Lindsay Ryan
EXP Realty LLC
(786) 751-4493
64 Total Sales
5 in Old Town
$840K - $4.8M Price Range
419 Simonton St Unit A Key West, FL 33040
Old Town Neighborhood
2
Beds
2.5
Baths
1,082
Sq Ft
1,704
Sq Ft Lot
Highlights
- Furnished
- Impact Glass
- Central Air
- Wood Frame Window
- Walk-In Closet
- Ceiling Fan
About This Home
As of May 2026The 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.
Last Buyer's Agent
Thomas Mack
SBX Real Estate, LLC (KW)
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Property Details
Home Type
- Condominium
Est. Annual Taxes
- $13,468
Year Built
- Built in 1889
Lot Details
- Privacy Fence
Home Design
- Frame Construction
- Metal Roof
Interior Spaces
- 1,082 Sq Ft Home
- 2-Story Property
- Furnished
- Ceiling Fan
- Drapes & Rods
- Wood Frame Window
Kitchen
- Oven
- Microwave
- Freezer
- Dishwasher
- Wine Cooler
- Built-In or Custom Kitchen Cabinets
- Disposal
Bedrooms and Bathrooms
- 2 Bedrooms
- Walk-In Closet
Laundry
- Dryer
- Washer
Home Security
Utilities
- Central Air
- Separate Meters
Listing and Financial Details
- Assessor Parcel Number 00006340-000000
Community Details
Overview
- Old Town Unlisted Subdivision
Pet Policy
- Pets Allowed
Security
- Impact Glass
- Fire and Smoke Detector
Home Values in the Area
Average Home Value in this Area
Agents Specializing in Old Town, FL
-
Lindsay Ryan
-
Anneliese Dietrick
Anneliese Dietrick
Coldwell Banker Schmitt Lower Keys (KW)
(844) 666-4591
37 Total Sales
3 in Old Town
$1.1M - $2.9M Price Range
-
Mike Kane
Mike Kane
Internet Realty of the Florida Keys
(703) 884-2537
25 Total Sales
5 in Old Town
$750K - $910K Price Range
-
Austin Kimbler
Austin Kimbler
Expert Realty LLC (HQ)
(786) 901-8149
49 Total Sales
7 in Old Town
$850K - $3.7M Price Range
-
Emily Lombard
Emily Lombard
Ocean Sotheby's International Realty
(833) 447-1049
41 Total Sales
14 in Old Town
$550K - $3.4M Price Range
-
Sandra Tuttle
Sandra Tuttle
Island Welcome Real Estate
(786) 751-6441
138 Total Sales
4 in Old Town
$1,520,000 Price Range
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 05/22/2026 05/22/26 | Sold | $1,325,000 | -3.6% | $1,225 / Sq Ft |
| 03/11/2026 03/11/26 | Price Changed | $1,375,000 | -7.4% | $1,271 / Sq Ft |
| 01/22/2026 01/22/26 | For Sale | $1,485,000 | -- | $1,372 / Sq Ft |
Source: Key West Association of REALTORS®
Agents Affiliated with this Home
-
Team Kaufelt
Seller's Agent in 2026
Team Kaufelt
Truman & Co. (KW)
(305) 393-1267
55 in this area
127 Total Sales
-
T
Buyer's Agent in 2026
Thomas Mack
SBX Real Estate, LLC (KW)
-
T
Buyer's Agent in 2026
Tommy Mack
Buy The Keys (KW)
Map
Source: Key West Association of REALTORS®
MLS Number: 618250
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
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