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Amy Bruggeman

amy@americancaribbean.com +1(305) 619-0818

Listed by Team Kaufelt Truman & Co. (KW)

$ 1,375,000

Est. payment | -/mo

2 Beds

3 Baths

1,082 SqFt

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$ 1,375,000

Est. payment | -/mo

Save Virtual Tour

2 Beds

3 Baths

1,082 SqFt

Key Details

Property Type Condo

Sub Type Condominium

Listing Status Active Under Contract

Purchase Type For Sale

Square Footage 1,082 sqft

Price per Sqft $1,270

Subdivision Old Town - Unlisted (1.0)

MLS Listing ID 618250

Style Above Flood,Conch

Bedrooms 2

Full Baths 2

Half Baths 1

HOA Fees $1,343

HOA Y/N Yes

Year Built 1889

Annual Tax Amount $13,468

Tax Year 2025

Lot Size 1,704 Sqft

Acres 0.04

Property Sub-Type Condominium

Land Area 1082

Property 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.

Location

State FL

County Monroe

Community Fire Hydrant, Bike Paths, Beach

Area 02 - Key West

Zoning HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med

Interior

Interior Features Walk-in Closet(s), Built-in Cabinets, Drapes/Blinds Incl, Smoke Alarms, Window Treatments

Cooling Central Air, Ceiling Fans(s)

Flooring Wood

Furnishings Furnished

Window Features Impact Rstnce Doors,Impact Rstnce Window,Wood Windows,Shutters

Appliance Freezer, Dryer, Washer, Dishwasher, Disposal, Microwave, Oven, Wine Cooler, Refrigerator

Exterior

Exterior Feature Privacy Wall/Fence

Community Features Fire Hydrant, Bike Paths, Beach

Utilities Available Electric Separate Meter, FKAA, Municipal Sewer, Water Separate Meter, Buyer To Verify

Waterfront Description None

Roof Type Metal Roof

Porch Open Porch/Balcony

Garage No

Building

Architectural Style Above Flood, Conch

Others

HOA Fee Include Common Area Mnt

Tax ID 00006340-000000

Acceptable Financing Cash, Conventional

Listing Terms Cash, Conventional

Pets Allowed Yes

Virtual Tour https://mls.ricoh360.com/4a8b81ac-3ddb-491b-94da-ca87dea3fac2

419 Simonton ST Key West, FL 33040

Amy Bruggeman

Key Details

Location

Interior

Exterior

Building

Others

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419 Simonton ST