314 Simonton Street, Key West, FL 33040

$5,250,000
Property Type: Residential Bedrooms: 8 Baths: 11 Square Footage: 8,472 Lot Size (sq. ft.): 7,750 Status: Active
Current Price: $5,250,000 List Date: 11/14/2024 Last Modified: 1/27/2026

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

Current Price: $5,250,000 Listing Date: 2024-11-14 Listing Board: Key West Association List Price: $5,250,000 As is Rght to Inspct: Yes Species List: No

Location Tax Legal

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 Style: Multi-Units Waterfront: No Pool: Yes Year Built: 1921 Total Units: 8 Lot SqFt: 7750 Lot Sqft Source: Property Data Card Acres: 0.18 Living Apx SqFt: 8472 SqFt Source: Property Data Card Total Bedrooms: 8 Full Baths: 7 Half Baths: 4 Total Baths: 11 Rentals Allowed: With Restrictions Min Rental Days: 30

Status Change Info

Status: Active

Association Info

Mandatory Home Owners Asc: No 1st Right of Refusal: No

Building Style

Above Flood: Unknown Stories: 3 Stories

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: January - 27 - 2026
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