314 Simonton Street STREET
KEY WEST, FL 33040
8
Bed
11
Bath
8,472Sqft
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 commercia
Property Details
Map
Map
What's Nearby
Nearby Areas
Features
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Bedroom Information
Total Bedrooms: 8Bathroom Information
Total Baths: 11 Full Baths: 7 Half Baths: 4 -
Interior Features
Appliances Other: YES -
Roofing Information
Metal RoofHeating & Cooling
Water Front: No None No WaterviewWindow Information
Window Treatments: Sliding Glass Doors
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Building Information
Year Built: 1921 Total Units: 8.00 Floor Location: 7750 Construction: Combo Construction Roof: Metal Roof -
Pool Information
In Ground,Concrete
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Lot Information
Lot SqFt: 7,750 Lot SqFt Source: Property Data Card 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 -
Property Information
SQ ft (Living Area): 8,472 View: No Waterview Subdivision: Old Town - Unlisted (1.0) Stories: 3 Stories
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Listing Price Information
List Price: $4,950,000
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Tax Information
Taxes: $13,668 Tax Year: 2023 Parcel Number: 00004210-000000 Tax Exemptions: None
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Multi-Unit Information
Pets Allowed: Pets Allowed -
Homeowners Association Information
Mandatory Home Owners Asc: No 1st Right of Refusal: No Association Fee: $0.00
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Utility Information
FKAA,Municipal Sewer
How much is this property worth?
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Nearby Home Value
| Address | Estimate | Bed | Bath | Sq. Ft | Lot Size |
|---|---|---|---|---|---|
| 1440 17th Street, Key West, FL, 33040 | $925,000 | 3 | 2 | 1,211 | 1,211 SqFt |
| 1409 4th Street, Key West, FL, 33040 | $1,250,000 | 4 | 3 | 2,664 | 2,664 SqFt |
| 1614 Dennis Street, Key West, FL, 33040 | $1,299,000 | 7 | 4 | 2,699 | 2,699 SqFt |
| 2004 Patterson Avenue, Key West, FL, 33040 | $925,000 | 4 | 3 | 1,239 | 1,239 SqFt |
| 2016 Roosevelt Drive, Key West, FL, 33040 | $1,300,000 | 7 | 5 | 2,957 | 2,957 SqFt |
| 1612 Laird Street, Key West, FL, 33040 | $1,354,000 | 3 | 3 | 1,904 | 1,904 SqFt |
| 1505 Rose Street, Key West, FL, 33040 | $1,785,000 | 4 | 3 | 1,932 | 1,932 SqFt |
| 1209 Pearl Street, Key West, FL, 33040 | $1,174,000 | 3 | 2 | 1,395 | 1,395 SqFt |
| 1432 Eliza Street, Key West, FL, 33040 | $849,000 | 5 | 2 | 1,501 | 1,501 SqFt |
| 901 Eisenhower Drive, Key West, FL, 33040 | $4,750,000 | 6 | 5 | 3,788 | 3,788 SqFt |
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ByOwner last updated this listing 06/07/2026 @ 16:31
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