DUAL TRANSIENT LICENSES | A RARE DEPARTURE FROM THE ORDINARY While most Old Town properties embrace tropical pastels and wooden shutters, this exceptional compound stands as a bold architectural departure. With its striking modern aesthetic, raw concrete elements, and serene private courtyard, this is where minimalist design meets maximum investment potential, just one block from Duval Street. | THE COMPOUND | Built in 2008 on a generous 5,220sf lot, this 2,441sf property features two distinct units, a front house and back house, connected by a heated pool oasis. Four bedrooms, four full baths, soaring two-story ceilings, and thoughtfully curated interiors showcase warm mid-century touches against clean architectural lines. Wood and tile floors, built-in cabinetry, walk-in closets, and abundant natural light through expansive glass doors create spaces that are both meditative and functional. | THE SANCTUARY | High privacy walls enclose a tranquil pool courtyard with tropical landscaping, outdoor shower, and ample off-street parking. Electric gate entry ensures complete seclusion while downtown's energy pulses just steps away. | THE OPPORTUNITY | Two active transient rental licenses with 1-day minimum stays unlock exceptional income in Key West's most sought-after location. The property's distinctive design aesthetic attracts discerning guests seeking something different, proven by outstanding reviews and strong rental performance. HNC zoning supports flexible commercial use, while X flood zone designation offers insurance advantages. | THE LOCATION | Heart of Old Town, steps from Duval's legendary dining, nightlife, galleries, and waterfront. Close enough to all the action, far enough from the noise. This is investment-grade real estate with soul, where architectural distinction drives premium rates and occupancy.
Single-familyProperty Type
2008Year Built
5,220 sq ftLot Size
$2,028Price/Sq.Ft.
2 spacesParking
Listed by The Spottswood Team Team• Truman & Co. (KW)
* * FOR STATISTICAL PURPOSES ONLY * * Private Old Town compound with 2 transient licenses located 1 block from Duval Street. 2 units, 4BD/4BA total, 2,441 SF total, 5,220 SF Lot, pool, tropical landscaping, off street parking.
As the MLS and public records start to fill up, we'll list the details here.
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
Minimal risk 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
80/ 100
Very good sunlight
Sunscore
There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
7.9 hrs
5.3 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 720D Simonton St
$4,800,589
$149K under list price of $4.95M
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $1.7M to $3.7M.