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103 Front Street
Key West FL 33040 US

$6,850,000

Active Listing ID 617136
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3 bed
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3.00 Bath (3 Full)
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Lot: 0.20 Acres
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Single Family Residence

$6,850,000

Active Listing ID 617136
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103 Front Street 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.

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Property Features

  • Facts
  • Lot Size: 0.20 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 3
  • Cooling System: Central Air
  • Exterior Finish: Fencing, Lighting, Outdoor Shower, Sprinkler System, Storage, Water Display
  • Floor Covering: Wood, Marble
  • Roof Type: Metal
  • Additional Features
  • Patio
  • Pool

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 6850000
  • unparsedaddress: 103 Front Street
  • postalcity: Key West
  • stateorprovince: FL
  • country: US
  • postalcode: 33040
  • bathroomsfull: 3
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.2
  • lotsizeunits: Acres
  • lotsizearea: 0.2
  • livingarea: 3000
  • livingareaunits: Square Feet
  • latitude: 24.55581
  • longitude: -81.80686
  • listagentfullname: Laura A McChesney
  • listagentemail: mcchesneykeywest@aol.com
  • listagentkey: 3yd-KWARFL-20080326130928572380000000
  • listagentmlsid: kwa.1165
  • listagentpreferredphone: 3059236639
  • listofficekey: 3yd-KWARFL-20070803221403061445000000
  • listofficemlsid: kwa.10104
  • disclaimer: Copyright © 2026 Key West Association of Realtors. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
  • sourcesystemid: KWARFL
  • yearbuilt: 1918
  • listingcontractdate: 2025-11-01
  • listagenturl: http://www.preferredpropertieskeywest.com
  • countyorparish: Monroe
  • parcelnumber: 00004590-002157
  • appliances: Washer, Dryer, Dishwasher, Refrigerator, Oven, Microwave, Ice Machine
  • cooling: Central Air
  • constructionmaterials: Combo Construction
  • flooring: Wood, Marble
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 2
  • parkingtotal: 0
  • parkingfeatures: Carport, Off Street
  • roof: Metal
  • view: Water
  • waterfrontyn: False
  • franchiseaffiliation: None
  • interiorfeatures: Built-in Cabinets, Granite Counter Top, Security System
  • exteriorfeatures: Fencing, Lighting, Outdoor Shower, Sprinkler System, Storage, Water Display
  • rooms: Bathroom 2, Bedroom 1, Bedroom 3, Bathroom 1, Bedroom 2, Bathroom 3
  • securityfeatures: Security System
  • otherstructures: Storage
  • utilities: Propane
  • patioandporchfeatures: Patio
  • dock: False
  • poolprivateyn: True
  • spayn: False
  • fencing: Fenced
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: False
  • internetconsumercommentyn: False
  • location: -81.80686, 24.55581
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Preferred Properties Coastal Realty, Inc.", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"mcchesneykeywest@aol.com", "ListBrokerageCity":"Key West", "ListBrokerageCountry":"US", "ListBrokerageEmail":"mcchesneykeywest@gmail.com", "ListBrokerageLogoUrl":null, "ListBrokerageName":"Preferred Properties Coastal Realty, Inc.", "ListBrokeragePhone":"(305) 294-3040", "ListBrokeragePostalCode":"33040", "ListBrokerageStateOrProvince":"FL", "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"520 Southard Street", "ListBrokerageWebsiteUrl":"http://www.preferredpropertieskeywest.com/", "ListOfficeAddress1":"520 Southard Street ", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":"20070803221403061445000000", "ListOfficeCity":"Key West", "ListOfficeCountry":"US", "ListOfficeEmail":"info@preferredpropertieskeywest.com", "ListOfficePostalCode":"33040", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"SINGLE_FAMILY - Key West, FL", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/103-Front-St_Key-West_FL_33040_M54977-29865?f=listhub&s=KWARFL&m=617136&c=rexren", "MLSModificationTimestamp":"2026-05-29 16:51:59", "Neighborhoods":[{"Description":null, "Name":"The Foundry (1.0)"}], "PostalCode":null, "RoomCount":null, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":34273, "TaxDescription":"KW PT LOTS 2 & 3 SQR 28 (.2023 AC) OR1307-1729 OR1307-1732/35 OR1307-1736/39 OR1329-1340/44 OR1331-518/21 OR1332-323/76", "TaxYear":"2024"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 5/29/2026 4:52:54 PM GMT
Source Updated Date: 6/3/2026 6:54:35 PM GMT

Courtesy of: Laura A McChesney, Preferred Properties (KW), mcchesneykeywest@aol.com

Copyright © 2026 Key West Association of Realtors. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.