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: $250K (1/12)
$5,250,000
314 Simonton St, Key West, FL 33040
8beds
8,472sqft
Est.:
Multi Family
Built in 1921
-- sqft lot
$-- Zestimate®
$620/sqft
$-- HOA
What's special
- 496 days |
- 4,387 |
- 154 |
Zillow last checked: 7 hours ago
Listing updated: January 12, 2026 at 03:20am
Listed by:
Team Gardner/Langley 305-902-2447,
Berkshire Hathaway HomeServices Knight & Gardner Realty
Source: FLKMLS,MLS#: 612250
Originating MLS: Key West Association
Tour with a local 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: $620/sqft
- Annual tax amount: $13,667
- Date on market: 11/14/2024
Estimated market value
Not available
Estimated sales range
Not available
$3,447/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 1/12/2026 | Price change | $5,250,000-4.5%$620/sqft |
Source: | ||
| 7/28/2025 | Price change | $5,500,000-6.8%$649/sqft |
Source: | ||
| 5/20/2025 | Price change | $5,900,000-7.8%$696/sqft |
Source: | ||
| 4/1/2025 | Price change | $6,400,000-7.2%$755/sqft |
Source: | ||
| 11/14/2024 | Listed for sale | $6,900,000$814/sqft |
Source: | ||
Public tax history
Public tax history
Tax history is unavailable.BuyAbility℠ payment
Est. payment
$30,328/mo
Principal & interest
$26741
Property taxes
$3587
More affordability tools
Climate risks
Neighborhood: Historic Seaport
Nearby schools
GreatSchools rating
- 4/10Gerald Adams Elementary SchoolGrades: PK-5Distance: 3.9 mi
- NAMonroe Virtual FranchiseGrades: K,2-3,5-12Distance: 0.5 mi
- 3/10Key West High SchoolGrades: 9-12Distance: 1.7 mi
Local experts in 33040
- Florida
- Monroe County
- Key West
- 33040
- Historic Seaport
- 314 Simonton St







