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For sale
  • Price cut: $100K (1/27)
    $2,600,000

    16 Azalea Dr, Key West, FL 33040

    4beds
    2,321sqft
    : 
    Single Family Residence
    Built in 1965
    6,098.4 Square Feet Lot
    $2,452,300 Zestimate®
    $1,120/sqft
    $-- HOA

    What's special

    Shaker-style cabinetryTropical palmsMaximize lightV-crimp metal roofWood privacy fenceQuartz countertopsDecorative shell features
    Welcome to 16 Azalea Drive, a completely reimagined home that embodies sophisticated coastal living, blending modern elegance with meticulous attention to detail at every turn. Thoughtfully redesigned from the ground up, this 4-bedroom, 3-bath property spans nearly 2,400 sq ft of refined living space. The open layout creates a seamless flow between the living, dining & kitchen areas, each curated to maximize light, function & aesthetic appeal. Impact-rated windows & sliding glass doors frame lush tropical views & invite in the natural beauty of the Florida Keys, while the soft coastal palette & high-end finishes create a serene, contemporary atmosphere. The custom kitchen is both striking & functional, featuring quartz countertops, shaker-style cabinetry, a farmhouse sink & top-of-the-line stainless steel appliances. Bathrooms are masterfully finished with designer vanities, custom glass shower enclosures & LED-lit mirrors, creating a spa-like retreat. Throughout the interior, new tile flooring laid in a herringbone pattern adds visual interest & luxury underfoot, complemented by modern black fixtures & ceiling fans that bring a clean architectural touch. This property underwent a comprehensive renovation, including full replacement of plumbing & electrical components, a seamless V-Crimp metal roof, exterior stucco, & interior/exterior painting. The landscape was redesigned with artificial turf, tropical palms & decorative shell features, creating a refined, low-maintenance aesthetic. Expansive deck & patio areas are ideal for outdoor living, with paver walkways leading to a pool & hot tub beside a private canal-front setting. Situated on a wide canal with excellent boating access, this residence offers the ultimate Keys lifestyle for those who appreciate fine craftsmanship, privacy & quick access to open water. A new wood privacy fence, polished detailing & smart LED lighting complete this exceptional home where craftsmanship, comfort & design excellence converge.
    136 days
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    841
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    23
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    Zillow last checked: 7 hours ago

    Listing updated: February 14, 2026 at 10:55pm

    Listed by:

    Tommy Mack 305-731-7910,

    Coastal Collection Real Estate Inc.,

    Jenny Benson 775-835-9668,

    Coastal Collection Real Estate Inc.

    Source: FLKMLS,MLS#: 617283MLS LogoOriginating MLS: Key West Association

    Tour with a local agent

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 3
      • Full bathrooms: 3
      Heating
      • Central
      Cooling
      • Central Air, Ceiling Fans(s)
      Appliances
      • Included: Washer, Stainless Steel Appliance(s), Disposal, Microwave, Refrigerator, Dishwasher, Dryer
      Features
      • Cathedral Ceiling(s), Walk-In Closet(s), Utility Room
      • Flooring: Tile
      • Doors: Impact Rstnce Doors
      • Windows: Impact Rstnce Window
      Interior area
      • Total interior livable area: 2,321 sqft

      Property

      Parking
      • Parking features: Off Street
      Features
      • Levels: Multi/Split
      • Patio & porch: Open Porch/Balcony, Deck
      • Has private pool: Yes
      • Pool features: In Ground, Concrete
      • Has view: Yes
      • View description: Canal
      • Has water view: Yes
      • Water view: Canal
      • Waterfront features: Canal Front, Waterfront, Dock: Concrete
      Lot
      • Size: 6,098.4 Square Feet
      • Features: Less Than 1/4 Acre
      Details
      • Parcel number: 00133950000000
      • Zoning: IS
      • Zoning description: Improved Subivision District

