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.
For sale
Price cut: $400K (7/28)
$5,500,000
314 Simonton St, Key West, FL 33040
8beds
8,472sqft
Est.:
Multi Family
Built in 1921
-- sqft lot
$-- Zestimate®
$649/sqft
$-- HOA
What's special
- 270 days
- on Zillow |
- 4,153 |
- 224 |
Zillow last checked: 7 hours ago
Listing updated: July 28, 2025 at 12:08am
Listed by:
Team Gardner/Langley 305-902-2447,
Berkshire Hathaway HomeServices Knight & Gardner Realty
Source: FLKMLS,MLS#: 612250
Originating MLS: Key West Association

Travel times
Tour with a buyer's agent
Tour with a buyer's agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 8
- Bathrooms: 11
- Full bathrooms: 7
- 1/2 bathrooms: 4
Appliances
- Included: YES
Features
- Doors: Sliding Glass Doors
Interior area
- Total interior livable area: 8,472 sqft
Property
Features
- Levels: 3 Stories
- Stories: 3
- Has private pool: Yes
- Pool features: In Ground, Concrete
- Water view: None
- Waterfront features: None, Dockage: None
Lot
- Size: 7,840.8 Square Feet
- Features: Less Than 1/4 Acre
Details
- Parcel number: 00004210000000
- Zoning: HNC
- Zoning description: (1-3) Hist Nghborhd Comml 1 - 3 Coastal Med
Construction
Type & style
- Home type: MultiFamily
- Architectural style: Other Bldg Style
- Property subtype: Multi Family
Materials
- Combo Construction
- Roof: Metal
Condition
- Year built: 1921
Utilities & green energy
- Sewer: Municipal Sewer, Public Sewer
- Utilities for property: FKAA
Community & HOA
Community
- Subdivision: Old Town - Unlisted (1.0)
HOA
- Has HOA: No
- Services included: None
Location
- Region: Key West
Financial & listing details
- Price per square foot: $649/sqft
- Annual tax amount: $13,667
- Date on market: 11/14/2024
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