314 Simonton St Key West, FL 33040
Old Town NeighborhoodEstimated payment $31,515/month
Total Views
15,422
8
Beds
11
Baths
8,472
Sq Ft
$649
Price per Sq Ft
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
Map
Property Details
Home Type
Multi-Family
Est. Annual Taxes
$13,668
Year Built
1921
Lot Details
0
Listing Details
- Property Type: Residential
- Style: Multi-Units
- As Is Right To Inspect: Yes
- First Right of Refusal: No
- Mandatory HOA: No
- Fee Includes: None
- Key Island: Key West
- K W Neighborhood: Old Town-N of Truman
- Limited Representation: No
- Marathon Neighborhood: N/A
- Mile Marker: 1.00
- Min Rental Days: 30.00
- M L S Identifier: 20060123165453488875000000
- Off Shore Island: No
- Pets: Pets Allowed
- Property Group I D: 19990816212109142258000000
- Side: Median
- State Province: FL
- Taxes: 13667.88
- Year Built: 1921
- Alternate Key Number: 1004383
- Building Style: Other Bldg Style
- Lot Sq Ft: 7750.00
- Pool Info: In Ground, Concrete
- Species List: No
- Tax Exemptions: None
- Building Style Above Flood: Unknown
- Building Style Stories: 3 Stories
- Estimated Living Sq Ft: 8472.00
- Sewer Hook Up: Yes
- Statistical Purposes Only: No
- Special Features: None
- Property Sub Type: MultiFamily
- Stories: 3
Interior Features
- Total Bathrooms: 11.00
- Full Bathrooms: 7
- Half Bathrooms: 4
- Windows/Doors: Sliding Glass Doors
- Appliances Other: YES
- Total Bedrooms: 8
Exterior Features
- Dockage: None
- Waterfront: None
- Waterfront: No
- Construction: Combo Construction
- Roof: Metal Roof
- Waterview: No Waterview
- Pool: Yes
Utilities
- Utilities: FKAA, Municipal Sewer
Lot Info
- Deed Restrictions: Unknown
- Flood Zone: 0.2 PCT ANNUAL CHANC
- Parcel Number: 00004210-000000
- Land Size: Less Than 1/4 Acre
- Acres: 0.18
Rental Info
- Rentals Allowed: With Restrictions
Tax Info
- Tax Year: 2023
Multi Family
- Total Units: 8.00
Create a Home Valuation Report for This Property
The Home Valuation Report is an in-depth analysis detailing your home's value as well as a comparison with similar homes in the area
Home Values in the Area
Average Home Value in this Area
Tax History
| 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 |
|---|---|---|---|---|
| 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 |
Source: Public Records
Property History
| Date | Event | Price | Change | Sq Ft Price |
|---|---|---|---|---|
| 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 |
Source: Key West Association of REALTORS®
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Special Warranty Deed | -- | Attorney | |
| Interfamily Deed Transfer | -- | Attorney | |
| Deed | $30,000 | -- |
Source: Public Records
Similar Homes in Key West, FL
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.
Nearby Homes
- 421-423 Simonton St
- 616 Eaton St
- 215 Whitehead St
- 709 Eaton St
- 308 Peacon Ln
- 525 Simonton St
- 723 Eaton St
- 202 Admirals Ln
- 416 Appelrouth Ln
- 106 Admirals Ln
- 312 William St
- 408 William St
- 102 Admirals Ln
- 100 Admirals Ln
- 728 Love Ln
- 617 Front St Unit A54/Week 49
- 101 Admirals Ln
- 611 Simonton St
- 216 Fleming St
- 212 Fleming St
- 710 Caroline St
- 417 Southard St Unit B
- 417 Southard St Unit A
- 600 Whitehead St Unit C-4
- 400 Aronovitz Ln
- 1022 Fleming St Unit Lower
- 709 Emma St Unit 1
- 908 Elizabeth St Unit 4
- 844 Olivia St
- 750 Fort St
- 1209 William St Unit 1
- 1114 White St Unit 2
- 1324 Seminary St Unit B
- 1324 Seminary St Unit 1324 Seminary St
- 1504 Flagler Ave
- 1504 Flagler Ave
- 2120 Patterson Ave
- 2001 Flagler Ave
- 2102 Staples Ave
- 2214 Seidenberg Ave