NEW 15 HRS AGO

For sale

$3,600,000

Est. $27,431/mo —

•

2,691

sq ft

119 Simonton St, Key West, FL 33040

About this home

Experience modern island luxury at 119 Simonton Street, a premier end-unit townhouse nestled within the secure, private gates of Old Town Villas. Built in 2018 and offering a generous 2,691 square feet of meticulously designed living space, this remarkable residence seamlessly blends sleek contemporary elegance with the timeless charm of historic Key West. Inside, stunning new white oak flooring leads you through a light-filled, open-concept floor plan designed for effortless coastal living. The gourmet kitchen serves as a true center point, featuring premium granite countertops and a custom kitchen island--a distinctive, high-end feature unique within the community. For maximum comfort and accessibility, a private interior elevator services all four levels of the home, transporting you seamlessly from the air-conditioned two-car garage to the ultimate top-floor retreat. The fourth floor is specifically curated for entertaining or quiet relaxation, boasting a custom wet bar, a rare full bathroom, and a flexible bonus room perfect for a home office, secondary lounge, or private guest suite. Step out onto the expansive rooftop terrace to take in panoramic island views, featuring beautiful daily sunrises over the Historic Key West Marina and colorful sunsets over Mallory Square. The third floor hosts two spacious primary bedroom suites, each complete with generous walk-in closets, luxurious ensuite baths, and private balconies overlooking the lush grounds. Built for complete peace of mind, the townhouse is constructed with full impact-rated windows and doors alongside a durable metal roof. Residents enjoy exclusive access to a tropical community pool and cabana area, all located just one block from the vibrant energy, fine dining, and boutique shopping of Duval Street. With its rare two-car garage and uncompromised location, this home delivers an exceptional Key West sanctuary.

TownhomeProperty Type

2018Year Built

1,438 sq ftLot Size

$1,338Price/Sq.Ft.

$1,650/moHOA Dues

2 spacesParking

Listed by Brenda Donnelly • Brenda Donnelly Real Estate LLC

Listed by Callie Harris • Brenda Donnelly Real Estate LLC

Listing updated: Nov 10, 2026 at 03:19pm

Redfin checked: a minute ago

•Source:FLKMLS #622016

Payment calculator

$27,431 per month

Principal and interest$19,647

Property taxes

HOA dues

Home insurance

Utilities

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Open houses

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Around this home

Schools

K - 12
Preschool & daycare

Horace O'bryant School

Public PreK-8 • Assigned • 1.1mi

3/10

Key West High School

Public 9-12 • Assigned • 1.8mi

3/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Market insights

119 Simonton St · $3,600,000

DAYS ON MARKET

The average home goes pending in 248 days.

SALE-TO-LIST

Most homes are selling 7% below list price.

LIST PRICE

Median sale price in this area is $898,208. (75% lower than this home)

PRICE DROP

13% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Wet bar
Entrance foyer
Elevator
Walk-in closet
Built-in features
Granite counters
Furnished

Bathrooms
4 full bathrooms

Kitchen
Dishwasher
Refrigerator
Range
Oven
Microwave

Laundry & utility
Washer
Dryer

Flooring
Tile
Wood

Heating & cooling
Central heating
Central air
Heat pump
Ceiling fans

Sale and tax history for 119 Simonton St

Sale History
Tax History

Date

Event

Price

FLKMLS #622016

Nov 9, 2026

Listed

$3,600,000

$1,338/sq ft

FLKMLS #620913

Nov 8, 2026

Listing Removed

—

Aug 8, 2026

Listed

$3,600,000

$1,338/sq ft

FLKMLS #619812

Aug 8, 2026

Listing Removed

—

Jul 23, 2026

Price Changed

$3,600,000

$1,338/sq ft

May 7, 2026

Listed

$3,850,000

$1,431/sq ft

Public Records

Mar 1, 2019

Sold

$2,142,700

$796/sq ft

FLKMLS #584455

Feb 26, 2019

Sold

$2,100,000

$780/sq ft

Feb 26, 2019

Listed

$2,100,000

$780/sq ft

Public Records

Jan 22, 2015

Sold

$6,800,000

$2,527/sq ft

Public Records

May 13, 2003

Sold

$4,350,100

$1,617/sq ft

Public record

Public record
Zoning
Permits

Beds

Baths

2.5

Stories

Lot width

—

Lot depth

—

Lot size

1,458 Sq. Ft.

