Date
Details
Price
Change
Source
11/05/2024
Listed
$4,950,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/32
$4,950,000 Contingent
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/32
Property 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.
Full Property Details
Full Property Details for 314 Simonton St
General
- Price: $4,950,000
- Taxes: $13,667 (2023)
- Status: Contingent
- Type: Commercial
- Source: 927
- MLS ID: 612134
- Updated: 5/13/2026
- Added to Site: 558 day(s) ago
Interior
- Interior Features: Laundry Room, Other
- Flooring: Combo
Rooms
Bathrooms
- Total Bathrooms: 11
- Full Bathrooms: 7
- Half Bathrooms: 4
Bedrooms
- Total Bedrooms: 8
Parking
- Total Spaces: 2
- Parking Features: Off Street, Covered
Location
- Area: 02 - Key West
- County: Monroe
- Subdivision: Old Town - Unlisted (1.0)
Community
- Assoc. Fees Include: None
Heating & Cooling
- Air Conditioning: Yes
- Cooling Type: Wall/Window Unit(s), Ceiling Fans(s)
Structural Information
- # Buildings: 1
- Construction: Combo Construction
- Windows/Doors: Sliding Glass Doors
- Stories/Levels: 3
- Square Feet: 8,472
- Sq. Ft. Source: Property Data Card
- Year Built: 1921
Unit Information
- Units in Building: 8
Lot Features
- Property View: No Waterview
- Lot Size (Acres): 0.18
- Lot Size (Sq. Ft.): 7,750
- Lot Dimensions: 50 x 156
- Zoning: HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med
Water Features
- Water View: Yes
Financial Considerations
- Tax Amount: $13,667.88
- Tax Year: 2023
Disclosures and Reports
- Legal Description: 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
- Flood Zone: 0.2 PCT ANNUAL CHANC
- APN: 00004210-000000
Listed by Berkshire Hathaway HomeServices Knight & Gardner Realty, Team Gardner/Langley (305) 902-2447
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agent
— 314 Simonton St —
Team Gardner/Langley
Berkshire Hathaway HomeServices Knight & Gardner Realty
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 314 Simonton St
School District:Monroe County School District, Middle Torch Key, FL
| Name | Grades | Distance |
|---|---|---|
Horace O'bryant School 1105 Leon Street, Key West, FL 33040 | 6-8 | 1.1 mi |
Gerald Adams Elementary School 5855 College Road, Key West, FL 33040 | PK-5 | 3.9 mi |
Key West High School 2100 Flagler Avenue, Key West, FL 33040 | 9-12 | 1.7 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 314 Simonton St
Tax History
Tax History for 314 Simonton St
Year
Property Taxes
Change
Tax Assessment
Change
2024
$13,814
—
$1,978,487
57%
2024
$13,814
1%
$1,258,571
2%
2023
$13,668
—
$1,234,434
3%
2021
$13,605
2%
$1,203,995
-1%
2022
$13,318
-2%
$1,222,051
1%
2021
$13,605
—
$1,210,719
1%
2019
$13,540
1%
$1,197,374
2%
2018
$13,447
26%
$1,169,319
1%
2017
$10,650
-5%
$1,157,608
—
2016
$11,218
-3%
$1,154,139
-1%
2015
$11,619
-3%
$1,164,465
1%
2014
$11,950
2%
$1,151,248
3%
2013
$11,699
—
$1,112,994
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 314 Simonton St
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
- Mobile Home
- Active
- Updated 2 days ago
- 3Beds
- 3Total Baths
- 1,222Sq. Ft.
- Single Family
- Active
- Updated 2 days ago
- 2Beds
- 2Total Baths
- 1,344Sq. Ft.
- Single Family
- Active
- Updated 3 days ago
- 4Beds
- 4Total Baths
- 2,409Sq. Ft.
- Single Family
- Active
- Updated 2 days ago
- 3Beds
- 2Total Baths
- 1,548Sq. Ft.
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
- Single Family
- Active
- Updated 2 days ago
- 3Beds
- 2Total Baths
- 1,968Sq. Ft.
- Single Family
- Active
- Updated 3 days ago
- 3Beds
- 2Total Baths
- 1,376Sq. Ft.
- Single Family
- Active
- Updated 3 days ago
- 8Beds
- 4Total Baths
- 4,681Sq. Ft.
- Single Family
- Active
- Updated 3 days ago
- 3Beds
- 3Total Baths
- 1,667Sq. Ft.
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
- Single Family
- Closed
- Updated 2 days ago
- 4Beds
- 4Total Baths
- 3,026Sq. Ft.
- Single Family
- Closed
- Updated 1 day ago
- 5Beds
- 6Total Baths
- 3,434Sq. Ft.
- Single Family
- Closed
- Updated 2 days ago
- 4Beds
- 5Total Baths
- 3,624Sq. Ft.
- Single Family
- Closed
- Updated 2 days ago
- 5Beds
- 6Total Baths
- 3,650Sq. Ft.
314 Simonton Street, Key West, FL 33040 (MLS# 612134) is a Commercial property. 314 Simonton Street is currently listed for $4,950,000 and was received on November 05, 2024. Want to learn more about 314 Simonton Street? Do you have questions about finding other Commercial real estate for sale in Key West? You can browse all Key West real estate or contact a Coldwell Banker agent to request more information.