720D Simonton St, Key West, FL 33040
What's special
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.
- 2 days
- 732
- 24
Travel times
Dining Room Guesthouse #1
Living Room Guesthouse #1
Kitchen Guesthouse #1
Bedroom 1st Floor - Guesthouse #1
Bathroom 1st Floor - Guesthouse #1
Bedroom 2nd Floor - Guesthouse #1
Bathroom 2nd Floor - Guesthouse #1
Balcony Guesthouse #1
Living Room Guesthouse #2
Dining Room Guesthouse #2
Kitchen Guesthouse #2
Bedroom #1 - Guesthouse #2
Bathroom #1 - Guesthouse #2
Bedroom #2 - Guesthouse #2
Bathroom #2 - Guesthouse #2
Zillow last checked:
Listing updated:
The Spottswood Team 305-432-4848,
Truman & Co. (KW),
Terri Spottswood 305-587-3407,
Truman & Co. (KW)
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 4
Cooling
- Central Air, Ceiling Fans(s)
Appliances
- Included: Washer, Dryer, Dishwasher, Refrigerator, Range, Microwave, Freezer, Wine Cooler
Features
- Built-in Features, Storage, Walk-in Closet(s)
- Flooring: Tile, Wood
Interior area
- Total structure area: 2,441
- Total interior livable area: 2,441 sqft
Video & virtual tour
Property
Features
- Patio & porch: Open Porch/Balcony, Patio
- Exterior features: Lighting, Outdoor Shower, Storage, Water Display
- Has private pool: Yes
- Pool features: In Ground, Concrete
- Fencing: Privacy
Lot
- Size: 5,220 Square Feet
Details
- Additional structures: Guest House
- Additional parcels included: 00015880-000000
- Zoning: HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- CBS, Concrete, Combo Construction
Condition
- Updated/Remodeled
- New construction: No
- Year built: 2008
Community & HOA
Community
- Security: Security Gate
- Subdivision: Old Town - Unlisted (1.0)
HOA
- Has HOA: No
- Services included: None
Location
- Region: Key West
Financial & listing details
- Price per square foot: $2,028/sqft
- Annual tax amount: $32,509
- Date on market: 10/14/2026
- Listing terms: Cash,Conventional
Price history
| Date | Event | Price |
|---|---|---|
| 10/14/2026 | Listed for sale | $4,950,000-0.8%$2,028/sqft |
Source: | ||
| 5/19/2026 | Listing removed | $4,990,000$2,044/sqft |
Source: | ||
| 1/28/2026 | Listed for sale | $4,990,000+6.2%$2,044/sqft |
Source: | ||
| 8/4/2022 | Sold | $4,700,000$1,925/sqft |
Source: | ||
Public tax history
Monthly payment
Estimated market value
Not available
Estimated sales range
Not available
Not available
Climate risks
Explore flood, wildfire, and other predictive climate risk information for this property on First Street®️.