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$4,950,000
Key West, FL 33040
MLS# 621632
4 beds | 4 baths | 2441 sqft
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Property Description
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.
Details
Maps
Contract Information
Listing Board: Key West Association
Potential Short Sale: No
Bank Owned: No
Current Price: $4,950,000
Listing Date: 2026-10-14
List Price: $4,950,000
Location, Tax & Legal
KW Neighborhood: Old Town-N of Truman
City: KEY WEST
Mile Marker: 1
Marathon Neighborhood: N/A
Side: Median
Flood Zone: X FLOOD ZONE
Alternate Key #: 1016268
Add'l Parcel #1: 00015880-000000
Zoning: HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med
Deed Restrictions: Unknown
Legal: KW PT LOT 3 SQR 2 TR 4 OR172-109/10 OR190-476/77 OR333-396/97 OR610-518/19
Taxes: 32509.9
Tax Year: 2025
Pub Sewer HkUp: Yes
Street #: 720D
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
General Property Description
Realtor.COM Type: Residential - Single Family
Waterfront: No
Control Depth: 0
Lot SqFt: 5220
Pool: Yes
Lot Sqft Source: Property Data Card
Total Units: 2
SqFt Source: Property Data Card
Rentals Allowed: Yes
Min Rental Days: 1
Style: Single Family
Year Built: 2008
Living Apx SqFt: 2441
Total Bedrooms: 4
Full Baths: 4
Total Baths: 4
Remarks & Misc
Remarks – Consumer: 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.
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0
License Info
# of City License: 2
Transient Rntl Licns: Yes
Fee Includes
None: 1
Dockage
None: 1
Tax Exemptions
None: 1
Appliances
Dishwasher: 1
Dryer: 1
Freezer: 1
Microwave: 1
Range: 1
Refrigerator: 1
Washer: 1
Wine Cooler: 1
Pets
Pets Allowed: 1
Cooling
Ceiling Fans(s): 1
Central Air: 1
Waterfront
None: 1
Waterview
No Waterview: 1
Floor
Tile: 1
Wood: 1
Interior Features
Built-in Cabinets: 1
Drapes/Blinds Incl: 1
Pantry: 1
Storage: 1
Walk-in Closet(s): 1
Window Treatments: 1
Property Condition
Updated/Remodeled: 1
Specialty Rooms
Guest/Servant Qtrs: Legal
Building Style
Above Flood: Unknown
Stories: 2 Stories
Windows/Doors
Aluminum Windows: 1
Glass Doors: 1
Sliding Glass Doors: 1
Vehicle Storage
Car(s): 2
Off Street Parking: 1
Security
Electric Gate: 1
Construction
CBS: 1
Combo Construction: 1
Concrete: 1
Land Size
Less Than 1/4 Acre: 1
Terms
Cash: 1
Conventional: 1
Utilities
Buyer to Verify: 1
FKAA: 1
Municipal Sewer: 1
Porch/Balcony
Open Porch/Balcony: 1
Patio: 1
Exterior Features
Detached Guest Qtrs: 1
Lighting: 1
Outdoor Shower: 1
Privacy Wall/Fence: 1
Storage: 1
Water Display: 1
Pool Info
In Ground: 1
Heated: Yes
Concrete: 1
Roof
Metal Roof: 1
Financial Status
Bank Owned: No
Potential Short Sale: No
Status Change Info
Status: Active
Property Features
Fee Includes: None
Tax Exemptions: None
Waterfront: None
Waterview: No Waterview
Dockage: None
Property Condition: Updated/Remodeled
Vehicle Storage: Off Street Parking
Cooling: Ceiling Fans(s); Central Air
Utilities: Buyer to Verify; FKAA; Municipal Sewer
Interior Features: Built-in Cabinets; Drapes/Blinds Incl; Pantry; Storage; Walk-in Closet(s); Window Treatments
Appliances: Dishwasher; Dryer; Freezer; Microwave; Range; Refrigerator; Washer; Wine Cooler
Exterior Features: Detached Guest Qtrs; Lighting; Outdoor Shower; Privacy Wall/Fence; Storage; Water Display
Pool Info: In Ground; Concrete
Construction: CBS; Combo Construction; Concrete
Floor: Tile; Wood
Roof: Metal Roof
Pets: Pets Allowed
Security: Electric Gate
Land Size: Less Than 1/4 Acre
Terms: Cash; Conventional
Listing Office: Truman & Co. (KW)
Last Updated: October - 14 - 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.
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