SOLD JUL 6, 2026

Sold on jul 2026

$4,500,000

•

8,472

sq ft

314 Simonton St, Key West, FL 33040

Track this home’s value and nearby sales activity

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.

Multi-familyProperty Type

1921Year Built

7,750 sq ftLot Size

$531Price/Sq.Ft.

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

Bought with Zainya Zimmerer • Berkshire Hathaway HomeServices Knight & Gardner Realty

Redfin checked: a minute ago

•Source:FLKMLS #612250

Redfin Estimate

Unfortunately, we don't have enough data to generate an accurate Estimate at this time.

Market trends in 33040, FL

Last updated October 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-list price

94.4%

1.2% MoM

Median sale price

$1,000K

$294 MoM

Avg. days on market

135d

5 days MoM

Recently sold homes

111

3 MoM

New listings for sale

NEW 27 HRS AGO
$5,300,000
7 beds6 baths3,121 sq ft
923 Fleming St, Key West, FL 33040
3D WALKTHROUGH
$2,199,000
3 beds2 baths1,704 sq ft
3821 Eagle Ave, Key West, FL 33040
$2,249,000
4 beds3.5 baths1,703 sq ft
1104 Packer St, Key West, FL 33040
$895,000
3 beds2 baths810 sq ft
1004 Watson St #1, Key West, FL 33040
3D WALKTHROUGH
$979,000
3 beds2 baths1,324 sq ft
1709 Catherine St, Key West, FL 33040
$779,000
3 beds2 baths1,152 sq ft
511 Avenue D Unit B, Key West, FL 33040
$2,099,000
5 beds4 baths1,201 sq ft
1125 Angela St, Key West, FL 33040
3D WALKTHROUGH
$1,895,000
8 beds4 baths3,383 sq ft
905 Grinnell St, Key West, FL 33040
$2,190,000
5 beds4 baths2,366 sq ft
1519 Johnson St, Key West, FL 33040
3D WALKTHROUGH
$1,395,000
4 beds2 baths1,743 sq ft
34 Key Haven Rd, Key West, FL 33040
See all

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Sale and tax history for 314 Simonton St

Sale History
Tax History

Date

Event

Price

FLKMLS #612250

Jul 6, 2026

Sold

$4,500,000

$531/sq ft

Apr 28, 2026

Contingent

—

Apr 25, 2026

Price Changed

$4,950,000

$584/sq ft

Apr 8, 2026

Price Changed

$5,250,000

$620/sq ft

Apr 8, 2026

Price Changed

$5,100,000

$602/sq ft

Jan 12, 2026

Price Changed

$5,250,000

$620/sq ft

Jul 28, 2025

Price Changed

$5,500,000

$649/sq ft

May 20, 2025

Price Changed

$5,900,000

$696/sq ft

Apr 1, 2025

Price Changed

$6,400,000

$755/sq ft

Nov 14, 2024

Listed

$6,900,000

$814/sq ft

Public record

Public record
Zoning
Permits

Beds

—

Baths

—

Stories

Lot width

—

Lot depth

—

Lot size

7,750 Sq. Ft.

Year renovated

1998

Sq. Ft.

5,343

Year built

1921

Style

Single Family Residential

County

Monroe County

APN

00004210000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Nov 14, 2024.

HNC-1

Historic Neighborhood Commercial District- Truman/Simonton

The historic neighborhood commercial district Truman/Simonton HNC-1 consists of Simonton, Truman Avenue, and White Street South Corridors. The HNC-1 district is located along major segments of Simonton Street, from Caroline South to United Street; Truman Avenue, from Simonton Street northeast to White Street; and White Street, from Truman Avenue south to United Street; and generally includes larger scale commercial uses oriented toward the motoring public.

