119 Simonton St

Key West, FL 33040

$3,850,000
Price
4
Beds
2,691 Sq. Ft.
$1,431 / Sq. Ft.
2,691
Sq. Ft.
$1,431
per Sq. Ft.
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Front View
Sunset from rooftop
Back Corner View
Foyer and Elevator
Second Floor Living Room
Fourth Floor Versatile Room
Rooftop Balcony
Entrance Foyer
Second Floor Living Room
Second Floor Living Room
second Floor Living Room
Second Floor Kitchen
Second Floor Kitchen
Second Floor Bedroom
Second Floor Bedroom
Second Floor Bedroom
Second Floor Bathroom
Second Floor Bathroom
Third Floor Bedroom
Third Floor Bedroom
Third Floor Bedroom and Bath
Third Floor Bath
Third Floor Laundry
Third Floor Primary
Third Floor Primary and Bath
Third Floor Primary Bath
Third Floor Primary Bath
Fourth Floor Hallway
Fourth Floor Hallway
Fourth Floor Bath
Fourth Floor Versatile Bonus Room
Fourth Floor Versatile Bonus Room
Fourth Floor Versatile Room
Fourth Floor Wetbar
Rooftop Balcony
Rooftop Balcony
Front View
Conditioned 2 Car Garage
Conditioned 2 Car Garage
Community Pool
Community Pool
119 Simonton Full--3
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Description

Discover modern island luxury at 119 Simonton Street, a premier end-unit townhouse nestled within the exclusive gated community of Old Town Villas. Built in 2018 and spanning a generous 2,691 square feet, this residence seamlessly blends sophisticated contemporary design with the timeless allure of Key West. The interior features new white oak flooring that leads you through an open-concept living space. The kitchen is a true standout, boasting elegant granite countertops and a custom kitchen island--a...Discover modern island luxury at 119 Simonton Street, a premier end-unit townhouse nestled within the exclusive gated community of Old Town Villas. Built in 2018 and spanning a generous 2,691 square feet, this residence seamlessly blends sophisticated contemporary design with the timeless allure of Key West. The interior features new white oak flooring that leads you through an open-concept living space. The kitchen is a true standout, boasting elegant granite countertops and a custom kitchen island--a unique feature in the community. For the ultimate convenience, a private elevator services all four floors of the home, transporting you from the air-conditioned two-car garage to the spectacular rooftop terrace where you can view daily sunrises over the Historic Key West Marina and sunsets over Mallory Square, both a very short walk away. The top floor features a rare full bathroom and a flexible bonus room ideal for a home office or guest suite. Whether you're mixing drinks at the custom wet bar or lounging on the terrace, this level serves as the ultimate private retreat for taking in breathtaking panoramic views. Peace of mind is built into the architecture with full impact-rated windows and doors and a durable metal roof, ensuring the home is as secure as it is beautiful. The third floor has two primary bedrooms featuring large walk-in closets and balconies. The lifestyle offered here is unparalleled, situated just one block off the vibrant energy of Duval Street. You are steps away from the island's best dining and boutiques, yet you can retreat instantly to the quiet security of a gated community. Spend your afternoons lounging by the large tropical community pool and cabana area, enjoying a level of comfort and convenience unsurpassed in the heart of Old Town. With a rare two-car garage and an unbeatable location, this residence captures the very best of the Florida Keys lifestyle.
  1. Listed by Brenda J Donnelly • Brenda Donnelly Real Estate LLC

Property Details for 119 Simonton Street

Waterfront
None
Waterfront
No
Zoning
HRCC - Historic Residential Commercial Core
Subdivision
Old Town - Unrecord (1.0)
Building Style
Townhouse
Vehicle Storage
Garage, Covered Parking, Off Street Parking, Attached
Pets
Pets Allowed
LISTING UPDATED: 06/13/2026 12:55 AM

Property Details for 119 Simonton Street

StatusActive
MLS #619812
Days on Market43
Taxes$20,333 / year
HOA Fees$1,650 / month
Condo/Co-op Fees-
Property TypeTownhouse
MLS TypeResidential / Townhouse
Year Built2018
Lot Size0.03 AC / 1,438 SF
CountyMonroe County
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Location

Listing Courtesy of Brenda Donnelly Real Estate LLC
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Building Information for 119 Simonton Street

Stories4Residences-Year Built2018Lot Size0.03 AC / 1,438 SF

Payment Calculator

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$22,529 per month

30 year fixed, 6.36% Interest

Principal and Interest

$19,185

Property Taxes

$1,694

HOA Dues

$1,650

The Payment Calculator is for illustrative purposes only.

