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.
Under contract
Price cut: $300K (4/25)
$4,950,000
314 Simonton St, Key West, FL 33040
8beds
8,472sqft
Multi Family
Built in 1921
-- sqft lot
$-- Zestimate®
$584/sqft
$-- HOA
What's special
- 587 days |
- 265 |
- 10 |
Zillow last checked:
Listing updated:
Listed by:
Team Gardner/Langley 305-902-2447,
Berkshire Hathaway HomeServices Knight & Gardner Realty
Source: FLKMLS,MLS#: 612250
Originating MLS: Key West Association
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 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: $584/sqft
- Annual tax amount: $13,667
- Date on market: 11/14/2024
Estimated market value
Not available
Estimated sales range
Not available
$3,151/mo
Price history
| Date | Event | Price |
|---|---|---|
| 4/28/2026 | Contingent | $4,950,000$584/sqft |
Source: | ||
| 4/25/2026 | Price change | $4,950,000-5.7%$584/sqft |
Source: | ||
| 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$814/sqft |
Source: | ||
Public tax history
Tax history is unavailable.
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: Historic Seaport
Nearby schools
GreatSchools rating
- 4/10Gerald Adams Elementary SchoolGrades: PK-5Distance: 4 mi
- NAMonroe Virtual Instruction ProgramGrades: K-12Distance: 0.5 mi
- 4/10Key West High SchoolGrades: 9-12Distance: 1.7 mi
A local agent can set up tours, give advice and negotiate with sellers.
- Florida
- Monroe County
- Key West
- 33040
- Historic Seaport
- 314 Simonton St






