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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. 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.

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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: Ceiling Fan(s)
  • Exterior Finish: Fencing, Water Display, Storage, Sprinkler System, Outdoor Shower, Lighting
  • Floor Covering: Marble, Wood
  • Roof Type: Metal

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: 4200
  • livingareaunits: Square Feet
  • latitude: 24.55581
  • longitude: -81.80686
  • listagentfullname: Laura A McChesney
  • listagentemail: mcchesneykeywest@aol.com
  • listagentkey: 3yd-KWARFL-20080326130928572380000000
  • listagentmlsid: 20080326130928572380000000
  • listagentpreferredphone: 3059236639
  • listagentofficephone: 3052943040
  • listofficekey: 3yd-KWARFL-20070803221403061445000000
  • listagentstatelicense: 494597
  • listofficemlsid: 20070803221403061445000000
  • 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
  • listagenturl: http://www.preferredpropertieskeywest.com
  • countyorparish: Monroe
  • parcelnumber: 00004590-002157
  • appliances: Dishwasher, Dryer, Microwave, Refrigerator, Washer
  • cooling: Ceiling Fan(s)
  • constructionmaterials: Other
  • flooring: Marble, Wood
  • numberofunitstotal: 0
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 2
  • parkingtotal: 0
  • parkingfeatures: Carport
  • roof: Metal
  • view: Water
  • waterfrontyn: False
  • interiorfeatures: Wet Bar, Built-in Cabinets, Security System, Granite Counter Top, Cathedral Ceilings
  • exteriorfeatures: Fencing, Water Display, Storage, Sprinkler System, Outdoor Shower, Lighting
  • architecturalstyle: Other
  • rooms: Bathroom 1, Bathroom 2, Bathroom 3, Bedroom 1, Bedroom 2, Bedroom 3
  • securityfeatures: Security System
  • otherstructures: Storage
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • fencing: Fenced
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -81.80686, 24.55581
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Preferred Properties Coastal Realty, Inc.", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "Expenses":[{"ExpenseCategory":"Home Owner Assessments Fee", "ExpenseFrequency":"Quarterly", "ExpenseValue":10214}], "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":"20080326130928572380000000", "ListOfficeCity":"Key West", "ListOfficeCountry":"US", "ListOfficeEmail":"info@preferredpropertieskeywest.com", "ListOfficePostalCode":"33040", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"Residential - 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":"2025-11-01T13:16:09Z", "Neighborhoods":[{"Description":null, "Name":"01 - Key West"}], "PostalCode":null, "RawPropertySubType":"Residential - Single Family", "RawPropertyType":"Residential", "RoomCount":null, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":34272.76, "TaxDescription":null, "TaxYear":"2024"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 1/1/2026 1:23:32 AM GMT
Source Updated Date: 1/11/2026 6:42:41 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.