314 Simonton Street, Key West, FL 33040
$5,250,000
Property Type:
Commercial Sale
Bedrooms:
8
Baths:
11
Square Footage:
8,472
Lot Size (sq. ft.):
7,750
Status:
Active
Current Price:
$5,250,000
List Date:
11/06/2024
Last Modified:
4/08/2026
Overview
Description
Listing Details MLS# 612134
Location, Tax & Legal
- 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
- 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
Contract Information
- Listing Board
- Key West Association
- Limited Representation
- No
- For Sale/Lease
- For Sale
- Potential Short Sale
- No
- Bank Owned
- No
General Property Description
- Realtor.COM Type
- Commercial
- Style
- Commercial
- Lot SqFt
- 7750
- Waterfront
- No
- # Parking Spaces
- 2
- Off Street Parking
- Yes
- # Stories
- 3
- Total # Buildings
- Yes
- Building SqFt
- 8472
- SqFt Source
- Property Data Card
- Living Apx SqFt
- 8472
- Total Units
- 8
- Year Built
- 1921
- Total Bedrooms
- 8
- Full Baths
- 7
- Half Baths
- 4
- Total Baths
- 11
- Control Depth
- 0
Association Info
- Mandatory Home Owners Asc
- No
- 1st Right of Refusal
- No
Financial Status
- Bank Owned
- No
- Potential Short Sale
- No
More Information
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.
Type
- Apartment 3 or more
- Yes
- Professional Service
- Yes
- Retail
- Yes
- Other Services
- Yes
Fee Includes
- None
- Yes
Dockage
- None
- Yes
Cooling
- Ceiling Fans(s)
- Yes
- Wall/Window Unit(s)
- Yes
Waterfront
- None
- Yes
Waterview
- No Waterview
- Yes
Floor
- Combo
- Yes
Interior Features
- Laundry Room
- Yes
- Other
- Yes
Windows/Doors
- Sliding Glass Doors
- Yes
Vehicle Storage
- Covered Parking
- Yes
- Off Street Parking
- Yes
Construction
- Combo Construction
- Yes
Land Size
- Less Than 1/4 Acre
- Yes
Utilities
- FKAA
- Yes
- Municipal Sewer
- Yes
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 - 08 - 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.