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Casa Antigua

$5,500,000

314 Simonton St, Key West, FL 33040

Active
Last Updated: 08/29/2025

8,472 sqft

Building Size

0.1779 acres

Lot Area

Details:
Building Size:    8,472 sqft
Lot Area:    0.1779 acres
Class:    C
Units:    9
Year Built:    1921
Floors:    3
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.

Discover the allure of Key West, FL, where history and charm converge in a vibrant tropical setting. Situated in the heart of Old Town, the property offers access to a plethora of attractions such as the historic Duval Street, renowned for its eclectic mix of bars, galleries, and boutiques. Embrace the island life with proximity to the iconic Mallory Square, where daily sunset celebrations and street performers captivate visitors. Immerse in the area's rich maritime history at the Key West Historic Seaport and enjoy a stroll along the picturesque Harbor Walk. With diverse dining options, cultural experiences, and vibrant entertainment, the location promises a dynamic backdrop for any commercial venture.

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