314 Simonton Street, Key West, FL 33040
$5,500,000
Property Type:
Commercial Sale
Bedrooms:
8
Baths:
11
Square Footage:
8,472
Lot Size (sq. ft.):
7,750
Status:
Active
Current Price:
$5,500,000
List Date:
11/06/2024
Last Modified:
10/27/2025
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.
More Information MLS# 612134
Contract Information
Listing Board: Key West Association
Limited Representation: No
Potential Short Sale: No
Bank Owned: No
For Sale/Lease: For Sale
Current Price: $5,500,000
Listing Date: 2024-11-05
List Price: $5,500,000
Location, Tax & Legal
KW Neighborhood: Old Town-N of Truman
City: KEY WEST
Off Shore Island: No
Mile Marker: 1
Marathon Neighborhood: N/A
Side: Median
Flood Zone: 0.2 PCT ANNUAL CHANC
Alternate Key #: 1004383
Parcel #: 00004210-000000
Zoning: HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med
Legal: KW PT LT 2 SQR 24 OR252-75/76 OR625-467/68 OR742-76 OR845-822 OR1648-526/27 OR2519-148/49 OR2852-2389/90
Taxes: 13667.88
Tax Year: 2023
Street #: 314
Street Name: Simonton
Street Suffix: Street
Key/Island: Key West
State/Province: FL
Zip Code: 33040
Subdivision: Old Town - Unlisted (1.0)
County: Monroe
Area: 02 - Key West
General Property Description
Realtor.COM Type: Commercial
Waterfront: No
Control Depth: 0
Lot Size: 50 X 156
Lot SqFt: 7750
Total Units: 8
# Parking Spaces: 2
Off Street Parking: Yes
# Stories: 3
SqFt Source: Property Data Card
Total # Buildings: 1
Building SqFt: 8472
Style: Commercial
Living Apx SqFt: 8472
Year Built: 1921
Total Bedrooms: 8
Full Baths: 7
Half Baths: 4
Total Baths: 11
Remarks & Misc
Remarks – Consumer: 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.
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Type
Apartment 3 or more: 1
Professional Service: 1
Retail: 1
Other Services: 1
Fee Includes
None: 1
Dockage
None: 1
Cooling
Ceiling Fans(s): 1
Wall/Window Unit(s): 1
Waterfront
None: 1
Waterview
No Waterview: 1
Floor
Combo: 1
Interior Features
Laundry Room: 1
Other: 1
Windows/Doors
Sliding Glass Doors: 1
Vehicle Storage
Covered Parking: 1
Off Street Parking: 1
Construction
Combo Construction: 1
Land Size
Less Than 1/4 Acre: 1
Utilities
FKAA: 1
Municipal Sewer: 1
Financial Status
Bank Owned: No
Potential Short Sale: No
Status Change Info
Status: Active
Property Features
Type: Apartment 3 or more; Professional Service; Retail; Other Services
Waterfront: None
Waterview: No Waterview
Dockage: None
Vehicle Storage: Covered Parking; Off Street Parking
Cooling: Ceiling Fans(s); Wall/Window Unit(s)
Utilities: FKAA; Municipal Sewer
Interior Features: Laundry Room; Other
Construction: Combo Construction
Floor: Combo
Land Size: Less Than 1/4 Acre
Fee Includes: None
Listing Office:
Berkshire Hathaway HomeServices Knight & Gardner Realty
Last Updated: October - 27 - 2025
The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.