419 Simonton St, Unit A

1,123 Sq. Ft.
$1,322 / Sq. Ft.
1,123
Sq. Ft.
$1,322
per Sq. Ft.

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...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.
  1. Listed by Team Kaufelt • Truman & Co. (KW)

Property Details for 419 Simonton Street, Unit A

Waterfront
None
Waterfront
No
Zoning
HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med
Subdivision
Old Town - Unlisted (1.0)
Building Style
Conch
Pets
Pets Allowed

Open Houses

Sunday, Jan 25th

1:00 PM - 3:00 PM

Public

LISTING UPDATED: 01/22/2026 02:12 PM

Property Details for 419 Simonton Street, Unit A

StatusActive
MLS #618250
Days on Market1
Taxes$13,468 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeCondo
MLS TypeResidential / Condo
Year Built1889
CountyMonroe County

Location

Listing Courtesy of Truman & Co. (KW)
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Building Information for 419 Simonton Street, Unit A

Building/Complex419 Simonton StFloor-Stories2Residences-Pet PolicyAllowedPet Policy Details-Year Built1889

Payment Calculator

$8,360 per month

30 year fixed, 6.15% Interest

Principal and Interest

$7,238

Property Taxes

$1,122

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 419 Simonton Street, Unit A

Summary
Location and General Information
  • Waterview: No Waterview
  • Area: 02 - Key West
  • Absolute Longitude: 81.801594
  • Control Depth: 0
  • Listing Board: Key West Association
  • Side: Median
  • KW Neighborhood: Old Town-N of Truman
  • Mile Marker: 1.0
  • Marathon Neighborhood: N/A
  • Neighborhood Feature: Fire Hydrant, Bike Paths, Beach
  • Key/Island: Key West
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: Yes
  • Association Info: Condo Doc's: Yes
  • Association Info: 1st Right of Refusal: Yes
  • Fee Includes: Common Area Mnt
  • Furnished: Furnished
  • Tax Year: 2025
  • Tax Exemptions: None
Property
Lot Information
  • Parcel #: 00006340-000000
  • Land Size: Less Than 1/4 Acre
  • License Info: Non Trans Rntl Lic
Property and Assessments
  • 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
  • MLS Approved: Y
  • Bank Owned: No
  • SqFt Source: Seller
  • Flood Zone: X
  • Rentals Allowed: With Restrictions
  • Deed Restrictions: No
  • Picture Count: 28
  • Document Count: 0
  • Building Style: Above Flood: Yes
Utilities
  • Utilities: FKAA, Water Separate Meter, Elect Separate Meter, Buyer to Verify, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Pool: No
  • Porch/Balcony: Open Porch/Balcony
Interior and Exterior Features
Interior Features
  • Floor: Wood
  • Interior Features: Drapes/Blinds Incl, Window Treatments, Built-in Cabinets, Walk-in Closet(s), Smoke Alarms
  • Appliances: Washer, Wine Cooler, Freezer, Disposal, Microwave, Oven, Refrigerator, Dishwasher, Dryer
Exterior Features
  • Roof: Metal Roof
  • Shutters: Other
  • Construction: Frame
  • Dockage: None
  • Exterior Features: Privacy Wall/Fence
  • Windows/Doors: Wood Windows, Impact Rstnce Window, Impact Rstnce Doors

Property History for 419 Simonton Street, Unit A

DateEvent & SourcePriceAppreciation
Jan 22, 2026

Listed (Active)

FKMLS #618250

$1,485,000
DateEvent & SourcePrice
01/22/2026

Listed (Active)

FKMLS #618250

$1,485,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Schools near 419 Simonton Street, Unit A

This home is within Monroe.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - K to 12
Public - 9 to 12
Public - K to 5
Rating
School
Distance
Gerald Adams Elementary School
PublicPK to 5

Monroe Virtual Instruction Program
PublicK to 12

Key West High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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419 Simonton Street, Unit A is a condo for sale in Key West, FL 33040. This property was listed for sale on January 22, 2026 by Truman & Co. (KW), it's currently listed at $1,485,000. This listing's school district is Monroe. Nearby schools include Gerald Adams Elementary School, Monroe Virtual Instruction Program and Key West High School. 419 Simonton Street, Unit A is a 2-bed, 3-bath, 1,123 sqft condo built in 1889.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Truman & Co. (KW)

Based on information from one of the following Multiple Listing Services: Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.