119 Simonton St, Key West, FL 33040
FOR SALE

119 Simonton St
Key West, FL 33040

Historic Seaport
  • 4 Beds
  • 4 Baths
  • 2,691 sqft

$3,850,000

Est. Mortgage $23,340/mo*
Get Pre-Qualified

$3,850,000

Est. Mortgage $23,340/mo*
Get Pre-Qualified
4 Beds
4 Baths
2,691 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

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 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.

Home Highlights

Parking
Attached Garage
Outdoor
Porch, Deck, Pool
View
Ocean, Harbor/Marina View, Water
HOA
$1,650/Monthly
Price/Sqft
$1,431
Listed
43 days ago

Home Details for 119 Simonton St

Interior Features

Interior Details
Wet Bar
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 4
Dimensions and Layout
Living Area: 2691 Square Feet
Appliances & Utilities
Utilities: FKAA, Cable ConnectedAppliances: Washer, Stainless Steel Appliance(s), Microwave, Oven, Range, Refrigerator, Dishwasher, DryerDishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Has CoolingAir Conditioning: Central Air,Ceiling Fans(s),Heat Pump
Windows, Doors, Floors & Walls
Window: Impact Rstnce WindowDoor: Impact Rstnce DoorsFlooring: Tile, Wood
Levels, Entrance, & Accessibility
Stories: 4Levels: 4 StoriesElevatorFloors: Tile, Wood
View
Has a ViewView: Ocean, Harbor/Marina View, Water
Security
Security: Fire Sprinkler System, Electric Gate
Room & Shared Space
Shared space is furnished

Exterior Features

Exterior Home Features
Roof: MetalPatio / Porch: Open Porch/Balcony, Roof Top DeckHas a Private Pool
Parking & Garage
No CarportHas a GarageHas an Attached GarageNo Open ParkingParking Spaces: 2Parking: Garage,Covered,Off Street,Attached
Pool
Pool: In Ground, ConcretePool
Frontage
Waterfront: None, Dockage: NoneNot on Waterfront
Water & Sewer
Sewer: Municipal Sewer, Public Sewer

Days on Market

Days on Market: 43

Property Information

Year Built
Year Built: 2018
Property Type / Style
Property Type: ResidentialProperty Subtype: Townhouse, Residential - Condo/TownhouseArchitecture: Townhouse
Building
Construction Materials: CBS, Combo Construction, Stucco, ConcreteNot a New Construction
Property Information
Condition: Updated/RemodeledParcel Number: 00000240000119

Price & Status

Price
List Price: $3,850,000Price Per Sqft: $1,431

Active Status

MLS Status: Active

Location

Direction & Address
City: Key WestCommunity: Old Town - Unrecord (1.0)

Agent Information

Listing Agent
Listing ID: 619812

Community

Community Features: Pool

HOA

HOA Fee Includes: Maintenance Structure, Other, Maintenance Grounds, Building InsuranceAssociation for this Listing: Key West AssociationHas an HOAHOA Fee: $1,650/Monthly

Lot Information

Lot Area: 1306.8 sqft

Listing Info

Special Conditions: Standard

Offer

Listing Terms: Cash, Conventional

Rental Terms, Policies & Fees

Furnished

Miscellaneous

Mls Number: 619812Water ViewWater View: Ocean, Harbor/Marina View, Water

Additional Information

Pool
Last check for updates: about 5 hours ago
Listing courtesy of Brenda J Donnelly, (305) 304-1116
Brenda Donnelly Real Estate LLC
Originating MLS: Key West Association
Source: FLKMLS, MLS#619812
Also Listed on FLKMLS, Key West AOR, Key West AOR.

Market trends in Key West

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.2M
$61.67KMoM
Sale-to-List Price
94.9%
0.4%MoM
Price per sq ft
$940
$14MoM
Available listings
304
28MoM

Price History for 119 Simonton St

DatePriceEventSource
05/07/2026$3,850,000Listed For SaleFLKMLS #619812
02/26/2019$2,100,000Sold
FLKMLS #584455

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Property Tax and Assessment

Year2025
Tax$20,333
Assessment$3,171,731
Home facts updated by county records

Comparable Sales for 119 Simonton St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
129 Simonton St, Key West, FL
0.02
Townhouse
$3,300,000
08/28/25
4
4
2,697
149 Simonton St, Key West, FL
0.04
Townhouse
$2,900,000
08/01/25
3
3.5
2,697
506 Emma St, Key West, FL
0.50
Townhouse
$2,362,000
04/14/26
3
3
1,608
101 Front St #8, Key West, FL
0.42
Townhouse
$1,345,000
05/20/26
2
2.5
1,216
101 Front St #15, Key West, FL
0.41
Townhouse
$1,220,000
09/30/25
2
2.5
1,216
208 Fleming St, Key West, FL
0.45
Townhouse
$1,070,000
03/02/26
2
2.5
960
528 Porter Ln, Key West, FL
0.50
Townhouse
$1,245,000
04/01/26
2
2.5
960
548 Porter Ln, Key West, FL
0.49
Townhouse
$1,160,000
01/16/26
2
2.5
960
212 Southard St, Key West, FL
0.53
Townhouse
$1,050,000
05/01/26
2
2.5
960

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Assigned Schools

These are the assigned schools for 119 Simonton St.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Historic Seaport
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Historic Seaport

At least 38 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 90 % Say people would walk alone at night

  • 88 % Say it's walkable to restaurants

  • 84 % Say it's walkable to grocery stores

  • 83 % Say there are sidewalks

  • 79 % Say streets are well-lit

  • 67 % Say yards are well-kept

  • 64 % Say they plan to stay for at least 5 years

  • 62 % Say there's holiday spirit

  • 60 % Say there's wildlife

  • 59 % Say there are community events

  • 57 % Say it's quiet

  • 43 % Say parking is easy

  • 42 % Say neighbors are friendly

  • 35 % Say kids play outside

  • 30 % Say car is needed

Sourced by Trulia users. Learn more about our methodology.
  • Mari.lindsley
    "I've lived here for 2 years and enjoy the walkability to local theatres and restaurants. There's a strong homeless contingency that detracts from the seaport. But you can't blame them for wanting to be in paradise."
    11
    Flag
  • Tom
    "There are many festivals and events that include the Key West Historic Harbor. Venues include Schooner Wharf, Waterfront Brewery, The Marker, etc.."
    2
    Flag
  • Bwruble
    "Tourist don’t clean up after their dogs, but locals do. This is a wonderful neighborhood. Gecko lane is especially beautiful and very private. "
    1
    Flag
  • Ctmortman
    "Perfect place for dogs. There are several dog pearls on the island and some restaurants are pet friendly. I own a dog watching business on Marco Island...a service much needed there"
    2
    Flag
  • Sue S.
    "We vacationed here for the month of February 2014. We did not rent a car but had bikes for a week. We are walkers and walked an average of 1-2 miles for dinner and many miles during the day touring, hiking, etc. This area is accessible to most anything."
    1
    Flag

LGBTQ Local Legal Protections

Brenda J Donnelly, Brenda Donnelly Real Estate LLC
Agent Phone: (305) 304-1116
MLS Internet Data Exchange (IDX) information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the Florida Keys Board of Realtors.
119 Simonton St, Key West, FL 33040 is a 4 bedroom, 4 bathroom, 2,691 sqft townhouse built in 2018. 119 Simonton St is located in Historic Seaport, Key West. This property is currently available for sale and was listed by FLKMLS on May 7, 2026. The MLS # for this home is MLS# 619812.