Permitted uses

Include but are not limited to:

Religious facility
Commercial & retail
Hospital / medical center
Housing-Group
Housing-Single unit
Housing-Multiple units
Hotel / motel
Office
Veterinary clinic
Park & open space

Property details

Interior

Interior Features
Windows/Doors: Sliding Glass Doors
Appliances: Other: YES

Bathroom Information
# of Full Baths: 7
# of Half Baths: 4

Exterior

Boat Slip/Dock Information
Dockage: None

Exterior Features
Has Pool
Pool Information: In Ground, Concrete

Property Features
Waterfront Type: None
Waterview: No Waterview

Property Information
Deed Restrictions: Unknown
Pets: Pets Allowed
Rentals Allowed: With Restrictions
Min Rental Days: 30

Lot Information
Acres: 0.18
Zoning: HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med
Land Size: Less Than 1/4 Acre
Flood Zone: 0.2 PCT ANNUAL CHANC

Building Information
Year Built: 1,921
Sq. Ft. Source: Property Data Card
Building Style: Other Bldg Style
Building Style: Stories: 3
Building Style: Above Flood: Unknown
Construction: Combo Construction
Roof: Metal Roof

Subdivision/Neighborhood
Subdivision: Old Town - Unlisted (1.0)
Key West Neighborhood: Old Town-N of Truman
Marathon Neighborhood: N/A

Financial

Tax Information
Taxes: $13,667.88
Tax Year: 2,023
Tax Exemptions: None

Utilities

Utility Information
Utilities: FKAA, Municipal Sewer
Has Public Sewer Hook-up

Location

Multi-Unit Information
# of Total Units: 8

Homeowners Association Information
Association Info: 1st Right of Refusal: No
Association Info: Association Fee $: 0.00
Fee Includes: None

Location Information
Side: Median
Mile Marker: 1.00

Public facts

Beds: —
Baths: —
Sq. Ft.: 5,343
Stories: 1.0
Lot Size: 7,750 square feet
Style: Single Family Residential
Year Built: 1921
Year Renovated: 1998
County: Monroe County
APN: 00004210000000

Home facts updated by county records on Nov 14, 2024

Around this home

Schools

Horace O'bryant School

Public PreK-8 • Assigned • 1.1mi

3/10

Key West High School

Public 9-12 • Assigned • 1.7mi

3/10

Provided by GreatSchools

Historical weather

Key West, FL • 33040

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

85/ 100

Very good sunlight

Sunscore

This home receives average direct sun exposure in Key West. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.1 hrs

6.7 hrs

JuneDecember

Provided by Shadowmap

Sell confidently with a local market expert in Key West.

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New listings for sale in 33040

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Outdoor shower • 4,525 sq ft lot • Pool

3D WALKTHROUGH

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Private courtyard • 29x15 pool • Shaded terrace

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Grand foyer • Tall ceilings • Hardwood floors

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Historic charm • New plumbing • New electric wiring

3D WALKTHROUGH

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3 beds2 baths1,324 sq ft

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Large lot • Fenced rear yard • 6,826 sq ft lot

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3D WALKTHROUGH

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Off-street parking • Separate entrances • Outdoor spaces

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Bocce courts • Local dog park • 5,280 sq ft lot

Home values near 314 Simonton St

Data from public records.

Address	Redfin Estimate
328 Simonton Street, Key West, FL 3 Beds \| 2 Baths \| 2920 Sq. Ft.	—
331 Simonton Street, Key West, FL 4 Beds \| 3 Baths \| 2249 Sq. Ft.	$1,757,994

Address	Redfin Estimate
220 Simonton Street, Key West, FL 3 Beds \| 2 Baths \| 1500 Sq. Ft.	—
218 Simonton Street, Key West, FL 5 Beds \| 5.5 Baths \| 2812 Sq. Ft.	$4,001,769

Address	Redfin Estimate
400 Simonton Street, Key West, FL 8 Beds \| 9 Baths \| 4078 Sq. Ft.	$3,941,646
320 Simonton Street Unit Cottage 2, Key West, FL 2 Beds \| 2 Baths \| 1081 Sq. Ft.	$918,394

Property information provided by FLKMLS when last listed in 2024. This data may not match . Learn more.

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314 Simonton St, Key West, FL 33040

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About this home

Redfin Estimate

Market trends in 33040, FL

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Sale and tax history for 314 Simonton St

Public record

Property details

Interior

Exterior

Financial

Utilities

Location

Public facts

Around this home

Schools

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 33040

Home values near 314 Simonton St

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