Skip main navigation
For sale
$4,950,000
4beds
2,441sqft

720D Simonton St, Key West, FL 33040

4beds
2,441sqft
Single Family Residence
Built in 2008
5,220 Square Feet Lot
$2,028/sqft

What's special

Warm mid-century touchesThoughtfully curated interiorsSerene private courtyardHeated pool oasisFour bedroomsAmple off-street parkingStriking modern aesthetic

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
Source: FLKMLS,MLS#: 621632MLS Logo
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:

Listed by:

The Spottswood Team 305-432-4848,

Truman & Co. (KW),

Terri Spottswood 305-587-3407,

Truman & Co. (KW)

Source: FLKMLS,MLS#: 621632MLS Logo

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

DateEventPrice
10/14/2026Listed for sale$4,950,000-0.8%$2,028/sqft
Source: FLKMLS #621632 Report a problem
5/19/2026Listing removed$4,990,000$2,044/sqft
Source: Key West AOR #618363 Report a problem
1/28/2026Listed for sale$4,990,000+6.2%$2,044/sqft
Source: Key West AOR #618363 Report a problem
8/4/2022Sold$4,700,000$1,925/sqft
Source: FLKMLS #602118 Report a problem

Public tax history

Tax history is unavailable.

Monthly payment

Est. payment
$30,493/mo
Principal & interest
$27111
Property taxes
$3382
More affordability toolsChevron Right

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®️.

Neighborhood: Old Town

Nearby schools

Horace O'bryant School
Grades PK-8 • 0.9 miles
3/10
GreatSchools® Rating
Test Score Rating
3/10
Student Progress Rating
3/10
Key West High School
Grades 9-12 • 1.5 miles
3/10
GreatSchools® Rating
Test Score Rating
3/10
College Readiness Rating
5/10
Student Progress Rating
2/10