Source: RE/MAX Keys to the Key Report a problem
        12/12/2009Listed for sale$3,100,000+39.3%$1,251/sqft
        Source: RE/MAX Keys to the Key Report a problem
        11/5/2004Sold$2,225,000+168.4%$898/sqft
        Source: FLKMLS #521781 Report a problem
        5/16/1997Sold$829,000+75263.6%$335/sqft
        Source: Public Record Report a problem
        1/24/1995Sold$1,100
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$23,887 +6.9%$2,376,692 +10%
        2024$22,353 +4.4%$2,160,629 +10%
        2023$21,417 +18.8%$1,964,208 +10%
        2022$18,023 +8.5%$1,785,644 +10%
        2021$16,617 -2.1%$1,623,313 +2.4%
        2020$16,980 $1,584,862 -7%
        2019$16,980 +5.6%$1,703,429 +6.7%
        2018$16,086 +8.6%$1,596,730 +9.9%
        2017$14,805 +11.4%$1,452,653 +3.4%
        2016$13,294 +1.1%$1,404,450 +19.7%
        2015$13,145 $1,172,869
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        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

        7 / 100
        Car-Dependent
        42 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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