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For sale
  • $6,850,000

    103 Front St, Key West, FL 33040

    3beds
    3,000sqft
    : 
    $45,519/mo
    Get pre-qualified
    Single Family Residence
    Built in 1918
    8,712 Square Feet Lot
    $-- Zestimate®
    $2,283/sqft
    $3,405/mo HOA

    What's special

    Adorned by tropical foliageDramatic staircaseCustom beams and woodworkImposing structureCustom features throughout
    103 Front Street is a one of a kind masterpiece of architectural design and modern aesthetic. Built in the early 1900s, this imposing structure has been thouroughly restored and updated into a stunning home. The interior features a large great room with soaring ceilings, custom beams and woodwork. This home is perfect for entertaining on a large scale or enjoying a quiet evening. A dramatic staircase leads to a second floor walkway which is open to the main level. The floor plan provides privacy for each bedroom with the primary suite at one end of the hallway and a guest bedroom suite at the other end. Another guest bedroom and bath are on the first floor creating an option for a first floor primary bedroom. Custom features throughout are evidence of the artistic ingenuity used in the design of this impressive home. The kitchen features custom wood cabinets and granite countertops and is open to the dining area. Tall windows and french doors flood the home with sunlight. This home is perfect for indoor/outdoor entertaining. A wet bar features custom built ins plus an icemaker and refrigerator. Fronted by a white picket fence, the home sits back from the street and is adorned by tropical foliage. This unique structure with thick brick walls and impressivly tall windows offers passers by a glimpse of the historic origins of the Truman Annex. Its location in the heart of old town Key West provides easy walkability to the waterfront promenade, Ft. Taylor beach, cultural venues, shops and restaurants. The property comprises two lots with a large swimming pool and spa plus an outdoor shower between the covered and open air loggia and parking. There's plenty of space for entertaining outdoors under the palm trees. This estate home is one of a kind was restored to the highest standards. One must see this home to appreciate the incredible design and attention to detail that went into this historic treasure.
    277 days
    |
    2,034
    |
    90
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Laura A McChesney 305-923-6639,

    Preferred Properties (KW),

    Key West Sisters 305-747-0369,

    Preferred Properties (KW)

    Source: FLKMLS,MLS#: 617136MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 3
      • Full bathrooms: 3
      Cooling
      • Central Air, Ceiling Fans(s)
      Appliances
      • Included: Washer, Dryer, Dishwasher, Refrigerator, Oven, Microwave, Ice Maker
      Features
      • Built-in Features, Granite Counters
      • Flooring: Wood, Marble
      Interior area
      • Total structure area: 3,000
      • Total interior livable area: 3,000 sqft

      Property

      Features
      • Patio & porch: Patio
      • Exterior features: Lighting, Outdoor Shower, Storage, Water Display
      • Has private pool: Yes
      • Pool features: In Ground, Concrete
      • Fencing: Fenced
      Lot
      • Size: 8,712 Square Feet
      Details
      • Parcel number: 00004590002157
      • Zoning: HPRD - Hist Planned Redevelopment & Dev Dist
      • Other equipment: Irrigation Equipment

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Combo Construction, Other
      Condition
      • Year built: 1918

      Community & HOA

      Community
      • Security: Security Guard, Other, Security System
      • Subdivision: The Foundry (1.0)
      HOA
      • Has HOA: Yes
      • Services included: Maintenance Structure, Insurance, Common Area Mnt, Security
      • HOA fee: $10,214 quarterly
      Location
      • Region: Key West

      Financial & listing details

      • Price per square foot: $2,283/sqft
      • Tax assessed value: $4,273,714
      • Annual tax amount: $34,272
      • Date on market: 11/1/2025

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        11/1/2025Listed for sale$6,850,000+5.4%$2,283/sqft
        Source: FLKMLS #617136 Report a problem
        4/1/2025Listing removed$6,500,000$2,167/sqft
        Source: Engel & Volkers #NS1080891 Report a problem
        9/12/2024Listed for sale$6,500,000$2,167/sqft
        Source: Stellar MLS #NS1080891 Report a problem
        9/6/2024Listing removed$6,500,000$2,167/sqft
        Source: Key West AOR #609252 Report a problem
        3/18/2024Listed for sale$6,500,000+3.2%$2,167/sqft
        Source: FLKMLS #609252 Report a problem
        5/21/2022Listing removed--
        Source: FLKMLS #598752 Report a problem
        12/8/2021Listed for sale$6,300,000+5.9%$2,100/sqft
        Source: FLKMLS #598752 Report a problem
        6/1/2018Listing removed$5,950,000$1,983/sqft
        Source: Keller Williams Key West Compass Realty #577304 Report a problem
        11/3/2017Listed for sale$5,950,000$1,983/sqft
        Source: Keller Williams Key West Compass Realty #577304 Report a problem
        6/1/2017Listing removed$5,950,000$1,983/sqft
        Source: Compass Realty (KW) #572689 Report a problem
        11/10/2016Listed for sale$5,950,000+1703%$1,983/sqft
        Source: Compass Realty (KW) #572689 Report a problem
        4/28/1997Sold$330,000$110/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$35,716 +4.2%$4,273,714 +4.2%
        2024$34,273 +5.1%$4,099,838 +10%
        2023$32,620 +14.8%$3,727,125 +10%
        2022$28,409 -0.3%$3,388,295 +5.7%
        2021$28,504 -5.7%$3,206,196 -6.1%
        2020$30,236 $3,413,546 -0.2%
        2019$30,236 -1%$3,418,720 +1.8%
        2018$30,554 -0.4%$3,357,602 +0.6%
        2017$30,663 +0.6%$3,336,822 +10.9%
        2016$30,467 +4.1%$3,009,375 +12.3%
        2015$29,267 $2,679,948
        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.
        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: Truman Annex

        Getting around

        79 / 100
        Very Walkable
        28 / 100
        Some Transit
        79 / 100
        Very Bikeable

        Nearby schools

        GreatSchools rating

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