Year renovated

2018

Finished Sq. Ft.

2,400

Unfinished Sq. Ft.

—

Total Sq. Ft.

2,400

Year built

2018

Style

Townhouse

County

Monroe County

APN

0668 25 00000240000119

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Nov 10, 2026.

HRCC-1

Historic Residential Commercial Core, Duval Street Gulfside District

The HRCC-1 Duval Street gulfside district incorporates the city's intensely vibrant tourist commercial entertainment center which is characterized by specialty shops, sidewalk-oriented restaurants, lounges and bars with inviting live entertainment; and transient residential accommodations. The core of the commercial entertainment center spans generally from the Pier House south to Petronia Street as specifically referenced on the official zoning map. This segment of Duval Street is the most intense activity center in the historic commercial core. The following light manufacturing and warehousing uses are located within the eastern portion of the HRCC-1 district: Strunk Lumber Yard.; Key West Aloe Processing Plant.; Key West Hand Print Fabric Shop.; These light manufacturing and warehouse uses include real estate parcel numbers 24, 29, 36, 99, and 116, as delineated in the county property appraiser's city property location map dated January, 1991. In addition to uses generally allowed throughout the HRCC-1 area, the following light industrial and warehouse uses may locate exclusively within these areas i.e., real estate parcels 24, 29, 36, 99, and 116 upon satisfying comprehensive performance criteria, including but not limited to nuisance abatement standards, screening and buffering, concurrency management, open space, and all such activities must be under roof with no open yard storage: Warehousing and wholesaling within enclosed buildings; Service and repair establishments, excluding vehicle and heavy machinery service and repair; business services; printing shops; and similar uses; Light manufacturing, excluding metal processing or fabrication, including light processing, assembly and distribution functions, electronics, research and development, and similar uses; Building materials supply and storage, and contractor's storage; Vocational trade schools; Enclosed parking facilities; and Accessory uses.

Permitted uses

Include but are not limited to:

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

Climate risks

9/10 Flood Factor

Estimated 80%+ chance 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)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

92/ 100

Exceptional sunlight

Sunscore

This home ranks in the top 28% for direct sun exposure in Key West. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9 hrs

6.7 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 119 Simonton St

$3,577,949

$22K under list price of $3.60M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $2.9M to $4.3M.

SOLD MAR 18, 2026
$3,285,000 Last sold price
4 beds3 baths1,852 sq ft
418 William St, Key West, FL 33040
$436/sq ft
larger lot
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SOLD JUN 17, 2026
$2,895,000 Last sold price
3 beds3.5 baths1,773 sq ft
1315 Newton St, Key West, FL 33040
$295/sq ft
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SOLD MAY 28, 2026
$4,250,000 Last sold price
3 beds3.5 baths2,833 sq ft
1320 Grinnell St, Key West, FL 33040
$162/sq ft
larger lot
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SOLD MAR 2, 2026
$3,699,000 Last sold price
3 beds3 baths1,663 sq ft
805 Shavers Ln, Key West, FL 33040
$886/sq ft
larger lot
90 years older
SOLD MAY 21, 2026
$3,875,000 Last sold price
5 beds4 baths2,619 sq ft
905 Von Phister St, Key West, FL 33040
$142/sq ft
larger lot
55 years older
SOLD APR 7, 2026
$3,050,000 Last sold price
4 beds2.5 baths1,440 sq ft
421 Virginia St, Key West, FL 33040
$780/sq ft
larger lot
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Rental earnings

Est. $6,223 per month, based on comparable rentals

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