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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
    $2,447,000 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.
    109 days
    |
    1,103
    |
    15
    |

    Zillow last checked: 8 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

    $2,447,000

    $2.32M - $2.57M

    $7,402/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
    $14,564/mo
    Principal & interest
    $12787
    Property taxes
    $1777

      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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