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
Closing Date
Jul 06, 2026
MLS#
612250
Style
Other
Status
CLOSED
Island
Key West
County
Monroe
City
Key West
Area
Key West
Subdivision
Old Town - Unlisted (1.0)
Neighborhood
Old Town-N of Truman
Bedrooms
8
Bathrooms
11
Half Baths
4
Living Area
8,472
Acres
0.18
Year Built
1921
Days on Market
599

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

Taxes
$13,667
Roof
Metal
Pool
Yes
Zoning
HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med

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, Contact:

Selling Office: .