419 Simonton St #A, Key West, FL 33040
Property image
Property image
SOLD
MAY 22, 2026

419 Simonton St #A
Key West, FL 33040

Historic Seaport
  • 2 Beds
  • 2.5 Baths
  • 1,082 sqft

$1,325,000

Last Sold: May 22, 2026
4% below list $1.38M
$1,225/sqft
Est. Refi. Payment $7,645/mo*
Refinance Your Home

$1,325,000

Last Sold: May 22, 2026
4% below list $1.38M
$1,225/sqft
Est. Refi. Payment $7,645/mo*
Refinance Your Home
2 Beds
2.5 Baths
1,082 sqft

Local Information

  • Map ViewExplore the area around 419 Simonton St #A.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Description

The rare kind of antiquity that comes with all the comforts of today. Built before 1889 and reimagined for modern living, 419 Simonton Street A captures the true spirit of Old Town Key West--authentic, refined, and timeless. Once a mixed-use landmark with a flower shop below and a residence above, the home has been meticulously restored and reimagined from the ground up, with construction completed in January 2026 and every system, surface, and finish entirely new. Offered fully furnished with a bespoke interiors program by Ben Teague Design, the residence is layered with thoughtful selections, timeless materials, and a quiet sophistication that feels both intentional and effortlessly livable. The home offers two bedrooms and two-and-a-half baths, including an upstairs primary bedroom that opens to a classic Key West porch, while a second porch downstairs extends the living space and reinforces the home's effortless indoor-outdoor rhythm. Architect-led design and professionally curated landscaping elevate the curb appeal to a truly top-tier example of Old Town style--timeless proportions, thoughtful detailing, and a presence that feels historic without feeling precious. The property is part of a thoughtfully structured HOA, which also includes one attached residential unit positioned to the rear of the main home, as well as a separate detached unit located at the back of the property--allowing for shared stewardship while preserving privacy and architectural integrity. Set on one of the highest elevation blocks in Old Town and located in the coveted X-500 flood zone, this is a rare opportunity to own a home where heritage, design integrity, and modern peace of mind converge on one of Key West's most iconic streets.
419 Simonton St #A, Key West, FL 33040 is a 2 bedroom, 3 bathroom, 1,082 sqft condo in Historic Seaport, built in 1889. It last sold for $1,325,000 on May 22, 2026 (4% below the $1,375,000 asking price). It is currently off market. The Trulia Estimate is $1,324,800, with a rent estimate of $5,538/month.

Home Highlights

Parking
No Info
Outdoor
Porch
View
No Info
HOA
None
Price/Sqft
$1,225/sqft
Listed
177 days ago

Home Details for 419 Simonton St #A

Interior Features

Beds & Baths
Number of Bedrooms: 2Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 1082 Square Feet
Appliances & Utilities
Utilities: FKAA, Buyer to VerifyAppliances: Washer, Wine Cooler, Freezer, Disposal, Microwave, Oven, Refrigerator, Dishwasher, DryerDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Has CoolingAir Conditioning: Central Air,Ceiling Fans(s)
Gas & Electric
Electric: Elect Separate Meter
Windows, Doors, Floors & Walls
Window: Drapes/Blinds Incl, Window Treatments, Wood Frames, Impact Rstnce Window, OtherDoor: Impact Rstnce DoorsFlooring: Wood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Wood
Security
Security: Smoke Detector(s)
Room & Shared Space
Shared space is furnished

Exterior Features

Exterior Home Features
Roof: MetalPatio / Porch: Open Porch/BalconyFencing: PrivacyNo Private Pool
Frontage
Waterfront: None, Dockage: NoneNot on Waterfront
Water & Sewer
Sewer: Municipal Sewer, Public Sewer

Property Information

Year Built
Year Built: 1889
Property Type / Style
Property Type: ResidentialProperty Subtype: Condominium, Multi FamilyArchitecture: Conch
Building
Construction Materials: Frame
Property Information
Parcel Number: 00006340000000

Price & Status

Price
List Price: $1,375,000Price Per Sqft: $1,225/sqft

Active Status

MLS Status: Closed

Media

Location

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

Community

Community Features: Fire Hydrant, Bike Paths, Beach

HOA

HOA Fee Includes: Maintenance GroundsAssociation for this Listing: Key West AssociationHas an HOA

Lot Information

Lot Area: 1704 sqft

Offer

Listing Terms: Cash, Conventional

Rental Terms, Policies & Fees

Furnished

Miscellaneous

Mls Number: 618250Water View: None

Additional Information

Fire HydrantBike PathsBeach
Last check for updates: about 10 hours ago
Listed by Team Kaufelt, (305) 393-1267
Truman & Co. (KW)
Bought with: Tommy Mack, (305) 731-7910, Coastal Collection Real Estate Inc.
Originating MLS: Key West Association
Source: FLKMLS, MLS#618250

Price History for 419 Simonton St #A

DatePriceEventSource
05/22/2026$1,325,000Sold
FLKMLS #618250
03/27/2026$1,375,000ContingentKey West AOR #618250
03/11/2026$1,375,000PriceChange
FLKMLS #618250
01/22/2026$1,485,000Listed For SaleKey West AOR #618250

Market trends in Key West

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.23M
$20.83KMoM
Sale-to-List Price
94.6%
0.3%MoM
Price per sq ft
$958
$15MoM
Available listings
288
17MoM
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Comparable Sales for 419 Simonton St #A

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
404 Porter Ln #16, Key West, FL
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1,034
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115 Front St #102, Key West, FL
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115 Front St #301, Key West, FL
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2
2
1,250
107 Front St #215, Key West, FL
0.38
Condo
$2,035,000
12/29/25
2
2.5
1,350

Nearby homes

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Assigned Schools

These are the assigned schools for 419 Simonton St #A.
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

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Homes for sale near 419 Simonton St #A

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Off Market Homes Near 419 Simonton St #A

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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.