314 Simonton St, Key West, FL 33040
UNDER CONTRACT

314 Simonton St
Key West, FL 33040

Historic Seaport
  • 8 Beds
  • 9 Baths
  • 8,472 sqft

$4,950,000

Est. Mortgage $28,176/mo*
Get Pre-Qualified

$4,950,000

Est. Mortgage $28,176/mo*
Get Pre-Qualified
8 Beds
9 Baths
8,472 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

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 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.

Home Highlights

Parking
No Info
Outdoor
Pool
View
No Info
HOA
None
Price/Sqft
$584
Listed
180+ days ago

Home Details for 314 Simonton St

Interior Features

Beds & Baths
Number of Bedrooms: 8Number of Bathrooms: 11Number of Bathrooms (full): 7Number of Bathrooms (half): 4
Dimensions and Layout
Living Area: 8472 Square Feet
Appliances & Utilities
Utilities: FKAAAppliances: YES
Windows, Doors, Floors & Walls
Door: Sliding Glass Doors
Levels, Entrance, & Accessibility
Stories: 3Levels: 3 Stories

Exterior Features

Exterior Home Features
Roof: MetalHas a Private Pool
Pool
Pool: In Ground, ConcretePool
Frontage
Waterfront: None, Dockage: NoneNot on Waterfront
Water & Sewer
Sewer: Municipal Sewer, Public Sewer

Days on Market

Days on Market: 180+

Property Information

Year Built
Year Built: 1921
Property Type / Style
Property Type: ResidentialProperty Subtype: Multi FamilyArchitecture: Other Bldg Style
Building
Construction Materials: Combo Construction
Property Information
Parcel Number: 00004210000000

Price & Status

Price
List Price: $4,950,000Price Per Sqft: $584

Active Status

MLS Status: Contingent

Location

Direction & Address
City: Key WestCommunity: Old Town - Unlisted (1.0)

Agent Information

Listing Agent
Listing ID: 612250

HOA

HOA Fee Includes: NoneAssociation for this Listing: Key West AssociationNo HOAHOA Fee: No HOA Fee

Lot Information

Lot Area: 7840.8 sqft

Offer

Contingencies: Contingent

Miscellaneous

Mls Number: 612250Zillow Contingency Status: Under ContractWater View: None
Last check for updates: about 6 hours ago
Listing courtesy of Team Gardner/Langley, (305) 902-2447
Berkshire Hathaway HomeServices Knight & Gardner Realty
Originating MLS: Key West Association
Source: FLKMLS, MLS#612250
Also Listed on FLKMLS, Key West AOR, Key West AOR.

Market trends in Key West

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.14M
$33.33KMoM
Sale-to-List Price
94.5%
0.0%MoM
Price per sq ft
$926
$79MoM
Available listings
304
28MoM

Price History for 314 Simonton St

DatePriceEventSource
04/28/2026$4,950,000ContingentFLKMLS #612250
04/25/2026$4,950,000PriceChange
Key West AOR #612250
01/12/2026$5,250,000PriceChange
Key West AOR #612250
07/28/2025$5,500,000PriceChange
FLKMLS #612250
05/20/2025$5,900,000PriceChange
FLKMLS #612250
04/01/2025$6,400,000PriceChange
Key West AOR #612250
11/14/2024$6,900,000Listed For SaleKey West AOR #612250

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Comparable Sales for 314 Simonton St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
909 & 913 Thomas St, Key West, FL
0.56
Multi-Family Home
$2,000,000
02/27/26
8
8
3,532
720-726 Emma St, Key West, FL
0.51
Multi-Family Home
$1,275,000
05/12/26
8
10
2,432
514 Margaret St, Key West, FL
0.32
Multi-Family Home
$1,400,000
01/14/26
5
3.5
2,068
602 Southard St, Key West, FL
0.25
Multi-Family Home
$1,425,000
07/10/25
3
3
2,671
704 Caroline St, Key West, FL
0.13
Multi-Family Home
$1,750,000
08/05/25
4
5
2,080
708 William St, Key West, FL
0.42
Multi-Family Home
$1,752,000
11/17/25
4
3.5
1,967
928 Truman Ave #A-D, Key West, FL
0.66
Multi-Family Home
$1,500,000
12/23/25
8
5
1,830
308 Peacon Ln, Key West, FL
0.14
Multi-Family Home
$850,000
10/31/25
3
2.5
1,296

Nearby homes

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Assigned Schools

These are the assigned schools for 314 Simonton St.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Historic Seaport
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Historic Seaport

At least 38 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 90 % Say people would walk alone at night

  • 88 % Say it's walkable to restaurants

  • 84 % Say it's walkable to grocery stores

  • 83 % Say there are sidewalks

  • 79 % Say streets are well-lit

  • 67 % Say yards are well-kept

  • 64 % Say they plan to stay for at least 5 years

  • 62 % Say there's holiday spirit

  • 60 % Say there's wildlife

  • 59 % Say there are community events

  • 57 % Say it's quiet

  • 43 % Say parking is easy

  • 42 % Say neighbors are friendly

  • 35 % Say kids play outside

  • 30 % Say car is needed

Sourced by Trulia users. Learn more about our methodology.
  • Mari.lindsley
    "I've lived here for 2 years and enjoy the walkability to local theatres and restaurants. There's a strong homeless contingency that detracts from the seaport. But you can't blame them for wanting to be in paradise."
    11
    Flag
  • Tom
    "There are many festivals and events that include the Key West Historic Harbor. Venues include Schooner Wharf, Waterfront Brewery, The Marker, etc.."
    2
    Flag
  • Bwruble
    "Tourist don’t clean up after their dogs, but locals do. This is a wonderful neighborhood. Gecko lane is especially beautiful and very private. "
    1
    Flag
  • Ctmortman
    "Perfect place for dogs. There are several dog pearls on the island and some restaurants are pet friendly. I own a dog watching business on Marco Island...a service much needed there"
    2
    Flag
  • Sue S.
    "We vacationed here for the month of February 2014. We did not rent a car but had bikes for a week. We are walkers and walked an average of 1-2 miles for dinner and many miles during the day touring, hiking, etc. This area is accessible to most anything."
    1
    Flag

LGBTQ Local Legal Protections

Team Gardner/Langley, Berkshire Hathaway HomeServices Knight & Gardner Realty
Agent Phone: (305) 902-2447
MLS Internet Data Exchange (IDX) information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the Florida Keys Board of Realtors.
314 Simonton St, Key West, FL 33040 is a 8 bedroom, 11 bathroom, 8,472 sqft multi-family built in 1921. 314 Simonton St is located in Historic Seaport, Key West. This property is currently available for sale and was listed by FLKMLS on Nov 14, 2024. The MLS # for this home is MLS# 612250.