Listing Board: Key West Association

Potential Short Sale: No

Bank Owned: No

Current Price: $4,990,000

Listing Date: 2026-01-12

List Price: $4,990,000

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

Taxes: 31381

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

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 – Consumer: KEY WEST'S UNLIKELY SANCTUARY | DUAL TRANSIENT LICENSES 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.

Directions: Simonton St. between Petronia St. & Angela St.

Mandatory Home Owners Asc: No

1st Right of Refusal: No

Association Fee $: 0

# of City License: 2

Transient Rntl Licns: Yes

None: 1

None: 1

None: 1

Dishwasher: 1

Dryer: 1

Freezer: 1

Microwave: 1

Range: 1

Refrigerator: 1

Washer: 1

Wine Cooler: 1

Pets Allowed: 1

Ceiling Fans(s): 1

Central Air: 1

None: 1

No Waterview: 1

Tile: 1

Wood: 1

Built-in Cabinets: 1

Drapes/Blinds Incl: 1

Pantry: 1

Storage: 1

Walk-in Closet(s): 1

Window Treatments: 1

Updated/Remodeled: 1

Guest/Servant Qtrs: Legal

Above Flood: Unknown

Stories: 2 Stories

Aluminum Windows: 1

Glass Doors: 1

Sliding Glass Doors: 1

Car(s): 2

Off Street Parking: 1

Electric Gate: 1

CBS: 1

Combo Construction: 1

Concrete: 1

Less Than 1/4 Acre: 1

Cash: 1

Conventional: 1

Buyer to Verify: 1

FKAA: 1

Municipal Sewer: 1

Open Porch/Balcony: 1

Patio: 1

Detached Guest Qtrs: 1

Lighting: 1

Outdoor Shower: 1

Privacy Wall/Fence: 1

Storage: 1

Water Display: 1

In Ground: 1

Heated: Yes

Concrete: 1

Metal Roof: 1

Bank Owned: No

Potential Short Sale: No

Status: Active