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For sale
  • $6,850,000

    103 Front St, Key West, FL 33040

    3beds
    4,200sqft
    : 
    Single Family Residence
    Built in 1918
    8,712 Square Feet Lot
    $-- Zestimate®
    $1,631/sqft
    $3,405/mo HOA

    What's special

    Large swimming poolPrivate patioTropical foliageGranite countertopsExtra tall windowsFrench doorsWhite picket fence
    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. A dramatic staircase leads to a second floor walkway which is open to the main level. On one end is the primary bedroom with a large en suite. At the other end is an en suite guest bedroom. The custom features throughout are evidence of the ingenuity used in the design of this impressive home. A third bedroom and full bath on the main floor features doors that open to a separate private patio. The kitchen features custom wood cabinets and granite countertops and is open to the dining area. Extra tall windows and french doors flood the home with sunlight. Entertaining indoors or out is easy in this spacious home. 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 is set on two lots with a large swimming pool and spa between the covered open air loggia and parking. There's a poolside outdoor shower and lots of space for entertaining on a grand or intimate scale. 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.
    140 days
    |
    2,773
    |
    61
    |

    Zillow last checked: 7 hours ago

    Listing updated: March 20, 2026 at 01:55am

    Listed by:

    Laura A McChesney 305-923-6639,

    Preferred Properties (KW),

    Key West Sisters 305-747-0369,

    Preferred Properties (KW)

    Source: FLKMLS,MLS#: 617136MLS LogoOriginating MLS: Key West Association

    Tour with a local agent

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 3
      • Full bathrooms: 3
      Cooling
      • Central Air, Ceiling Fans(s)
      Appliances
      • Included: Washer, Ice Machine, Microwave, Oven, Refrigerator, Dishwasher, Dryer
      Features
      • Wet Bar, Built-in Cabinets, Granite Counters, Cathedral Ceiling(s)
      • Flooring: Wood, Marble
      • Doors: Impact Rstnce Doors, French Doors
      • Windows: Double Hung Windows, Wood Frames, Other
      Interior area
      • Total interior livable area: 4,200 sqft

      Property

      Parking
      • Total spaces: 2
      • Parking features: Carport, Off Street
      • Has carport: Yes
      Features
      • Levels: Two
      • Stories: 2
      • Patio & porch: Patio
      • Exterior features: Water Display, Storage, Sprinkler System, Outdoor Shower, Lighting
      • Has private pool: Yes
      • Pool features: In Ground, Concrete
      • Fencing: Fenced
      • Water view: None
      • Waterfront features: None, Dockage: None
      Lot
      • Size: 8,712 Square Feet
      • Features: Less Than 1/4 Acre
      Details
      • Parcel number: 00004590002157
      • Zoning: HPRD
      • Zoning description: Hist Planned Redevelopment & Dev Dist

      Construction

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

      Utilities & green energy

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

      Community & HOA

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

      Financial & listing details

      • Price per square foot: $1,631/sqft
      • Tax assessed value: $4,273,714
      • Annual tax amount: $34,272
      • Date on market: 11/1/2025
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        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        Price history
        DateEventPrice
        11/1/2025Listed for sale$6,850,000+5.4%$1,631/sqft
        Source: FLKMLS #617136 Report a problem
        4/1/2025Listing removed$6,500,000$1,548/sqft
        Source: Engel & Volkers #NS1080891 Report a problem
        9/12/2024Listed for sale$6,500,000$1,548/sqft
        Source: Stellar MLS #NS1080891 Report a problem
        9/6/2024Listing removed$6,500,000$1,548/sqft
        Source: Key West AOR #609252 Report a problem
        3/18/2024Listed for sale$6,500,000+3.2%$1,548/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%$1,500/sqft
        Source: FLKMLS #598752 Report a problem
        6/1/2018Listing removed$5,950,000$1,417/sqft
        Source: Keller Williams Key West Compass Realty #577304 Report a problem
        11/3/2017Listed for sale$5,950,000$1,417/sqft
        Source: Keller Williams Key West Compass Realty #577304 Report a problem
        6/1/2017Listing removed$5,950,000$1,417/sqft
        Source: Compass Realty (KW) #572689 Report a problem
        11/10/2016Listed for sale$5,950,000+1703%$1,417/sqft
        Source: Compass Realty (KW) #572689 Report a problem
        4/28/1997Sold$330,000$79/sqft
        Source: Public Record Report a problem

        Public tax history

        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

        BuyAbility℠ payment

        Est. payment
        $41,728/mo
        Principal & interest
        $33642
        Property taxes
        $4681
        HOA Fees
        $3405
        More affordability tools

          Climate risks

          Neighborhood: Truman Annex

          Getting around

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

          Nearby schools

          GreatSchools rating

          Local experts in 33040

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