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$3,850,000

  • For Sale
  • Active
  • Townhouse
  • 4 Beds
  • 4 Full Baths
  • 2,691 Sq. Ft.
  • Updated 1 day ago
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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.

Full Property Details for 119 Simonton St

General

  • Price: $3,850,000
  • HOA FEE: $1,650/month
  • Taxes: $20,333 (2025)
  • Status: Active
  • Type: Townhouse
  • Source: 927
  • MLS ID: 619812
  • Updated: 5/18/2026
  • Added to Site: 20 day(s) ago

Interior

  • Interior Features: Entrance Foyer, Walk-in Closet(s), Built-in Cabinets, Elevator, Fire Sprinkler, Granite Counter Top, Wet Bar, Whirlpool Bath Tub
  • Appliances: Stainless Steel Appliance(s), Dishwasher, Dryer, Microwave, Oven, Range, Refrigerator, Washer
  • Flooring: Wood, Tile

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 4

Bedrooms

  • Total Bedrooms: 4

Additional Information

  • Shared Amenities: Pool
  • Pool: Yes
  • Pool Description: Concrete, In Ground
  • Security/Safety: Electric Gate

Exterior

  • Deck/Patio: Roof Top Deck, Open Porch/Balcony
  • Porch/Patio/Deck: Roof Top Deck, Open Porch/Balcony

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Parking Features: Off Street, Covered, Attached

Location

  • Area: 01 - Key West
  • County: Monroe
  • Subdivision: Old Town - Unrecord (1.0)

Community

  • Association: Yes
  • Assoc. Fees Include: Other, Bldg Exterior Mnt, Building Insurance, Common Area Mnt
  • Pets Allowed: Yes

Heating & Cooling

  • Central air: Yes
  • Air Conditioning: Yes
  • Cooling Type: Heat Pump, Central Air, Ceiling Fans(s)

Structural Information

  • Architectural Style: Above Flood, Townhouse
  • Construction Status: Updated/Remodeled
  • Construction: CBS, Combo Construction, Concrete, Stucco
  • Roof: Metal
  • Windows/Doors: Impact Rstnce Doors, Impact Rstnce Window
  • Square Feet: 2,691
  • Sq. Ft. Source: Appraisal
  • Year Built: 2018
  • Property Condition: Updated/Remodeled

Lot Features

  • Property View: Harbor/Marina View, Open Water View, Ocean
  • Lot Size (Acres): 0.03
  • Lot Size (Sq. Ft.): 1,438
  • Lot Size Source: Tax Records
  • Lot Dimensions: 27 x 54
  • Zoning: HRCC - Historic Residential Commercial Core

Water Features

  • Water View: Yes

Financial Considerations

  • Association Fee: Yes
  • Association Fee: $1,650
  • Assoc Fee Freq.: Monthly
  • Tax Amount: $20,333.12
  • Tax Year: 2025
  • Terms: Cash, Conventional

Disclosures and Reports

  • Legal Description: Unit 119 Simonton St - Old Town Villas At Key West Or2721-1202/09 Or2773-709/806(Dec/Cov) Or2951-1078 Or3141-551
  • Flood Zone: AE
  • APN: 00000240-000119

Listed by Brenda Donnelly Real Estate LLC, Brenda J Donnelly (305) 304-1116

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Listing agent

— 119 Simonton St —

  • Brenda J Donnelly

    Brenda Donnelly Real Estate LLC

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 119 Simonton St

School District:Monroe County School District, Middle Torch Key, FL
NameGradesDistance
Horace O'bryant School
1105 Leon Street, Key West, FL 33040
6-81.1 mi
Gerald Adams Elementary School
5855 College Road, Key West, FL 33040
PK-53.9 mi
Key West High School
2100 Flagler Avenue, Key West, FL 33040
9-121.8 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 119 Simonton St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/07/2026
Listed
$3,850,000
79.68%
MLS
2/22/2019
Sold
$2,142,700
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 119 Simonton St

Year
Property Taxes
Change
Tax Assessment
Change
2024
$19,704
—
$2,449,998
3%
2024
$19,704
2%
$2,380,951
3%
2023
$19,408
25%
$2,311,603
34%
2021
$15,497
-17%
$1,720,811
-23%
2022
$18,625
20%
$2,244,275
29%
2021
$15,497
17%
$1,745,910
27%
2019
$13,296
275%
$1,375,308
335%
2018
$3,547
16%
$316,360
10%
2017
$3,048
9%
$287,600
—
2016
$2,795
—
$287,600
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 119 Simonton St

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Brenda Donnelly Real Estate LLC, Brenda J Donnelly (305) 304-1116

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119 Simonton Street, Key West, FL 33040 (MLS# 619812) is a Townhouse property with 4 bedrooms and 4 full bathrooms. 119 Simonton Street is currently listed for $3,850,000 and was received on May 07, 2026. Want to learn more about 119 Simonton Street? Do you have questions about finding other Townhouse real estate for sale in Key West? You can browse all Key West real estate or contact a Coldwell Banker agent to request more information.

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