720D Simonton Street, Key West, FL 33040

New Listing

$4,950,000

Virtual Tour

https://www.zillow.com/view-imx/086180de-0e71-499d-937e-211050f129d8?setAttribution=mls&wl=true&initialViewType=pano&utm_source=dashboard

Front Guesthouse - Laundry Area 2nd Floor

Front Guesthouse - Ensuite Bathroom 2nd Floor

Rear Guesthouse - Ensuite Bathroom w/ Soaking Tub

Rear Guesthouse - Ensuite Bathroom w/ Walk-in Shower

Contra House Exterior_26-09-28_Filip_015

Modern & Private 1 block from Duval Street!

Property Type: Residential Bedrooms: 4 Baths: 4 Square Footage: 2,441 Lot Size (sq. ft.): 5,220 Status: Active

Current Price: $4,950,000 List Date: 10/14/2026 Last Modified: 10/16/2026

Overview

Description

DUAL TRANSIENT LICENSES | A RARE DEPARTURE FROM THE ORDINARY 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 landscapin ... (Read more)

Listing Details MLS# 621632

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
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 OR610-518/19
Taxes: 32509.9
Tax Year: 2025
Pub Sewer HkUp: Yes

Contract Information

Listing Board: Key West Association
Potential Short Sale: No
Bank Owned: No

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: Yes
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: Unknown
Stories: 2 Stories

Vehicle Storage

Car(s): 2
Off Street Parking: Yes

Specialty Rooms

Guest/Servant Qtrs: Legal

Pool Info

Heated: Yes
In Ground: Yes
Concrete: Yes

Financial Status

Bank Owned: No
Potential Short Sale: No

Remarks & Misc

Remarks – Consumer: DUAL TRANSIENT LICENSES | A RARE DEPARTURE FROM THE ORDINARY 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.

Fee Includes

None: Yes

Dockage

None: Yes

Tax Exemptions

None: Yes

Appliances

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

Pets

Pets Allowed: Yes

Cooling

Ceiling Fans(s): Yes
Central Air: Yes

Waterfront

None: Yes

Waterview

No Waterview: Yes

Floor

Tile: Yes
Wood: Yes

Interior Features

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

Property Condition

Updated/Remodeled: Yes

Windows/Doors

Aluminum Windows: Yes
Glass Doors: Yes
Sliding Glass Doors: Yes

Security

Electric Gate: Yes

Construction

CBS: Yes
Combo Construction: Yes
Concrete: Yes

Land Size

Less Than 1/4 Acre: Yes

Terms

Cash: Yes
Conventional: Yes

Utilities

Buyer to Verify: Yes
FKAA: Yes
Municipal Sewer: Yes

Porch/Balcony

Open Porch/Balcony: Yes
Patio: Yes

Exterior Features

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

Roof

Metal Roof: Yes

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: October - 16 - 2026

Broker Attribution: 3054324848

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.

Search powered by FBS Products