314 Simonton Street, Key West, FL 33040

Key West
Local realty services provided by:Better Homes and Gardens Real Estate Destinations
314 Simonton Street,Key West, FL 33040
$4,950,000
  • 8 Beds
  • 11 Baths
  • 8,472 sq. ft.
  • Multi-family
  • Active
Listed by: team gardner/langley
Office: berkshire hathaway homeservices knight & gardner realty
MLS#:612250
Source:FL_FKBOR

Price summary

  • Price:$4,950,000
  • Price per sq. ft.:$584.28

About this home

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.

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Home facts

  • Year built:1921
  • Listing ID #:612250
  • Added:540 day(s) ago
  • Updated:May 09, 2026 at 02:50 PM

Rooms and interior

  • Bedrooms:8
  • Total bathrooms:11
  • Living area:8,472 sq. ft.

Structure and exterior

  • Year built:1921
  • Building area:8,472 sq. ft.
  • Lot area:0.18 Acres
  • Construction Materials:Combo Construction

Finances and disclosures

  • Price:$4,950,000
  • Price per sq. ft.:$584.28
  • Tax amount:$13,667

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