419 Simonton Street A 618250
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.
| Price: | $1325000 |
|---|---|
| Address: | 419 Simonton Street A |
| City: | Key West |
| State: | Florida |
| Zip Code: | 33040 |
| Subdivision: | Old Town - Unlisted (1.0) |
| MLS: | 618250 |
| Year Built: | 1889 |
| Square Feet: | 1,082 |
| Bedrooms: | 2 |
| Bathrooms: | 3 |
| Half Bathrooms: | 1 |
| roof2: | Metal Roof |
|---|---|
| cooling: | Central Air, Ceiling Fans(s) |
| dockage: | None |
| taxYear: | 2025 |
| flooring: | Wood |
| landSize: | Less Than 1/4 Acre |
| shutters: | Other |
| coolingYN: | yes |
| furnished: | Furnished |
| mlsStatus: | Closed |
| utilities: | Water Separate Meter, Elect Separate Meter |
| waterview: | No Waterview |
| appliances: | Washer, Dryer, Dishwasher, Refrigerator, Oven, Microwave, Disposal, Freezer, Wine Cooler |
| postalCity: | KEY WEST |
| utilities2: | FKAA, Municipal Sewer, Buyer to Verify, Water Separate Meter, Elect Separate Meter |
| waterfront: | None |
| lotSizeArea: | 1704 |
| petsAllowed: | Yes |
| listingTerms: | Cash, Conventional |
| lotSizeUnits: | Square Feet |
| mlsAreaMajor: | 02 - Key West |
| mlsAreaMinor: | 02 - Key West |
| waterfrontYN: | no |
| windowsDoors: | Wood Windows, Impact Rstnce Window, Impact Rstnce Doors |
| associationYN: | yes |
| poolPrivateYN: | no |
| associationFee: | 1343.68 |
| taxAnnualAmount: | 13468.4 |
| exteriorFeatures: | Privacy Wall/Fence |
| interiorFeatures: | Built-in Cabinets, Walk-in Closet(s) |
| communityFeatures: | Fire Hydrant, Beach, Bike Paths |
| interiorFeatures2: | Drapes/Blinds Incl, Built-in Cabinets, Smoke Alarms, Walk-in Closet(s), Window Treatments |
| lotSizeSquareFeet: | 1704 |
| architecturalStyle: | Conch |
| buildingAreaSource: | Seller |
| bathroomsTotalDecimal: | 2.5 |
| constructionMaterials: | Frame |
| patioAndPorchFeatures: | Open Porch/Balcony |
| associationFeeIncludes: | Common Area Mnt |
| financialStatusBankOwned: | No |
| contractInformationBankOwned: | No |
| locationTaxLegalKwNeighborhood: | Old Town-N of Truman |
| associationInfo1stRightOfRefusal: | Yes |
| financialStatusPotentialShortSale: | No |
| locationTaxLegalMarathonNeighborhood: | N/A |
| contractInformationPotentialShortSale: | No |
©2026 Florida Keys MLS, Inc. The data relating to real estate for sale on this web site comes in part from the Florida Keys Multiple Listing Service. The information being provided is 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. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Information is deemed reliable but not guaranteed. Data last updated: Saturday, May 23rd, 2026 at 03:07:25 AM.
Data services provided by IDX Broker
Listed by: Truman & Co. (KW) 305-292-2244
