Old Town has plenty of history. What it rarely has is a brand-new secret. Privately positioned behind one of Simonton Street's most storied facades, 419 Simonton Street C is a freestanding 2026 residence with no shared walls and a world of its own. Fully furnished with a curated interiors package by Ben Teague Design, this two-bedroom, two-and-a-half-bath home pairs clean-lined architecture with the relaxed rhythm of Key West. Cathedral ceilings elevate both bedrooms, while impact-rated windows and doors, wood flooring, built-in cabinetry, walk-in closets and thoughtful finishes bring refinement and ease to the approximately 1,409-square-foot interior. At the center of the home, a streamlined kitchen featuring Fisher & Paykel and Bosch appliances, a walk-in pantry and under-cabinet lighting is designed to transition effortlessly from morning coffee to evening cocktails. Outdoors, vibrant tropical landscaping surrounds a private heated pool with a tranquil water feature, secluded patio and outdoor shower. Dedicated parking for a golf cart or small vehicle, separate utility meters, a metal roof and an X flood-zone location provide the practical advantages buyers rarely find in Old Town. Part of an intimate three-residence setting, Unit C offers the privacy of a standalone home, the simplicity of condominium ownership and convenient access to Old Town's celebrated restaurants, galleries, waterfront and nightlife. Entirely new, quietly hidden and ready to enjoy from day one.
The historic neighborhood commercial district Truman/Simonton HNC-1 consists of Simonton, Truman Avenue, and White Street South Corridors. The HNC-1 district is located along major segments of Simonton Street, from Caroline South to United Street; Truman Avenue, from Simonton Street northeast to White Street; and White Street, from Truman Avenue south to United Street; and generally includes larger scale commercial uses oriented toward the motoring public.
Permitted uses
Include but are not limited to:
Religious facility
Commercial & retail
Hospital / medical center
Housing-Group
Housing-Single unit
Housing-Multiple units
Hotel / motel
Office
Veterinary clinic
Park & open space
Climate risks
3/10 Flood Factor
Estimated 10-16% chance of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
Heat Factor
We're working on getting current and accurate heat risk information for this home.
10/10 Wind Factor
99% chance of strong winds in next 30 years
1/10 Air Factor
0 unhealthy days expected this year, 0 days in 30 years
Provided by First Street
Historical weather
Key West, FL • 33040
Average low and high temperatures (°F)
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69
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Sun exposure
86/ 100
Very good sunlight
Sunscore
This home receives average direct sun exposure in Key West. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
8.3 hrs
5.8 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 419 Simonton St Unit c
$1,958,435
$37K under list price of $2.00M
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $1.3M to $2.1M.