314 Simonton St

$5,500,000
Price
8
Beds
8,472 Sq. Ft.
$649 / Sq. Ft.
8,472
Sq. Ft.
$649
per Sq. Ft.

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...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.
  1. Listed by Team Gardner/Langley • Berkshire Hathaway HomeServices Knight & Gardner Realty

Property Details for 314 Simonton Street

Waterfront
None
Waterfront
No
Zoning
HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med
Subdivision
Old Town - Unlisted (1.0)
Building Style
Other Bldg Style
Pets
Pets Allowed
LISTING UPDATED: 10/27/2025 10:16 AM

Property Details for 314 Simonton Street

StatusActive
MLS #612250
Days on Market406
Taxes$13,668 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeMulti Family
MLS TypeResidential / Multi-Units
Year Built1921
Lot Size0.18 AC / 7,750 SF
CountyMonroe County

Location

Listing Courtesy of Berkshire Hathaway HomeServices Knight & Gardner Realty
Add your commute

Building Information for 314 Simonton Street

Stories3Residences8Year Built1921Building Size-Lot Size0.18 AC / 7,750 SF

Payment Calculator

$28,316 per month

30 year fixed, 6.28% Interest

Principal and Interest

$27,177

Property Taxes

$1,139

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 314 Simonton Street

Summary
Location and General Information
  • Waterview: No Waterview
  • Area: 02 - Key West
  • Absolute Longitude: 81.803104
  • Control Depth: 0
  • Off Shore Island: No
  • Listing Board: Key West Association
  • Side: Median
  • KW Neighborhood: Old Town-N of Truman
  • Mile Marker: 1.0
  • Marathon Neighborhood: N/A
  • Key/Island: Key West
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: No
  • Association Info: 1st Right of Refusal: No
  • Fee Includes: None
  • Tax Year: 2023
  • Tax Exemptions: None
Property
Lot Information
  • Acres: 0.18
  • Parcel #: 00004210-000000
  • Land Size: Less Than 1/4 Acre
Property and Assessments
  • Legal: 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
  • MLS Approved: Y
  • SqFt Source: Property Data Card
  • Flood Zone: 0.2 PCT ANNUAL CHANC
  • Rentals Allowed: With Restrictions
  • Deed Restrictions: Unknown
  • Picture Count: 32
  • Document Count: 0
  • Building Style: Above Flood: Unknown
Utilities
  • Utilities: FKAA, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Species List: No
  • Pool: Yes
  • Pool Info: In Ground, Concrete
Interior and Exterior Features
Interior Features
  • Appliances: Other: YES
Exterior Features
  • Roof: Metal Roof
  • Construction: Combo Construction
  • Dockage: None
  • Windows/Doors: Sliding Glass Doors

Property History for 314 Simonton Street

DateEvent & SourcePriceAppreciation
Nov 14, 2024

Price Change

FKMLS #612250

$6,900,000
Nov 14, 2024

Price Change

FKMLS #612250

$6,400,000
Nov 14, 2024

Price Change

FKMLS #612250

$5,900,000
Nov 14, 2024

Listed (Active)

FKMLS #612250

$5,500,000
DateEvent & SourcePrice
11/14/2024

Price Change

FKMLS #612250

$6,900,000
11/14/2024

Price Change

FKMLS #612250

$6,400,000
11/14/2024

Price Change

FKMLS #612250

$5,900,000
11/14/2024

Listed (Active)

FKMLS #612250

$5,500,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 314 Simonton Street

Taxable ValueLand$1,170,657Additions$807,830Total$1,978,487
Tax Record2024$13,814 ($1,151 / month)
Home Facts
Total Finished SqFt5,343 SqFtAbove Grade Finished SqFt5,343 SqFtStories4Lot Size7,863 SqFtStyleMiscellaneous CommercialYear Built1921Year Renovated1998CountyMONROEAPN00004210-000000

Schools near 314 Simonton Street

This home is within Monroe.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - K to 12
Public - 9 to 12
Public - K to 5
Rating
School
Distance
Gerald Adams Elementary School
PublicPK to 5

Monroe Virtual Instruction Program
PublicK to 12

Key West High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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314 Simonton Street is a multi-family home for sale in Key West, FL 33040. This property was listed for sale on November 14, 2024 by Berkshire Hathaway HomeServices Knight & Gardner Realty, it's currently listed at $5,500,000. This listing's school district is Monroe. Nearby schools include Gerald Adams Elementary School, Monroe Virtual Instruction Program and Key West High School. 314 Simonton Street is a 8-bed, 11-bath, 8,472 sqft multi-family home built in 1921.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Berkshire Hathaway HomeServices Knight & Gardner Realty

Based on information from one of the following Multiple Listing Services: Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.