720D Simonton Street, Key West, FL 33040

$4,990,000
Property Type: Residential Bedrooms: 4 Baths: 4 Square Footage: 2,441 Lot Size (sq. ft.): 5,220 Status: Active
Current Price: $4,990,000 List Date: 1/28/2026 Last Modified: 2/12/2026

Description

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.

More Information MLS# 618363

Contract Information

Current Price: $4,990,000 Listing Date: 2026-01-12 Listing Board: Key West Association List Price: $4,990,000 Potential Short Sale: No Bank Owned: No

Location Tax Legal

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 Style: Single Family Waterfront: No Pool: Yes Year Built: 2008 Total Units: 2 Lot SqFt: 5220 Lot Sqft Source: Property Data Card Living Apx SqFt: 2441 SqFt Source: Property Data Card Total Bedrooms: 4 Full Baths: 4 Total Baths: 4 Rentals Allowed: Yes Min Rental Days: 1

Status Change Info

Status: Active

Association Info

Mandatory Home Owners Asc: No 1st Right of Refusal: No

License Info

# of City License: 2 Transient Rntl Licns: Yes

Building Style

Above Flood: Unknown Stories: 2 Stories

Vehicle Storage

Car(s): 2

Specialty Rooms

Guest/Servant Qtrs: Legal

Pool Info

Heated: Yes

Financial Status

Bank Owned: No Potential Short Sale: No

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: February - 12 - 2026
Broker Attribution: 305-587-3407

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