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Combo Construction
      • Roof: Metal
      Condition
      • Updated/Remodeled
      • New construction: No
      • Year built: 1965

      Utilities & green energy

      • Sewer: Municipal Sewer, Public Sewer
      • Utilities for property: FKAA

      Community & HOA

      Community
      • Subdivision: Key Haven 1st Add (5.0)
      HOA
      • Has HOA: No
      • Services included: None
      Location
      • Region: Key West

      Financial & listing details

      • Price per square foot: $1,120/sqft
      • Tax assessed value: $1,350,068
      • Annual tax amount: $9,387
      • Date on market: 11/11/2025
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        Estimated market value

        $2,452,300

        $2.33M - $2.57M

        $7,962/mo

        Price history

        Price history
        DateEventPrice
        1/27/2026Price change$2,600,000-3.7%$1,120/sqft
        Source: Key West AOR #617283 Report a problem
        12/8/2025Price change$2,700,000-5.2%$1,163/sqft
        Source: Key West AOR #617283 Report a problem
        11/11/2025Listed for sale$2,849,000+111%$1,227/sqft
        Source: Key West AOR #617283 Report a problem
        10/28/2024Sold$1,350,000-6.9%$582/sqft
        Source: Key West AOR #609545 Report a problem
        10/25/2024Pending sale$1,450,000$625/sqft
        Source: FLKMLS #609545 Report a problem
        9/26/2024Contingent$1,450,000$625/sqft
        Source: FLKMLS #609545 Report a problem
        9/5/2024Listed for sale$1,450,000$625/sqft
        Source: FLKMLS #609545 Report a problem
        6/10/2024Contingent$1,450,000$625/sqft
        Source: FLKMLS #609545 Report a problem
        4/11/2024Listed for sale$1,450,000-8.7%$625/sqft
        Source: FLKMLS #609545 Report a problem
        4/11/2024Listing removed--
        Source: Key West AOR #604897 Report a problem
        5/24/2023Price change$1,589,000-5.9%$685/sqft
        Source: FLKMLS #604897 Report a problem
        4/11/2023Listed for sale$1,689,000-3.5%$728/sqft
        Source: FLKMLS #604897 Report a problem
        7/20/2022Listing removed--
        Source: FLKMLS #601827 Report a problem
        7/16/2022Listed for sale$1,750,000+264.6%$754/sqft
        Source: FLKMLS #601827 Report a problem
        9/28/2011Sold$480,000-46.7%$207/sqft
        Source: FLKMLS #113795 Report a problem
        6/19/2007Sold$900,000+125%$388/sqft
        Source: Public Record Report a problem
        10/11/2001Sold$400,000+66.7%$172/sqft
        Source: Public Record Report a problem
        11/1/1994Sold$240,000$103/sqft
        Source: Public Record Report a problem

        Public tax history

        Public tax history
        YearProperty taxesTax assessment
        2025$12,244 +30.4%$1,350,068 +44.1%
        2024$9,387 +20.9%$937,212 +10%
        2023$7,767 +5.7%$852,011 +10%
        2022$7,351 +7.5%$774,555 +10%
        2021$6,835 +3.7%$704,141 +4.9%
        2020$6,594 $671,173 +2.1%
        2019$6,594 +1.6%$657,168 +1.2%
        2018$6,488 -1.5%$649,311 +2.7%
        2017$6,588 +3.4%$632,310 +5.3%
        2016$6,370 +2%$600,611 +3.1%
        2015$6,244 $582,698

        Find assessor info on the county website

        BuyAbility℠ payment

        Est. payment
        $15,030/mo
        Principal & interest
        $13253
        Property taxes
        $1777
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          Climate risks

          Neighborhood: 33040

          Getting around

          8 / 100
          Car-Dependent
          21 / 100
          Minimal Transit
          67 / 100
          Bikeable

          Nearby schools

          GreatSchools rating

          Local experts in 33040

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