314 Simonton St, Key West, FL 33040

$4,500,000
8
BD
11
BA
8,472
SqFt

Show Photos

Verify your account to unlock exclusive photos, mortgage tools, and more.

Sold Price
$4,500,000
List Price
$4,950,000
MLS#
612250
Days on Market
599
Closing Date
Jul 06, 2026
Year Built
1921
Style
Other
Bedrooms
8
Bathrooms
11
Half-baths
4
Acres
0.18
Living Area
8,472
Region
Key West
Neighborhood
Old Town-N of Truman
Subdivision
Old Town - Unlisted (1.0)

Property 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.

Additional Information

Lot Size
7,750
Roof
Metal
Pool
Yes

Mortgage Calculator

Amount of Loan
Annual Interest Rate
%
Term of Loan
Years

Does not include any taxes or fees.
Please consult a financial professional.
Calculator source: Real Geeks

Listing courtesy of Berkshire Hathaway HomeServices Knight & Gardner Realty. Selling Office: .