NEW 12 HRS AGO

For sale

$2,895,000

Est. $20,397/mo —

•

1,472

sq ft

726 Simonton St, Key West, FL 33040

About this home

Experience the character and charm of historic Old Town Key West at 726 Simonton Street, a distinctive two-story island residence featuring classic architecture, beautiful Dade County pine, and a thoughtfully executed nautical motif that celebrates the island's maritime heritage. Ideally situated in the heart of Old Town, this unique property places Key West's celebrated restaurants, galleries, shopping, entertainment, and waterfront attractions within easy walking or biking distance, while offering the privacy of your own tropical retreat. The first floor features inviting living spaces and a kitchen with French doors opening directly to the lush tropical backyard and private swimming pool. This seamless connection between indoor and outdoor living captures the relaxed island lifestyle that makes Key West so special. Upstairs, an additional living area and second kitchen provide a wonderful extension of the residence, complemented by a covered private deck overlooking Simonton Street. A finished loft, accessed by a traditional ship's ladder, adds another distinctive element to the home's nautical personality and provides additional flexible bonus space. Currently enjoyed as a single-family residence, the property offers interior access between both levels, along with a separate exterior entrance that allows for additional privacy and flexibility. Its Multi-Family Duplex zoning presents an added dimension of versatility for future owners. With its century-old Conch-house architecture, warm Dade County pine interiors, maritime-inspired details, and private tropical pool, 726 Simonton Street is a home that celebrates the history and individuality of Key West.

Single-familyProperty Type

1918Year Built

1,972 sq ftLot Size

$1,967Price/Sq.Ft.

Listed by The Behmke The Behmke Group • Keller Williams Key West Compass Realty

Listing updated: Nov 12, 2026 at 02:13pm

Redfin checked: a minute ago

•Source:FLKMLS #622050

Payment calculator

$20,397 per month

Principal and interest$15,799

Property taxes

$352

HOA dues

Home insurance

$4,246

Utilities

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Open houses

No upcoming open houses.

Nearby open houses (10)

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702 Florida St, Key West, FL 33040
3,386 sq ft lot • Built 1972
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3808 Duck Ave, Key West, FL 33040
6,000 sq ft lot • Pool • Built 1958
OPEN SAT, 11AM TO 1PM3D WALKTHROUGH
$569,000
2 beds1.5 baths1,050 sq ft
3314 Northside Dr #62, Key West, FL 33040
$125 HOA • 2 parking spots • Pool
OPEN SAT, 11AM TO 1PM3D WALKTHROUGH
$2,895,000
3 beds3 baths1,600 sq ft
711 Olivia St, Key West, FL 33040
3,350 sq ft lot • Parking • Pool
OPEN SAT, 12PM TO 1PM
$849,500
3 beds2 baths1,488 sq ft
2928 Fogarty Ave, Key West, FL 33040
6,621 sq ft lot • Built 1963 • Listed 2 days
OPEN SUN, 11AM TO 2PM3D WALKTHROUGH
$2,380,000
4 beds4 baths2,890 sq ft
1701 Ashby St, Key West, FL 33040
5,285 sq ft lot • Pool • Built 1958
OPEN SUN, 1PM TO 3PM3D WALKTHROUGH
$1,505,000
3 beds3 baths1,680 sq ft
1414 18th St, Key West, FL 33040
6,000 sq ft lot • Pool • Built 1965

Around this home

Schools

K - 12
Preschool & daycare

Horace O'bryant School

Public PreK-8 • Assigned • 0.9mi

3/10

Key West High School

Public 9-12 • Assigned • 1.4mi

3/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Living

Interior features
Unfurnished

Bathrooms
2 full bathrooms

Kitchen
Dishwasher, Refrigerator, Range

Laundry & utility
Washer, Dryer

Flooring
Tile, Wood

Heating & cooling
Ductless cooling
Ceiling fans

Sale and tax history for 726 Simonton St

Sale History
Tax History

Date

Event

Price

FLKMLS #622050

Nov 12, 2026

Listed

$2,895,000

$1,967/sq ft

FLKMLS #622051

Nov 12, 2026

Listed

$2,895,000

$1,967/sq ft

+37

FLKMLS #408681

Mar 15, 1999

Sold

$272,500

$185/sq ft

Jan 12, 1998

Listed

$285,000

$194/sq ft

Public Records

Mar 1, 1986

Sold

$65,000

$44/sq ft

Public record

Public record
Zoning
Permits

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

1,904 Sq. Ft.

Year renovated

2012

Finished Sq. Ft.

1,472

Unfinished Sq. Ft.

—

Total Sq. Ft.

1,472

Year built

1918

Style

Multi-Family (2-4 Unit)

County

Monroe County

APN

0668 25 00015800000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Nov 12, 2026.

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

Climate risks

3/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

Heat Factor

We're working on getting current and accurate heat risk information for this home.

10/10 Wind Factor

99% chance of strong winds in next 30 years

1/10 Air Factor

0 unhealthy days expected this year, 0 days in 30 years

Provided by First Street

Historical weather

Key West, FL • 33040

Average low and high temperatures (°F)

73°

65°

76°

67°

79°

71°

81°

75°

86°

81°

88°

82°

89°

83°

90°

81°

87°

80°

85°

78°

80°

73°

77°

69°

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

79/ 100

Good sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

8.1 hrs

6.3 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 726 Simonton St

$2,837,552

$57K under list price of $2.90M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $1.7M to $3.7M.

SOLD APR 7, 2026
$3,050,000 Last sold price
4 beds2.5 baths1,440 sq ft
421 Virginia St, Key West, FL 33040
$151/sq ft
larger lot
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SOLD OCT 23, 2026
$1,995,000 Last sold price
2 beds2.5 baths1,409 sq ft
419 Simonton St Unit c, Key West, FL 33040
$551/sq ft
smaller lot
108 years newer
SOLD MAR 2, 2026
$3,699,000 Last sold price
3 beds3 baths1,663 sq ft
805 Shavers Ln, Key West, FL 33040
$257/sq ft
larger lot
10 years newer
SOLD JUN 17, 2026
$2,895,000 Last sold price
3 beds3.5 baths1,773 sq ft
1315 Newton St, Key West, FL 33040
$334/sq ft
larger lot
108 years newer
SOLD APR 10, 2026
$1,695,000 Last sold price
3 beds3 baths1,553 sq ft
322 Southard St, Key West, FL 33040
$876/sq ft
larger lot
17 years older
SOLD APR 27, 2026
$2,525,000 Last sold price
3 beds3 baths1,600 sq ft
808 Carey Ln, Key West, FL 33040
$389/sq ft
larger lot
10 years newer

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726 Simonton St, Key West, FL 33040

Historic old town • Dade county pine • Nautical motif

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Details provided by FLKMLS and may not match the public record. Learn more.

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About this home

Payment calculator

Affordability tools

See this home in person

Nearby open houses (10)

Around this home

Schools

Lifestyle

Property details

Sale and tax history for 726 Simonton St

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 726 Simonton St

Early Access listings

Nearby similar homes

New listings for sale in 33040

More real estate resources