314 Simonton Street, Key West, FL 33040 (MLS# 612250)

314 Simonton Street, Key West, FL 33040

$5,500,000

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

Current Price: $5,500,000 List Date: 11/14/2024 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# 612250

Contract Information

Listing Board: Key West Association As is Rght to Inspct: Yes Species List: No Current Price: $5,500,000 Listing Date: 2024-11-14 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 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

Status: Active

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: October - 27 - 2025

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