$5,250,000

$2M PRICE DROP

314 Simonton St Key West, FL 33040

Old Town Neighborhood

Estimated payment $28,441/month

Total Views 30,413

8 Beds

11 Baths

8,472 Sq Ft

$620 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

Claude Gardner

Berkshire Hathaway HomeServices Knight & Gardner Realty License #BK612006 Listed on: 11/14/2024

Map

Property Details

Home Type

Multi-Family

Year Built

1921

Lot Details

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

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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
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

Source: Public Records

Property History

Date	Event	Price	List to Sale	Price per 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®

Purchase History

Type	Sale Price	Title Company
Special Warranty Deed	--	Attorney
Interfamily Deed Transfer	--	Attorney
Deed	$30,000	--

Source: Public Records

Source: Key West Association of REALTORS®

MLS Number: 612250

APN: 00004210-000000

Florida Monroe County Key West 33040 Old Town

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