Shane Wilson
Responds Quickly
Cypress Realty, Inc.
(239) 341-5344
121 Total Sales
3 in Old Town
$1.4M - $2M Price Range
314 Simonton St Key West, FL 33040
Old Town Neighborhood
8
Beds
11
Baths
8,472
Sq Ft
7,750
Sq Ft Lot
Highlights
- 0.18 Acre Lot
- Sliding Doors
- 5-minute walk to Truman Annex Park
About This Home
As of July 2026Step 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.
Last Agent to Sell the Property
Berkshire Hathaway HomeServices Knight & Gardner Realty License #BK612006 Listed on: 11/14/2024
Last Buyer's Agent
Berkshire Hathaway HomeServices Knight & Gardner Realty License #3537722
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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
- Sliding Doors
Bedrooms and Bathrooms
- 8 Bedrooms
Community Details
- Old Town Unlisted Subdivision
Listing and Financial Details
- Assessor Parcel Number 00004210-000000
Ownership 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
Name
Owned For
Owner Type
Purchase Details
Listed on
Nov 14, 2024
Closed on
Jul 6, 2026
Sold by
Nicole Crummitt Racquel and Nicole Crummitt Raquel
Bought by
Seller's Agent
Claude Gardner
Berkshire Hathaway HomeServices Knight & Gardner Realty
Buyer's Agent
Zainya Zimmerer
Berkshire Hathaway HomeServices Knight & Gardner Realty
List Price
$6,900,000
Sold Price
$4,500,000
Premium/Discount to List
-$2,400,000
-34.78%
Views
1001
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
1.87%
Purchase Details
Closed on
Apr 20, 2017
Sold by
Begue Felicia
Bought by
Felicia Michelle Llc
Purchase Details
Closed on
May 16, 2011
Sold by
Worth Mary Ann
Bought by
Worth Mary Ann and Oosterhoudt Allen Thomas
Purchase Details
Closed on
Feb 1, 1975
Bought by
Worth Mary Ann L and Worth E
Home Values in the Area
Average Home Value in this Area
Agents Specializing in Old Town, FL
-
Shane Wilson
-
Bernice Schafer
Bernice Schafer
Vested Palm Real Estate and Home Services
(888) 614-9574
59 Total Sales
25 in Old Town
$115K - $4.5M Price Range
-
Lindsay Ryan
Lindsay Ryan
EXP Realty LLC
(786) 751-4493
59 Total Sales
5 in Old Town
$840K - $4.8M Price Range
-
Anneliese Dietrick
Anneliese Dietrick
Coldwell Banker Schmitt Lower Keys (KW)
(844) 666-4591
37 Total Sales
2 in Old Town
$1.1M - $2.9M Price Range
-
Mike Kane
Mike Kane
Internet Realty of the Florida Keys
(703) 884-2537
25 Total Sales
5 in Old Town
$750K - $910K Price Range
-
Austin Kimbler
Austin Kimbler
Expert Realty LLC (HQ)
(786) 901-8149
48 Total Sales
6 in Old Town
$850K - $3.7M Price Range
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: Public Records
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 |
|---|---|---|---|---|
| 07/06/2026 07/06/26 | Sold | $4,500,000 | -9.1% | $531 / 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 |
Source: Key West Association of REALTORS®
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 | $20,788 | $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 |
Source: Public Records
Agents Affiliated with this Home
-
Claude Gardner
Seller's Agent in 2026
Claude Gardner
Berkshire Hathaway HomeServices Knight & Gardner Realty
(305) 902-2447
134 in this area
263 Total Sales
-
Zainya Zimmerer
Buyer's Agent in 2026
Zainya Zimmerer
Berkshire Hathaway HomeServices Knight & Gardner Realty
(305) 240-5476
8 in this area
19 Total Sales
Map
Source: Key West Association of REALTORS®
MLS Number: 612250
APN: 00004210-000000
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