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314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
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314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
314 Simonton Street
Sold

314 Simonton Street

314 Simonton Street, Key West, FL 33040

$4,500,000
Step into Key West history with this remarkable property, available for the first time in generations! Located just a block from world-famous Duval Street and across from the Federal Courthouse, this property at 314 Simonton Street offers a unique blend of historic charm and modern potential. Originally a hotel with a Ford dealership on the ground floor, this three-level building is steeped in heritage. Even the legendary Ernest Hemingway chose it as his base, staying here for a month while awaiting delivery of his car in 1928. Currently set up and legally recognized as 8 units, an atrium, garage, and a pool, this property provides an unmatched opportunity for someone who loves trophy properties. Whether you envision a grand single-family estate or multi-unit living combined with commercial space on the lower level, the possibilities are endless.Don't miss the chance to own a piece of Key West's past while shaping its future with this truly one-of-a-kind property.

8
beds

11
baths

8,472 Sq.Ft. LIVING AREA

7,750 Sq.Ft. lot

Team Gardner/Langley

Team Gardner/Langley

Features & Amenities

Interior

  • total bedrooms8
  • Total bathrooms11
  • full bathrooms7
  • half bathrooms4

Area & Lot

  • Status Sold
  • Date Sold July 6, 2026
  • Living Area8,472 Sq.Ft.
  • Total Area8,472 Sq.Ft.
  • Lot Area7,750 Sq.Ft.
  • MLS® ID612250
  • TypeMulti-Family
  • YEAR BUILT1921
  • NeighborhoodKey West
  • Architecture StylesAbove Flood, Other Bldg Style
  • Water FrontageNone
  • View DescriptionNo Waterview

Exterior

  • PoolConcrete, In Ground
  • roofMetal

Financial

  • Sales Price$4,500,000
  • Real Estate Tax $13,668/yr
  • Zoning HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med

Key West

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