419 Simonton Street A, Key West, FL 33040
$1,375,000
Property Type:
Residential
Bedrooms:
2
Baths:
3
Square Footage:
1,082
Lot Size (sq. ft.):
1,704
Status:
Contingent/Show
Current Price:
$1,375,000
List Date:
1/22/2026
Last Modified:
4/13/2026
Listing Details MLS# 618250
Location, Tax & Legal
- Street #
- 419
- Street Name
- Simonton
- Street Suffix
- Street
- Key/Island
- Key West
- State/Province
- FL
- Zip Code
- 33040
- County
- Monroe
- Subdivision
- Old Town - Unlisted (1.0)
- Area
- 02 - Key West
- KW Neighborhood
- Old Town-N of Truman
- Unit #
- A
- City
- KEY WEST
- Mile Marker
- 1
- Marathon Neighborhood
- N/A
- Side
- Median
- Flood Zone
- X
- Alternate Key #
- 1006564
- Parcel #
- 00006340-000000
- Zoning
- HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med
- Deed Restrictions
- No
- Legal
- KW PT LT 4 SQR 36 G9-593 OR153-170/71 OR377-65/66 OR773-1201 OR1097-1042/43 OR1298-1844/45 OR1432-2163/64 OR2272-2265
- Taxes
- 13468.4
- Tax Year
- 2025
- Pub Sewer HkUp
- Yes
Contract Information
- Listing Board
- Key West Association
- Potential Short Sale
- No
- Bank Owned
- No
General Property Description
- Realtor.COM Type
- Multi-family
- Style
- Condo
- Waterfront
- No
- Pool
- No
- Year Built
- 1889
- Lot SqFt
- 1704
- Living Apx SqFt
- 1082
- SqFt Source
- Seller
- Total Bedrooms
- 2
- Full Baths
- 2
- Half Baths
- Yes
- Total Baths
- 3
- Rentals Allowed
- With Restrictions
- Control Depth
- 0
- Total Units
- 0
Status Change Info
- Contingent
- Contingent/Show
Association Info
- Mandatory Home Owners Asc
- Yes
- Condo Doc's
- Yes
- 1st Right of Refusal
- Yes
- Association Fee $
- 0
Building Style
- Above Flood
- Yes
- Stories
- 2 Stories
- Conch
- Yes
More Information
Financial Status
- Auction
- No
- Bank Owned
- No
- Potential Short Sale
- No
Remarks & Misc
- Remarks – Consumer
- 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.
License Info
- Non Trans Rntl Lic
- Yes
Fee Includes
- Common Area Mnt
- Yes
Dockage
- None
- Yes
Tax Exemptions
- None
- Yes
Appliances
- Dishwasher
- Yes
- Disposal
- Yes
- Dryer
- Yes
- Freezer
- Yes
- Microwave
- Yes
- Oven
- Yes
- Refrigerator
- Yes
- Washer
- Yes
- Wine Cooler
- Yes
Pets
- Pets Allowed
- Yes
Cooling
- Ceiling Fans(s)
- Yes
- Central Air
- Yes
Waterfront
- None
- Yes
Waterview
- No Waterview
- Yes
Floor
- Wood
- Yes
Neighborhood Feature
- Beach
- Yes
- Bike Paths
- Yes
- Fire Hydrant
- Yes
Interior Features
- Built-in Cabinets
- Yes
- Drapes/Blinds Incl
- Yes
- Smoke Alarms
- Yes
- Walk-in Closet(s)
- Yes
- Window Treatments
- Yes
Windows/Doors
- Impact Rstnce Doors
- Yes
- Impact Rstnce Window
- Yes
- Wood Windows
- Yes
Construction
- Frame
- Yes
Land Size
- Less Than 1/4 Acre
- Yes
Furnished
- Furnished
- Yes
Terms
- Cash
- Yes
- Conventional
- Yes
Utilities
- Buyer to Verify
- Yes
- Elect Separate Meter
- Yes
- FKAA
- Yes
- Municipal Sewer
- Yes
- Water Separate Meter
- Yes
Porch/Balcony
- Open Porch/Balcony
- Yes
Exterior Features
- Privacy Wall/Fence
- Yes
Roof
- Metal Roof
- Yes
Shutters
- Other
- Yes
Property Features
Fee Includes:
Common Area Mnt
Tax Exemptions:
None
License Info:
Non Trans Rntl Lic
Waterfront:
None
Waterview:
No Waterview
Dockage:
None
Building Style:
Conch
Furnished:
Furnished
Cooling:
Ceiling Fans(s); Central Air
Utilities:
Buyer to Verify; Elect Separate Meter; FKAA; Municipal Sewer; Water Separate Meter
Interior Features:
Built-in Cabinets; Drapes/Blinds Incl; Smoke Alarms; Walk-in Closet(s); Window Treatments
Appliances:
Dishwasher; Disposal; Dryer; Freezer; Microwave; Oven; Refrigerator; Washer; Wine Cooler
Exterior Features:
Privacy Wall/Fence
Construction:
Frame
Shutters:
Other
Floor:
Wood
Roof:
Metal Roof
Pets:
Pets Allowed
Neighborhood Feature:
Beach; Bike Paths; Fire Hydrant
Land Size:
Less Than 1/4 Acre
Terms:
Cash; Conventional
Listing Office:
Truman & Co. (KW)
Last Updated: April - 13 - 2026
The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.