314 Simonton St Key West, FL 33040
Old Town NeighborhoodEstimated payment $27,850/month
Highlights
- 0.18 Acre Lot
- Sliding Doors
- 5-minute walk to Truman Annex Park
About This Home
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.
Listing Agent
Berkshire Hathaway HomeServices Knight & Gardner Realty License #BK612006 Listed on: 11/14/2024
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $13,668
Year Built
- Built in 1921
Lot Details
- 7,750 Sq Ft Lot
- Property is zoned HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med
Home Design
- Metal Roof
Interior Spaces
- 8,472 Sq Ft Home
- 3-Story Property
- Sliding Doors
Bedrooms and Bathrooms
- 8 Bedrooms
Community Details
- Old Town Unlisted Subdivision
Listing and Financial Details
- Assessor Parcel Number 00004210-000000
Map
Home Values in the Area
Average Home Value in this Area
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $13,814 | $1,978,487 | $1,170,657 | $807,830 |
| 2024 | $13,668 | $1,258,571 | -- | -- |
| 2023 | $13,668 | $1,234,434 | $0 | $0 |
| 2022 | $13,318 | $1,222,051 | $0 | $0 |
| 2021 | $13,605 | $1,203,995 | $0 | $0 |
| 2020 | $13,590 | $1,210,719 | $0 | $0 |
| 2019 | $13,540 | $1,197,374 | $0 | $0 |
| 2018 | $13,447 | $1,169,319 | $0 | $0 |
| 2017 | $10,650 | $1,157,608 | $0 | $0 |
| 2016 | $11,219 | $1,154,139 | $0 | $0 |
| 2015 | $11,619 | $1,164,465 | $0 | $0 |
| 2014 | $11,950 | $1,151,248 | $0 | $0 |
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 04/25/2026 04/25/26 | Price Changed | $4,950,000 | -5.7% | $584 / Sq Ft |
| 04/08/2026 04/08/26 | Price Changed | $5,250,000 | +2.9% | $620 / Sq Ft |
| 04/08/2026 04/08/26 | Price Changed | $5,100,000 | -2.9% | $602 / Sq Ft |
| 01/12/2026 01/12/26 | Price Changed | $5,250,000 | -4.5% | $620 / Sq Ft |
| 07/28/2025 07/28/25 | Price Changed | $5,500,000 | -6.8% | $649 / Sq Ft |
| 05/20/2025 05/20/25 | Price Changed | $5,900,000 | -7.8% | $696 / Sq Ft |
| 04/01/2025 04/01/25 | Price Changed | $6,400,000 | -7.2% | $755 / Sq Ft |
| 11/14/2024 11/14/24 | For Sale | $6,900,000 | -- | $814 / Sq Ft |
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Special Warranty Deed | -- | Attorney | |
| Interfamily Deed Transfer | -- | Attorney | |
| Deed | $30,000 | -- |
Source: Key West Association of REALTORS®
MLS Number: 612250
APN: 00004210-000000
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
- 616 Caroline St Unit 6
- 616 Eaton St
- 419 Simonton St Unit C
- 617 Fleming St Unit 4
- 709 Eaton St
- 723 Eaton St
- 141 Simonton St
- 317 Whitehead St
- 525 Simonton St
- 119 Simonton St
- 529 Simonton St
- 524 Southard St
- 817 Eaton St Unit 1
- 617 Front St Unit B-51 Penthouse Week
- 617 Front St Unit A52 Penthouse Week 3
- 617 Front St Unit C41 Week 50
- 617 Front St Unit B-24 Week 45
- 617 Front St Unit A-52 Penthouse Week
- 617 Front St Unit C-54 Penthouse Wk 36
- 617 Front St Unit E-43 AB Week 46 Lock
- 536 Fleming St Unit SI FL2-ID1297611P
- 825 Eaton St Unit C
- 725 Southard St
- 327 Margaret St
- 629 Elizabeth St Unit SI ID1297833P
- 918 Southard St Unit 205, Unit 205
- 816 Center St
- 120 Angela St Unit SI ID1384034P
- 717 Emma St Unit A
- 717 Emma St Unit 717-B Emma
- 415 Julia St
- 750 Fort St
- 818 White St Unit 5
- 634 Louisa St
- 1113 Grinnell St
- 1315 Whitehead St Unit SI ID1297834P
- 1209 Pearl St Unit 1209 Pearl Downstairs
- 1505 White St Unit Efficiency
- 8 Hilton Haven Rd
- 2102 Staples Ave
Ask me questions while you tour the home.