314 Simonton Street, Key West, FL 33040

$4,950,000

Property Type: Commercial Sale Bedrooms: 8 Baths: 11 Square Footage: 8,472 Lot Size (sq. ft.): 7,750 Status: Contingent

Current Price: $4,950,000 List Date: 11/06/2024 Last Modified: 4/28/2026

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: $4,950,000 Listing Date: 2024-11-05 List Price: $4,950,000

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

Contingent: Contingent Status: Contingent

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: April - 28 - 2026

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.

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