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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.
    109 days
    |
    2,604
    |
    68
    |

    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 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
    $41,899/mo
    Principal & interest
    $33813
    Property taxes
    $4681
    HOA Fees
    $3405

      Climate risks

      Neighborhood: Truman Annex

      Nearby schools

      GreatSchools rating

      Local experts in 33040

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