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:
4/01/2026
Overview
Description
Listing Details MLS# 614546
Location, Tax & Legal
- 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
- 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
Contract Information
- Listing Board
- Key West Association
- As is Rght to Inspct
- Yes
- Species List
- No
General Property Description
- Realtor.COM Type
- Multi-family
- Style
- Duplex
- Waterfront
- No
- Pool
- Yes
- Year Built
- 2020
- Total Units
- 2
- Lot SqFt
- 3520
- Acres
- 0.08
- Living Apx SqFt
- 3010
- SqFt Source
- Property Data Card
- Total Bedrooms
- 6
- Full Baths
- 6
- Half Baths
- 2
- Total Baths
- 8
- Rentals Allowed
- Yes
- Min Rental Days
- 3
- Control Depth
- 0
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
More Information
Building Style
- Above Flood
- Yes
- Stories
- 2 Stories
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.
Fee Includes
- None
- Yes
Dockage
- None
- Yes
Tax Exemptions
- None
- Yes
Appliances
- Dryer
- Yes
- Microwave
- Yes
- Oven
- Yes
- Range
- Yes
- Refrigerator
- Yes
- Stainless Steel Appliance(s)
- Yes
- Washer
- Yes
Pets
- Pets Allowed
- Yes
Cooling
- Ceiling Fans(s)
- Yes
- Central Air
- Yes
Waterfront
- None
- Yes
Waterview
- No Waterview
- Yes
Interior Features
- Built-in Cabinets
- Yes
- Smoke Alarms
- Yes
Construction
- Combo Construction
- Yes
Land Size
- Less Than 1/4 Acre
- Yes
Furnished
- Negotiable
- Yes
Utilities
- FKAA
- Yes
- Municipal Sewer
- Yes
Porch/Balcony
- Deck
- Yes
- Open Porch/Balcony
- Yes
Exterior Features
- Privacy Wall/Fence
- Yes
Pool Info
- In Ground
- Yes
Pre-Wired
- Cable
- Yes
Roof
- Metal Roof
- Yes
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: April - 01 - 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.