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Sold for $4,200,000
  • $4,200,000

    166 Bayview Dr, Islamorada, FL 33036

    4beds
    2,478sqft
    Single Family Residence
    Built in 1968
    0.26 Acres Lot
    $4,197,600 Zestimate®
    $1,695/sqft
    $7,754 Estimated rent

    Home value

    $4,197,600

    $3.99M - $4.45M

    $7,754/mo

    Zestimate® history
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    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.

    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

    Bought with:

    Drew Moret, 3463076

    Palm House Real Estate

    Source: FLKMLS,MLS#: 617501MLS Logo

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 4
    • Bathrooms: 4
    • Full bathrooms: 4
    Cooling
    • Central Air
    Appliances
    • Included: Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave
    Features
    • Flooring: Tile, Terrazzo, Marble
    • Furnished: Yes
    Interior area
    • Total structure area: 2,478
    • Total interior livable area: 2,478 sqft

    Property

    Features
    • Patio & porch: Open Porch/Balcony
    • Exterior features: Chickee Hut, Outdoor Shower
    • Has private pool: Yes
    • Pool features: In Ground, Concrete
    • Fencing: Fenced,Privacy
    • On waterfront: Yes
    Lot
    • Size: 0.26 Acres
    Details
    • Parcel number: 00391950000000
    • Zoning: R1 - 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

    Community & HOA

    Community
    • Features: Bike Paths
    • Subdivision: Safety Harbor (74.0)
    HOA
    • Has HOA: No
    • Services included: None
    • HOA fee: $250 annually
    Location
    • Region: Islamorada

    Financial & listing details

    • Price per square foot: $1,695/sqft
    • Tax assessed value: $2,930,729
    • Annual tax amount: $22,353
    • Date on market: 11/29/2025
    • Listing terms: Cash,Conventional

    Price history

    DateEventPrice
    9/2/2026Sold$4,200,000-10.6%$1,695/sqft
    Source: FLKMLS #617501 Report a problem
    7/16/2026Pending sale$4,700,000$1,897/sqft
    Source: FLKMLS #617501 Report a problem
    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
    11/18/2004Sold$2,225,000+168.4%$898/sqft
    Source: Public Record 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

    Neighborhood: 33036

    Nearby schools

    GreatSchools rating
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    Estimated market value
    $4,197,600
    Get a cash offer in 3 minutes
    Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
    Estimated market value
    $4,197,600