Property
$5,250,0000.18 Acres8 beds • 7 baths • 4 half baths • 8,472 sq ft
For Sale
For Sale
$5,250,0000.18 Acres
For Sale
8 beds • 7 baths • 4 half baths • 8,472 sq ft

314 Simonton Street, Key West, FL 33040 - Monroe County

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Property ID 22006901

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Multi-family - Key West, FL

Description

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.

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.

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Source:First Street
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Source: ListHub, MLS# 612250
Listing status: Active
Listing last updated: January 12, 2026 at 2:37 PM
Listing last checked: January 12, 2026 at 2:30 PM
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