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314 Simonton Street, Key West, FL 33040

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For Sale

$5,900,000

8 beds • 7 baths • 4 half baths • 8,472 sqft

Estimated Payment

$      /mo. †

APR for 30 years

Change Loan Terms

  • Multi-Family (2-4 Units)
    Property type

  • $696.41
    Price per square foot

  • Over 50 Years Old
    Age

Explore this Property

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.
MLS# 612250

Courtesy Of Berkshire Hathaway Keys Real Estate | Knight & Gardner Realty

(305) 294-5155

Property Features

  • Age
    Over 50 Years Old
  • Architecture Style
    Other
  • Lot Size
    0.18 Acres
  • Roof Type
    Metal
  • View Type
    Water

Map and Directions

Directions to 314 Simonton Street, Key West, FL 33040

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(305) 292-2921
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Monthly Payment Breakdown

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Copyright © 2025 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. Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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This information is provided for general informational purposes only and should not be relied on in making any home-buying decisions. School information does not guarantee enrollment. Contact a local real estate professional or the school district(s) for current information on schools. This information is not intended for use in determining a person's eligibility to attend a school or to use or benefit from other city, town or local services.

† Based on a 30-year fixed rate of 3.38% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Interest rates are also subject to credit and property approval based on secondary market guidelines. The rates shown are based on average rates for our best qualified customers. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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