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Property Information for 119 Simonton Street

Summary
Location and General Information
  • Waterview: Ocean View, Harbor/Marina View, Open Water View
  • Area: 01 - Key West
  • Absolute Longitude: 81.804152
  • Control Depth: 0
  • Listing Board: Key West Association
  • Side: Median
  • KW Neighborhood: Old Town-N of Truman
  • Mile Marker: 1.0
  • Marathon Neighborhood: N/A
  • Neighborhood Feature: Community Pool
  • Key/Island: Key West
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: Yes
  • Association Info: 1st Right of Refusal: No
  • Fee Includes: Bldg Exterior Mnt, Other, Common Area Mnt, Building Insurance
  • Furnished: Furnished
  • Tax Year: 2025
  • Tax Exemptions: None
Property
Lot Information
  • Lot Size: 27 X 54
  • Acres: 0.03
  • Parcel #: 00000240-000119
  • Land Size: Less Than 1/4 Acre
Property and Assessments
  • Legal: Unit 119 Simonton St - Old Town Villas At Key West Or2721-1202/09 Or2773-709/806(Dec/Cov) Or2951-1078 Or3141-551
  • MLS Approved: Y
  • SqFt Source: Appraisal
  • Flood Zone: AE
  • Rentals Allowed: With Restrictions
  • Deed Restrictions: Unknown
  • Picture Count: 49
  • Document Count: 0
  • Building Style: Above Flood: Unknown
  • Property Condition: Updated/Remodeled
  • Security: Electric Gate
  • Title: Negotiable
Utilities
  • Utilities: FKAA, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Pool: Yes
  • Pool Info: In Ground, Concrete
  • Porch/Balcony: Open Porch/Balcony, Roof Top Deck
Interior and Exterior Features
Interior Features
  • Floor: Tile, Wood
  • Interior Features: Wet Bar, Whirlpool Bath Tub, Walk-in Closet(s), Fire Sprinkler, Elevator, Granite Counter Top, Built-in Cabinets, Entrance Foyer
  • Pre-Wired: Cable
  • Appliances: Washer, Stainless Steel Appliance(s), Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
Exterior Features
  • Roof: Metal Roof
  • Construction: CBS, Combo Construction, Stucco, Concrete
  • Dockage: None
  • Windows/Doors: Impact Rstnce Window, Impact Rstnce Doors

Property History for 119 Simonton Street

DateEvent & SourcePriceAppreciation
May 7, 2026

Listed (Active)

FKMLS #619812

$3,850,000—
Feb 26, 2019

Sold

FKMLS #584455

$2,100,000—
Feb 26, 2019

Pending

FKMLS #584455

—
DateEvent & SourcePrice
05/07/2026

Listed (Active)

FKMLS #619812

$3,850,000
02/26/2019

Sold

FKMLS #584455

$2,100,000
02/26/2019

Pending

FKMLS #584455

—

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 119 Simonton Street

Taxable ValueLand-Additions-Total-
Tax Record2024$19,704 ($1,642 / month)
Home Facts
Beds3Baths2.5Total Finished SqFt2,400 SqFtAbove Grade Finished SqFt2,400 SqFtStories4Lot Size1,438 SqFtStyleSingle Family ResidenceYear Built2018CountyMONROEAPN00000240-000119

Schools near 119 Simonton Street

This home is within Monroe.
Rating
School
Type
Grades
Distance
Gerald Adams Elementary School
Public - PK to 5
Monroe Virtual Franchise
Public - 6 to 12
Key West High School
Public - 9 to 12
Monroe Virtual Instruction Program (District Provided)
Public - K to 5
Rating
School
Distance
Gerald Adams Elementary School
PublicPK to 5

Monroe Virtual Franchise
Public6 to 12

Key West High School
Public9 to 12

Monroe Virtual Instruction Program (District Provided)
PublicK to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 119 Simonton Street, Key West, FL 33040

119 Simonton Street is a townhouse for sale in Key West, FL 33040. This property was listed for sale on May 7, 2026 by Brenda Donnelly Real Estate LLC, it's currently listed at $3,850,000. It has been on the market for a total of 43 days and was last sold on February 26, 2019. This listing's school district is Monroe. Nearby schools include Gerald Adams Elementary School, Monroe Virtual Franchise and Key West High School. 119 Simonton Street is a 4-bed, 4-bath, 2,691 sqft townhouse built in 2018.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Brenda Donnelly Real Estate LLC

Based on information from one of the following Multiple Listing Services: Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.