421 - 423 Simonton Street, Key West, FL 33040
$5,850,000
Property Type:
Residential
Bedrooms:
6
Baths:
8
Square Footage:
3,010
Lot Size (sq. ft.):
3,520
Status:
Active
Current Price:
$5,850,000
List Date:
4/08/2025
Last Modified:
12/09/2025
Description
Two Transient Homes Now Available For Sale. Just one block off world-famous Duval Street, this rare property offers two homes - each 3 bedrooms, 3.5 baths and private pools. These have strong rental histories. These well-appointed residences blend island charm with modern comfort, featuring open-concept living areas, updated kitchens and private ensuite bedrooms. Thoughtfully designed for guest privacy and relaxation, each home includes its own outdoor lounging space and pool—perfect for cooling off after a day in the sun or enjoying a quiet evening under the palms.
Whether you're looking for a investment opportunity, a vacation retreat with rental flexibility, or a mix of both, this unique setup delivers unmatched versatility just steps from the vibrant restaurants, galleries, and nightlife of Duval Street.
More Information MLS# 614546
Contract Information
Listing Board: Key West Association
As is Rght to Inspct: Yes
Species List: No
Current Price: $5,850,000
Listing Date: 2025-04-08
List Price: $5,850,000
Location, Tax & Legal
KW Neighborhood: Old Town-N of Truman
City: KEY WEST
Off Shore Island: No
Mile Marker: 1
Marathon Neighborhood: N/A
Side: Median
Flood Zone: X
Alternate Key #: 1006581
Parcel #: 00006360-000000
Zoning: HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med
Deed Restrictions: Unknown
Legal: KW PT LOT 4 SQR 36 G12-444/45 OR564-150 OR1176-1632/33 OR2799-1921/22 OR2799-1925/26
Taxes: 26522.53
Tax Year: 2024
Pub Sewer HkUp: Yes
Street #: 421 - 423
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: Multi-family
Waterfront: No
Control Depth: 0
Lot Size: 44 x 80
Lot SqFt: 3520
Pool: Yes
Total Units: 2
Acres: 0.08
SqFt Source: Property Data Card
Rentals Allowed: Yes
Min Rental Days: 3
Style: Duplex
Year Built: 2020
Living Apx SqFt: 3010
Total Bedrooms: 6
Full Baths: 6
Half Baths: 2
Total Baths: 8
Remarks & Misc
Remarks – Consumer: Two Transient Homes Now Available For Sale. Just one block off world-famous Duval Street, this rare property offers two homes - each 3 bedrooms, 3.5 baths and private pools. These have strong rental histories. These well-appointed residences blend island charm with modern comfort, featuring open-concept living areas, updated kitchens and private ensuite bedrooms. Thoughtfully designed for guest privacy and relaxation, each home includes its own outdoor lounging space and pool—perfect for cooling off after a day in the sun or enjoying a quiet evening under the palms.
Whether you're looking for a investment opportunity, a vacation retreat with rental flexibility, or a mix of both, this unique setup delivers unmatched versatility just steps from the vibrant restaurants, galleries, and nightlife of Duval Street.
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
Dryer: 1
Microwave: 1
Oven: 1
Range: 1
Refrigerator: 1
Stainless Steel Appliance(s): 1
Washer: 1
Pets
Pets Allowed: 1
Cooling
Ceiling Fans(s): 1
Central Air: 1
Waterfront
None: 1
Waterview
No Waterview: 1
Interior Features
Built-in Cabinets: 1
Smoke Alarms: 1
Building Style
Above Flood: Yes
Stories: 2 Stories
Construction
Combo Construction: 1
Land Size
Less Than 1/4 Acre: 1
Furnished
Negotiable: 1
Utilities
FKAA: 1
Municipal Sewer: 1
Porch/Balcony
Deck: 1
Open Porch/Balcony: 1
Exterior Features
Privacy Wall/Fence: 1
Pool Info
In Ground: 1
Pre-Wired
Cable: 1
Roof
Metal Roof: 1
Status Change Info
Status: Active
Property Features
Fee Includes: None
Tax Exemptions: None
Waterfront: None
Waterview: No Waterview
Dockage: None
Furnished: Negotiable
Cooling: Ceiling Fans(s); Central Air
Utilities: FKAA; Municipal Sewer
Interior Features: Built-in Cabinets; Smoke Alarms
Pre-Wired: Cable
Appliances: Dryer; Microwave; Oven; Range; Refrigerator; Stainless Steel Appliance(s); Washer
Exterior Features: Privacy Wall/Fence
Pool Info: In Ground
Construction: Combo Construction
Roof: Metal Roof
Pets: Pets Allowed
Land Size: Less Than 1/4 Acre
Listing Office:
Berkshire Hathaway HomeServices Knight & Gardner Realty
Last Updated: December - 09 - 2025
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.