314 Simonton Street, Key West, FL 33040

$4,500,000

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

Current Price: $4,500,000 List Date: 11/14/2024 Last Modified: 7/06/2026

Overview

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.

Listing Details MLS# 612250

Location, Tax & Legal

Street #: 314
Street Name: Simonton
Street Suffix: Street
Key/Island: Key West
State/Province: FL
Zip Code: 33040
County: Monroe
Subdivision: Old Town - Unlisted (1.0)
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
Deed Restrictions: Unknown
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
Pub Sewer HkUp: Yes

Contract Information

Listing Board: Key West Association
As is Rght to Inspct: Yes
Species List: No

General Property Description

Realtor.COM Type: Multi-family
Style: Multi-Units
Waterfront: No
Pool: Yes
Year Built: 1921
Total Units: 8
Lot SqFt: 7750
Lot Sqft Source: Property Data Card
Acres: 0.18
Living Apx SqFt: 8472
SqFt Source: Property Data Card
Total Bedrooms: 8
Full Baths: 7
Half Baths: 4
Total Baths: 11
Rentals Allowed: With Restrictions
Min Rental Days: 30
Control Depth: 0

Status Change Info

Under Contract Date: 2026-07-01
Sold Date: 2026-07-06

Association Info

Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0

Building Style

Above Flood: Unknown
Stories: 3 Stories
Other Bldg Style: Yes

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.

Fee Includes

None: Yes

Dockage

None: Yes

Tax Exemptions

None: Yes

Pets

Pets Allowed: Yes

Waterfront

None: Yes

Waterview

No Waterview: Yes

Windows/Doors

Sliding Glass Doors: Yes

Construction

Combo Construction: Yes

Land Size

Less Than 1/4 Acre: Yes

Utilities

FKAA: Yes
Municipal Sewer: Yes

Pool Info

In Ground: Yes
Concrete: Yes

Roof

Metal Roof: Yes

Property Features

Fee Includes: None Tax Exemptions: None Waterfront: None Waterview: No Waterview Dockage: None Building Style: Other Bldg Style Utilities: FKAA; Municipal Sewer Pool Info: In Ground; Concrete Construction: Combo Construction Roof: Metal Roof Pets: Pets Allowed Land Size: Less Than 1/4 Acre

Listing Office: Berkshire Hathaway HomeServices Knight & Gardner Realty

Last Updated: July - 06 - 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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