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  • 720D Simonton Street, Key West, FL 33040 (MLS# 618363)

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

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

Location, Tax & Legal

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

General Property Description

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 & Misc

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.

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

Dishwasher: 1 Dryer: 1 Freezer: 1 Microwave: 1 Range: 1 Refrigerator: 1 Washer: 1 Wine Cooler: 1

Pets

Pets Allowed: 1

Cooling

Ceiling Fans(s): 1 Central Air: 1

Waterfront

None: 1

Waterview

No Waterview: 1

Floor

Tile: 1 Wood: 1

Interior Features

Built-in Cabinets: 1 Drapes/Blinds Incl: 1 Pantry: 1 Storage: 1 Walk-in Closet(s): 1 Window Treatments: 1

Property Condition

Updated/Remodeled: 1

Specialty Rooms

Guest/Servant Qtrs: Legal

Building Style

Above Flood: Unknown Stories: 2 Stories

Windows/Doors

Aluminum Windows: 1 Glass Doors: 1 Sliding Glass Doors: 1

Vehicle Storage

Car(s): 2 Off Street Parking: 1

Security

Electric Gate: 1

Construction

CBS: 1 Combo Construction: 1 Concrete: 1

Land Size

Less Than 1/4 Acre: 1

Terms

Cash: 1 Conventional: 1

Utilities

Buyer to Verify: 1 FKAA: 1 Municipal Sewer: 1

Porch/Balcony

Open Porch/Balcony: 1 Patio: 1

Exterior Features

Detached Guest Qtrs: 1 Lighting: 1 Outdoor Shower: 1 Privacy Wall/Fence: 1 Storage: 1 Water Display: 1

Pool Info

In Ground: 1 Heated: Yes Concrete: 1

Roof

Metal Roof: 1

Financial Status

Bank Owned: No Potential Short Sale: No

Status Change Info

Status: Active

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

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.

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