314 Simonton Street, Key West, FL 33040

$4,950,000

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

Current Price: $4,950,000 List Date: 11/14/2024 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# 612250

Contract Information

Listing Board: Key West Association As is Rght to Inspct: Yes Species List: No Current Price: $4,950,000 Listing Date: 2024-11-14 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 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 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

General Property Description

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

Fee Includes

None: 1

Dockage

None: 1

Tax Exemptions

None: 1

Pets

Pets Allowed: 1

Waterfront

None: 1

Waterview

No Waterview: 1

Building Style

Above Flood: Unknown Stories: 3 Stories Other Bldg Style: 1

Windows/Doors

Sliding Glass Doors: 1

Construction

Combo Construction: 1

Land Size

Less Than 1/4 Acre: 1

Utilities

FKAA: 1 Municipal Sewer: 1

Pool Info

In Ground: 1 Concrete: 1

Roof

Metal Roof: 1

Status Change Info

Contingent: Contingent Status: Contingent

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: 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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