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For sale
  • $4,650,000

    1028 Flagler Ave, Key West, FL 33040

    4beds
    3,589sqft
    : 
    $29,327/mo
    Get pre-qualified
    Single Family Residence
    Built in 1958
    0.27 Acres Lot
    $4,280,400 Zestimate®
    $1,296/sqft
    $-- HOA

    What's special

    Custom swimming poolTropical mid-century modern architectureOutdoor kitchenGenerous proportionsHigh ceilingsMature palmsAbundant off-street parking
    A CASA MARINA ORIGINAL. Some houses capture a moment in time. Others seem to have understood, from the beginning, what makes Key West such an extraordinary place to live. Built in 1958, 1028 Flagler Avenue is a striking example of tropical mid-century modern architecture, set within a private three-building compound on 11,586 square feet in Casa Marina, one of the island's most distinguished neighborhoods. Behind substantial privacy walls lies a world of its own. Winding pathways lead through lush native and tropical gardens that seem borrowed from a movie, connecting the main residence, separate two-bedroom guest quarters, and detached garage/workshop. Mature palms, flowering gardens, shaded terraces, and a custom swimming pool create an extraordinary sense of seclusion. Inside, clean architectural lines, high ceilings, and generous proportions celebrate indoor-outdoor living. Expansive living and dining areas, a library, and a separate study offer room to gather or retreat. Impact-rated windows and doors provide modern peace of mind without sacrificing the home's character. The guest quarters include their own living area and kitchen, ideal for family and visitors. Together, the three buildings offer 3,589 square feet of combined enclosed space: 3,173 square feet of living area plus a 416-square-foot garage/workshop. Covered outdoor dining, an outdoor kitchen, and abundant off-street parking make this compound as practical as it is beautiful. Just two blocks from Higgs Beach and the Atlantic Ocean, with White Street Pier, waterfront parks, tennis, pickleball, and some of Key West's best-loved restaurants close at hand. Old Town is minutes away, yet the privacy and tranquility of Casa Marina remain entirely your own.
    23 days
    1,179
    97

    Zillow last checked:

    Listing updated:

    Listed by:

    Team Kaufelt 305-393-1267,

    Truman & Co. (KW)

    Source: FLKMLS,MLS#: 621710MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 5
      • Full bathrooms: 3
      • 1/2 bathrooms: 2
      Cooling
      • Central Air, Ceiling Fans(s)
      Appliances
      • Included: Washer, Dryer, Dishwasher, Refrigerator, Oven, Disposal, Freezer, Gas Appliances
      Features
      • Split Bedroom, Pantry
      • Flooring: Tile
      • Windows: Skylight(s)
      Interior area
      • Total structure area: 3,589
      • Total interior livable area: 3,589 sqft

      Property

      Parking
      • Parking features: Garage Door Opener
      • Has garage: Yes
      Features
      • Patio & porch: Open Porch/Balcony, Lanai
      • Exterior features: Fruit Tree(s), Lighting, Outdoor Shower
      • Has private pool: Yes
      • Pool features: In Ground
      • Fencing: Privacy
      Lot
      • Size: 0.27 Acres
      Details
      • Parcel number: 00058290000000
      • Zoning: SF - Single Family
      • Other equipment: Irrigation Equipment

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • CBS
      Condition
      • Updated/Remodeled
      • New construction: No
      • Year built: 1958

      Community & HOA

      Community
      • Features: Beach
      • Subdivision: Martello Towers (1.0)
      HOA
      • Has HOA: No
      • Services included: None
      Location
      • Region: Key West

      Financial & listing details

      • Price per square foot: $1,296/sqft
      • Tax assessed value: $3,062,256
      • Annual tax amount: $24,851
      • Date on market: 10/20/2026

        Estimated market value

        $4,280,400

        $4.07M - $4.49M

        Not available

        Price history

        DateEventPrice
        10/20/2026Listed for sale$4,650,000+184%$1,296/sqft
        Source: FLKMLS #621710 Report a problem
        10/15/2008Sold$1,637,500+187.3%$456/sqft
        Source: FLKMLS #107156 Report a problem
        3/6/1996Sold$570,000$159/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$24,852 +7.9%$2,784,826 +10%
        2024$23,028 +4.4%$2,531,660 +10%
        2023$22,067 +14.3%$2,301,509 +10%
        2022$19,302 +10.2%$2,092,281 +10%
        2021$17,512 +2.5%$1,902,074 +2.2%
        2020$17,092 $1,860,426 +1.2%
        2019$17,092 +0.3%$1,838,733 +0.9%
        2018$17,045 -1.1%$1,822,610 +3.4%
        2017$17,243 +1.5%$1,762,504 +9.2%
        2016$16,988 +3%$1,613,368 -6.1%
        2015$16,492 $1,718,743
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

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        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.
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        Climate risks

        Neighborhood: Casa Marina

        Getting around

        60 / 100
        Somewhat Walkable
        25 / 100
        Some Transit
        88 / 100
        Very Bikeable

        Nearby schools

        GreatSchools rating

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