421 - 423 Simonton Street, Key West, FL 33040 (MLS# 614546)

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

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