314 Simonton St, Key West, FL 33040
Property image
Property image
SOLD
JUL 6, 2026

$4,515,100

Trulia Estimate
  • 8 Beds
  • 9 Baths
  • 8,472 sqft

314 Simonton St, Key West, FL 33040

Historic Seaport
Est. Refi. Payment $26,612/mo*
Refinance Your Home
Currently Off Market - Sold Jul 6, 2026 for $4,500,000 (9% below list price)

Home Value

Trulia Estimate
$4.51M
Since last month
Increased$16K (+0.4%)
Since last year
Decreased$2M (-25.5%)
Since last sale
Increased$25K (+0.5%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value decreased by -28% in the last 10 years
MonthEstimated value
2026
August 2026$4.52M
August 2026$4.52M
July 2026$4.51M
2024

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
909 & 913 Thomas St, Key West, FL
0.50
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
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
0.65
Multi-Family Home
$1,500,000
12/23/25
8
5
1,830
1812 Flagler Ave, Key West, FL
1.45
Multi-Family Home
$2,950,000
11/10/25
9
11
8,004

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
320 Simonton St #2, Key West, FL 33040
0.03
$995,400
2
2
1,081
Off Market
526 Rose Ln, Key West, FL 33040
0.02
$2,229,500
2
2
1,320
Off Market
525 Eaton St #NA, Key West, FL 33040
0.05
$3,071,200
Studio
1.5
1
Off Market
331 Simonton St #2, Key West, FL 33040
0.05
$3,270,100
Studio
1.5
2
Off Market
619 Eaton St, Key West, FL 33040
0.08
$1,790,300
3
2.5
2,000
Off Market
616 Caroline St #5, Key West, FL 33040
0.07
$936,000
1
2
754
Off Market
616 Caroline St #6, Key West, FL 33040
0.07
$758,000
1
2
650
Recently Sold
1 Donkey Milk Ln, Key West, FL 33040
0.09
$946,800
2
2
696
Off Market
621 Eaton St, Key West, FL 33040
0.09
$3,286,200
5
5.5
2,448
Off Market
616 Eaton St, Key West, FL 33040
0.11
$7,250,000
5
6
4,000
Recently Sold
322 Elizabeth St, Key West, FL 33040
0.09
$3,145,300
3
3
2,446
Off Market

Local Information

  • Map ViewExplore the area around 314 Simonton St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Multi-Family
Built in 1921
8,472 sqft
$531/sqft

About this House

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.
314 Simonton St, Key West, FL 33040 is a 8 bedroom, 11 bathroom, 8,472 sqft multi-family in Historic Seaport, built in 1921. It last sold for $4,500,000 on Jul 6, 2026 (9% below the $4,950,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $4,515,100, with a rent estimate of $2,956/month.
Last check for updates: about 5 hours ago
Listed by Team Gardner/Langley, (305) 902-2447
Berkshire Hathaway HomeServices Knight & Gardner Realty
Bought with: Berkshire Hathaway HomeServices Knight & Gardner Realty
Source: FLKMLS, MLS#612250

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
View
No View

Exterior Features

Exterior Home Features
Has a Private Pool
Pool
Pool: In Ground, ConcretePool
Frontage
Not on Waterfront

Property Information

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

Price & Status

Price
List Price: $4,950,000Price Per Sqft: $531/sqft

Active Status

MLS Status: Closed

Location

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

Building

Building Area
Building Area: 8472 Square Feet

HOA

HOA Fee Includes: NoneNo HOA

Lot Information

Lot Area: 7840.8 sqft

Miscellaneous

Mls Number: 612250

Price and Tax history

DateEventPrice
Jul 6, 2026
Source: FLKMLS #612250
Sold
$4,500,000
Apr 28, 2026
Source: FLKMLS #612250
Contingent
$4,950,000
Apr 25, 2026
Source: Key West AOR #612250
PriceChange
$4,950,000
Price decreased by 6%
Jan 12, 2026
Source: Key West AOR #612250
PriceChange
$5,250,000
Price decreased by 5%
Jul 28, 2025
Source: FLKMLS #612250
PriceChange
$5,500,000
Price decreased by 7%

Market trends in Key West

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.28M
$50KMoM
Sale-to-List Price
95.1%
0.5%MoM
Price per sq ft
$933
$26MoM
Available listings
271
17MoM

Around this home

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

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 MLS.

Frequently asked questions about 314 Simonton St

  • What is 314 Simonton St estimated to be worth?
    Trulia's estimated value for 314 Simonton St in Key West, FL is $4,515,100.
  • What is the price history for 314 Simonton St?
    314 Simonton St in Key West, FL last sold for $4,500,000 in July 2026.
  • Is Key West a buyer's or seller's market?
    Key West is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Key West?
    The median sale price in Key West is $1.28M. That is up $50K from the prior month.
  • Does 314 Simonton St have a pool?
    Yes, 314 Simonton St in Key West, FL has a pool.

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